Related to ECF Nos. 4, 75, 516, 923, & 938
MEMORANDUM OPINION
I. JURISDICTION, AUTHORITY, AND VENUE... 355
II. PRELIMINARY MATTERS... 356
A. Factual and Computation Stipulations of the Parties... 356
B. Facts Found Due to this Court’s Application of Collateral Estoppel... 356
C. United States’ Motion to Exclude the Expert Report, Opinions, and Testimony of Joshua S. Rubenstein... 358
D. Dee’s Motion for Partial Summary Judgment... 366
III. FACTUAL AND PROCEDURAL HISTORY... 366
IV. LEGAL ANALYSIS... 374
A. Burden of Proof... 374
1. Bankruptcy Law Burden of Proof— In General... 374
a) Prima Facie Validity under Bankruptcy Rule 3001(f)... 375
b) Have the Debtors Raised Evidence of a Probative Force Equal to that of the Proofs of Claim?... 378
2. Tax Law Burden of Proof — -In General ... 380
a) Gift Tax Deficiencies and the Presumption of Correctness... 380
*353 (1) Is the IRS’ Determination “Arbitrary and Erroneous?”... 381
(2) Burden Shifting under 26 U.S.C. § 7491... 383
b) Fraud Penalties for Income Tax and Gift Tax Underpayments... 386
c) International Failure to File Penalties ... 387
3.The Debtors’ Defenses... 388
a) Reasonable Cause Defenses... 388
b) Dee’s Innocent Spouse Defense... 389
B.Was the Debtors’ Underpayment of Income Taxes Due to Fraudulent Intent?... 389
1.Relevant Statutes and Badges of Fraud... 392
a) The Complexity of the Offshore System... 394
b) The Wylys’ Willingness to Commit Securities Fraud to Preserve the Secret Offshore System and to Maintain its Tax Advantages... 408
c) The Failure to Take Action to Resolve the Conflicting Advice Sam and Charles Received Regarding the 1992 IOM Trusts... 413
d) The Creation of False Documents to Support the Settling of IOM Trusts in 1994 and 1995 to Attempt to Obtain Favorable Tax Benefits for the Wy-lys... 415
e) The Treatment of the Offshore System as the Wyly Family Piggy Bank.423
f) The Planned Insolvency of Various IOM Corporations that Owed Annuity Obligations... 431
g) Understatement of Income..'. 441
h) Concealment of Income or Assets ... 446
i) Offering False or Incredible Testimony. .. 447
j) Offering Implausible or Inconsistent Explanations of Behavior... 449
k) Filing False Documents... 452
l) Failure to Cooperate with Taxing Authorities... 460
C. Was Dee Willfully Blind?... 461
D. Is Dee Entitled to the Benefits of the Innocent Spouse Defense?... 464
E. Did Sam Establish his Reasonable Cause Defense to the Imposition of Fraud Penalties for His Income Tax Underpayments? ... 475
1. The Defense in General... 475
2. The 1992 Private Annuity Transactions ... 482
3. The Settlement of the Bessie IOM Trust and the La Fourche IOM Trust and their Proper Characterization... 494
4. The 1996 Private Annuity Transactions ... 498
5. Alleged Reliance on French... 503
F. Were Gifts Made to the Wylys’ Children?... 512
1. The Relevant Standards... 513
a) Defining a Gift... 513
b) Determining the Underlying Substance of the Transaction... 514
(1) The Economic Substance Doctrine. .. 514
(2) The Substance Over Form Doctrine. .. 515
(3) The Step Transaction Doctrine. .. 515
2. Understanding the Transactions Alleged to be Gifts by Sam to His .Children ... 516
a) Formation and Funding of the Cayman LLCs... 516
b) The Real Estate Holdings... 519
*354 c) Liquidation of the Cayman LLCs... 524
3. Analysis of Alleged Gifts Made by Sam... 524
a) Cash Used to Purchase, Improve, and Maintain the Cottonwood Ventures I and II Properties... 525
b) Cash and Other Assets that were Transferred Into the Cayman LLCs... 532
(1) The Interests in IOM Real Estate Companies... 532
(2) Cash and Other Financial Assets Transferred to the Cayman LLCs... 535
4. Understanding the Transactions Alleged to be Gifts by Dee to Her Children ... 536
c) Stargate Horse Farm... 537
d) Little Woody (LL Ranch)... 538
5. Analysis of the Alleged Gifts Made by Dee.,. 539
a) Cash Used for the Purchase, Maintenance, Improvement, and Upkeep of the Stargate Horse Farm and Little Woody (LL Ranch) Real Estate Properties ... 539
b) The Promissory Note Due to Dee from the Caroline D. Wyly Irrevocable Trust... 543
(1) Overview of the Transaction... 543
(2) Analysis of the Alleged Gift Made by Dee... 546
(3) Is Dee Liable for Fraud Penalties on her Gift?... 549
G.Are Penalties Owing for the Failure to File Forms 3520, 3520-A, and 5471?... 551
1. Introduction... 551
2. Statutory Overview... 551
a)§ 6038 and Failures to File Form 5471... 553
b) § 6048(b) and Failures to File Form 3520-A... 556
c) § 6048(c) and Failures to File Form 3520... 557
(1) In General... 557
(2) Annuity Payments. <. 558
(3) Real Estate Transactions... 569
(4) Security Capital Loans... 570
(5) Sales of Options to IOM Corporations ... 575
H. Did the Debtors Establish Their Reasonable Cause Defenses to the Imposition of International Penalties?... 576
I. Introduction... 576
a) Review of Provisions of § 6038... 576
b) Review of Provisions of §§ 6048(b) and 6677... 576
2. Reasonable Cause and Lack of Willful Neglect... 577
a) In General... 577
b) Reliance on the Advice of Professionals ... 579
c) Honest Difference of Opinion... 580
d) Application to Both Debtors... 583
(1) As to Sam... 585
(2) As to Dee... 593
I. Does the Imposition of the International Penalties Violate the Eighth Amendment? ... 602
1. Applicable Supreme Court Precedent. .. 602
a) The Supreme Court Decisions... 603
b) Lower Courts’ Interpretations of Supreme Court Precedent.. .608
2. Are the International Penalties “Fines”?... 609
3. Alternatively, Are the International Penalties.“Excessive?”.., 614
a) As to Sam... 616
*355 b) As to Dee... 621
J. Do the Equitable Doctrines of Lach-es or Estoppel Apply Here, or Does the Court have Discretion Regarding the Assessment of Taxes or Penalties Against the Debtors?... 624
1. Does Laches Apply Here?... 624
2. Does Estoppel Apply Here?... 627
3. Does the Court have Discretion to Alter the Penalty Amounts?... 634
K. Suspension of Interest Under 26 U.S.C. § 6404(g)... 635
1. This Court has Jurisdiction to Determine the Amount of Interest Payable by the Debtors, Including Whether the Debtors Are Entitled to Mandatory Interest Suspension under 26 U.S.C. § 6404(g)... 636
2. Mandatory Suspension of Interest Does Not Apply in Any Case Involving Fraud, Precluding Suspension for Sam in the Relevant Years... 638
3. Interest Suspension is Moot as to Dee Because She Did Not Commit Tax Fraud and She is Entitled to Innocent Spouse Relief from the Income Tax Underpayments to Which § 6404(g) Interest Suspension Would Apply... 639
V. CONCLUSION... 639
Before the Court are the Motion Pursuant to Bankruptcy Code § 505 to Determine Tax Liability, If Any [ECF No. 4] and the Amended Motion Under Bankruptcy Code Section 505 to Determine Tax Liability, If Any [ECF No. 516] (together, the “Motions”) filed by Samuel Evans Wyly (“Sam”) and Carolyn Dee Wyly (“Dee,” and together with Sam, the “Debtors”), respectively, in which the Debtors seek to have this Court determine the allowed claim of the Internal Revenue Service (“IRS”) against them. The Debtors have also objected to the proofs of claim
After carefully considering the arguments of the parties (as advanced orally and in writing both pre and post-trial), the evidence admitted at trial, and its own research of the legal issues raised, this Memorandum. Opinion contains the Court’s findings of fact and conclusions of law pursuant to Federal Rules of Bankruptcy Procedure 7052 and 9014.
1. JURISDICTION, AUTHORITY, AND VENUE
The district court of the Northern District of Texas has subject matter jurisdic
II. PRELIMINARY MATTERS
A. Factual and Computation Stipulations of the Parties
At the Court’s urging, the parties stipulated to a large number of undisputed facts, which are contained in the Joint Stipulations of Fact [ECF No. 1040] (the “Joint Stipulations”) filed December 30, 2015. While the Court will not repeat those factual stipulations verbatim in this Memorandum Opinion, it adopts them as if they were set forth herein.
In addition, the parties were able to stipulate to the facts that will be necessary for them to compute the amount of tax, interest, and penalties that may result from this Court’s determination of the factual and legal issues in dispute among them, which are included in the parties’ Computation Stipulations [ECF No. 1106] (the “Computation Stipulations”) filed January 26, 2016. The Computation Stipulations, like everything else in the Cases, is complicated and detailed, so suffice it to say that the Court is not going to repeat those stipulations here, but it adopts them as if they were set forth herein.
B. Facts Found Due to this Court’s Application of Collateral Estop-pel
On May 29, 2015 the IRS filed its Motion for Partial Summary Judgment on the Application of Collateral Estoppel to Facts and Conclusions Established in the Securities and Exchange Commission v. Sam Wyly et al. Litigation [ECF No. 611] (the “Motion for Partial Summary Judgment”), seeking this Court’s determination that certain findings of fact and conclusions of law made in connection with a civil action pending in federal district court in the Southern District of New York (the “SDNY Court”) were binding on the Debtors in connection with this Court’s resolu
For the reasons stated in its Memorandum Opinion and Order [ECF No. 789] entered on August 24, 2015, this Court granted the IRS’ Motion for Partial Summary Judgment, thereby giving collateral estoppel effect to sixty-four (64) specific facts and/or legal conclusions established in the SEC Action.
As will be explained more fully below, of particular significance here is the SDNY Court’s determination that certain of the offshore trusts at issue in the SEC Action and here are foreign grantor trusts of Sam and Charles. Because of this determination by the SDNY Court, and because this Court has given collateral estoppel effect to the SDNY Court’s determination, the Debtors and the IRS agree that there were substantial underpayments of income
The reference above is the first time that the Court has used the phrase “foreign grantor trust” in this opinion and it will use it and other related terms throughout this opinion. Of course, it is important to understand what the Court is referring to when using these terms. A foreign trust is defined in 26 U.S.C. § 7701 as “any trust other than a trust described in subparagraph (E) of paragraph (30).”
Although trusts are usually separate taxable entities, the grantor trust rules may require that a portion or all of a trust be ignored for income tax purposes. When this occurs, the grantor (or in some cases a beneficiary or trust powerholder) is deemed to own the trust assets. When the assets of a trust are deemed owned by its grantor under Sections 671 through 677 or Section 679 of the Internal Revenue Code (the Code), the trust is called a “grantor trust.”15
The “grantor trust rules” referred to above are contained in 26 U.S.C. §§ 671 through 679.
C. United States’ Motion to'Exclude the Expert Report, Opinions, and Testimony of Joshua S. Ruben-stein
The IRS filed a Motion to Exclude the Expert Opinions of Joshua S. Rubenstein [ECF No. 923] (the “Rubenstein Motion”) prior to trial. Because the Ruben-stein Motion was heard the day before trial was scheduled to commence, and because the Court did not have sufficient time to rule on the Rubenstein Motion before the Debtors called Mr. Rubenstein (“Rubenstein”) to testify at trial, the Court allowed Rubenstein to testify, sub
Rubenstein is a lawyer and partner at the firm of Katten Muchin Rosenman, LLP. The Debtors offered Rubenstein as an expert in “trust arid estate law and taxation of trusts, with specific experience and knowledge regarding these areas during the 1990s, and also as an expert regarding practices concerning the establishment and administration of foreign trusts during the 1990s.”
In the Rubenstein Motion, the IRS objected to Rubenstein’s proposed testimony on multiple grounds. First, the IRS contended that Rubenstein’s opinions would consist of statements of the law and legal analysis that would usurp this Court’s role as both fact finder arid the “one spokesman of the law.”
We turn first to the IRS’ argument that Rubenstein’s opinion consisted of impermissible recitations of the law and legal conclusions. It is all but axiomatic that the judge should be the sole source of the applicable legal standard in any case, and that expert testimony that attempts to tell the fact finder what law to apply is improper.
Much of Rubenstein’s expert opinion consisted of explanations of what Internal Revenue Code provisions and IRS regulations did or do not allow during the rele
However, not all of Rubenstein’s testimony consisted of statements that were simply impermissible legal analysis, opinions, and conclusions. In addition to giving general statements of both past and present law, Rubenstein also made statements that the law that governed offshore trusts and the tax treatment of such trusts during the relevant time period was, in the eyes of many practitioners, including him, uncertain.
The admissibility of this testimony regarding the fact of alleged uncertainty among members of the cross border trust and estate and tax bars as to how to interpret and apply the law during the relevant time period was a close call. As the Fifth Circuit has noted, “the task of separating impermissible questions which call for overbroad or legal responses from permissible questions is not a facile one.”
Evidence of legal uncertainty, except as it relates to defendant’s effort to show*361 the source of his state of mind, need not be received, at least where,- as here, the claimed uncertainty does not approach vagueness and is neither widely recognized nor related to a novel or unusual application of the law.
The Debtors have not introduced any evidence that the purported uncertainty in the law at issue here approached vagueness, a phrase that harkens back to the Fifth Circuit’s decision in U.S. v. Garber,
As explained below, knowledge that there was uncertainty regarding the proper legal characterization of the various offshore trusts at issue here can be imputed to Sam and Charles back to 1993.
■ As the IRS pointed out in its cross-examination of Rubenstein, Rubenstein offered no opinion as to (and was unaware of) whether Sam, Charles, or any Wyly advisor felt that there was any uncertainty in the applicable law during the relevant time period.
In closing out the analysis of the IRS’ first argument — that Rubenstein’s testimony consisted of impermissible legal conclusions — the Court will identify other testimony that Rubenstein gave that did not consist of impermissible legal conclusions. Although Rubenstein is a lawyer, this does not automatically mean that all of his testimony must therefore consist of statements of the law or legal conclusions. Ruben-stein is permitted to “testify as to legal matters when those matters involve questions of fact.”
Thus, we turn to the IRS’ second argument, that Rubenstein’s testimony is inadmissible because it is irrelevant and unreliable under Daubert and Federal Rule of Evidence 702. Two Supreme Court cases guide our analysis of the admissibility of expert opinion evidence on the basis of whether it is both relevant and reliable: Daubert v. Merrell Dow Pharm., Inc.
Nevertheless, the basic holding of Daubert, as expanded upon by Kumho Tire Co., Ltd., is very simple — in order to be admissible, expert testimony must be both (i) relevant, and (ii) reliable.
We conclude that Daubert’s general holding — setting forth the trial judge’s general “gatekeeping” obligation — applies not only to testimony based on “scientific” knowledge, but also to testimony based on “technical” and “other specialized” knowledge. See Fed. Rule Evid. 702. We also conclude that a trial court may consider one or more of the more specific factors that Daubert mentioned when doing so will help determine that testimony’s reliability. But, as the Court stated in Daubert, the test of reliability is “flexible,” and Daubert’s list of specific factors neither necessarily nor exclusively applies to all experts or in every case. Rather, the law grants a district court the same broad latitude when it decides how to determine reliability as it enjoys in respect to its ultimate reliability determination. See General Electric Co. v. Joiner,522 U.S. 136 , 143,118 S.Ct 512 ,139 L.Ed.2d 508 (1997) (courts of appeals are to apply “abuse of discretion” standard when reviewing district court’s reliability determination).
As indicated by the Supreme Court in Kumko Tire Co., Ltd.,
The IRS’ main argument as to why Ru-benstein’s testimony does not pass muster under Daubert is that Rubenstein did not opine on anything the Wylys did or any facts specific" to the Cases. Instead, Ru-benstein gave a general assessment of what the bar thought was normal or proper practice regarding offshore trusts during the relevant time period and opined as to areas where the bar thought that the law was uncertain. At the outset, the Court notes that the language of Federal Rule of Evidence 702(d) requiring an expert to apply their principles and methods “to the facts of the case” does not per se exclude expert testimony that does not refer to the facts of the particular case before the fact finder.
Despite these concerns, Rubenstein’s testimony that, during the relevant time periods: (i) the use of protectors in the context of foreign trusts was permissible and even common, (ii) de facto control of trustees by grantors was not out of the ordinary, and (iii) the use of “accommodation grantors” was thought to be legitimate is admittedly of some relevance here. It is helpful for the Court to understand that these practices — in and of themselves— were not considered to be inappropriate by the cross-border trust and estate and tax bars during the relevant time period.
Despite its limited relevance, Ruben-stein’s opinions are reliable for what they are as shown by his curriculum vitae (CV), testimony at the Daubert hearing, and testimony at trial — his recollections based on his experience as an admittedly prominent and accomplished cross-border trust and estate and tax lawyer who practiced during the relevant time period, coupled with some confirmatory research.
As the Supreme Court counseled in Daubert,
Finally, we address the IRS’ third argument — that Rubenstein was not qualified to give an opinion on the private annuity transactions at issue here. The IRS argued that Rubenstein’s lack of experience with private annuity transactions in a foreign trust context rendered him unqualified under Federal Rule of Evidence 702 to give any opinion related to the private annuity transactions at issue here.
Rubenstein is an experienced cross-border trust and estate and tax lawyer, as his CV amply demonstrates.
Dee filed a Motion for Partial Summary Judgment [ECF No. 879] on November 16, 2015, seeking to have this Court determine that there was no evidence in the record to support the IRS’ claim for fraud penalties under 26 U.S.C. § 6663. The IRS opposed Dee’s motion, which motion was heard on December 21, 2015, shortly before trial was scheduled to commence. Given (i) other more pressing matters in preparing for trial, and (ii) the timing of when the parties filed briefs on Dee’s innocent spouse defense, which the Court wanted to read and understand before ruling on her motion for partial summary judgment, the Court simply ran out of time to rule on her motion before trial. The motion is now moot, as the issues were fully tried by the parties.
III. FACTUAL AND PROCEDURAL HISTORY
While the parties stipulated to many facts as noted previously, the Court will briefly summarize certain facts in order to put its legal analysis into context. This summary is, by definition, incomplete, and more facts will be found and analyzed throughout this Memorandum Opinion.
As noted previously, Sam and Charles are brothers who grew up in modest circumstances in northeast Louisiana. Charles was about a year older than Sam and they were close friends and business associates throughout their adult lives. As relevant here, Sam founded his first company, University Computing Company in 1963.
Sam was the Chairman of the Executive Committee and a Director of Sterling Commerce, Inc. (“Sterling Commerce”) from December 1995 through its acquisition by SBC Communications in 2000.
Sam was the Chairman of the Board of Michaels Stores, Inc. (“Michaels Stores”) from 1984 through July 2001 and Vice-Chairman of the Board from July 2001 through its acquisition by a consortium of private equity firms in 2006.
Charles was a co-founder of Sterling Software and served as its Vice-Chairman of the Board from 1984 through its acquisition by Computer Associates in 2000.
Given the wide variety of business ventures Sam and Charles were involved in, they needed administrative help. Sharyl Robertson (“Robertson”) started working for the Wylys as a bookkeeper in the late 1970s and eventually became chief financial officer of Highland Stargate, Ltd., a Texas Limited Partnership, which is the Wyly family office located in Dallas (“Highland Stargate” or “Wyly family office”).
Keeley Hennington (“Hennington”) began working for Highland Stargate in January 1999 as tax director.
Given the wide variety of business ventures the Wylys were involved in, they also needed legal help. Michael French (“French”) is an attorney licensed to practice law in Texas.
French testified that he left Jackson Walker to become a consultant to two Wyly-related entities — Sterling Software and Michaels Stores.
When Jeannette Meier, the general counsel of Sterling Software, expressed a preference for Jones Day as an outside law firm, French also became a “consultant” to Jones Day from 1995 through 2000, after which Jones Day started doing work for Sterling Software and Michaels Stores.
Starting in 1995, French officed with the Wylys at the Wyly family office. From 1993 to 2000, the Wylys decided the amount of French’s total compensation paid by entities controlled by or affiliated with them.
Dee is Charles’ widow, having met and married him during college at Louisiana Tech.
By 1990, Sam and Charles had accumulated enormous wealth. , As the SDNY Court found, and was independently established here, “in early to mid-1991, .Sam Wyly asked Robertson to attend a seminar held by lawyer and trust promoter David Tedder [“Tedder”] on the use of foreign trusts as a method of asset protection and tax deferral.”
1. Never pay probate unless there is a tax advantage in your state (not in Texas).
2. Whenever possible eliminate inheritance tax — Tedder says everyone can reduce it to zero.
3. Wherever possible reduce income tax — both domestically and foreign.
4. Never let a creditor get your asset, no matter how bad your mistake. (In 18 years of practice, Tedder’s firm has never had a creditor successfully pierce the asset protection setup).[109 ]
5. Be able to change your asset protection/tax savings system.
6. Feel comfortable with the setup you’ve got. If your [sic] not comfortable with a foreign setup don’t do it.
The Tedder Seminar Memo further identified “[t]he three major sources of creditor problems — unknown creditor, IRS-inheritance, IRS-income tax.”
The Tedder Seminar Memo also warned to “-[ajlways show your chart to the creditor, rely on law not secrecy.”
Sam was interested in the programs outlined in the Tedder Seminar Memo and related documents. Thus, as found by the SDNY Court, and independently established here, “[s]hortly thereafter, the Wy-lys, Robertson, and French attended another Tedder seminar in New Orleans.”
Specifically, in Malibu, Tedder told the Wylys that they could establish offshore trusts in the Isle of Man (“IOM”) and transfer their stock options in Michaels Stores and Sterling Software to those trusts in exchange for annuities.
In part because of the complexity of the record keeping required to support the Wyly offshore system, and in part because of their desire for secrecy and to make access to the records of the offshore system more difficult for their creditors, including the IRS, to obtain if there was ever a challenge to the offshore system, Sam and Charles implemented an offshore version of their Dallas family office in the mid-1990s called Irish Trust Company (“Irish Trust”), an entity domiciled in the Cayman Islands and indirectly owned by two of the Wyly IOM trusts.
Michelle Boucher (“Boucher”) became a trusted Wyly advisor in approximately 1995 and then became a protector of the Wyly IOM trusts in 2001.
Prior to becoming a trust protector herself, Boucher served as a conduit, the person who communicated the Wylys’ recommendations between the protectors (Robertson and French) and the various IOM trustees.
We were already aware of the roles played by Michael French and Sharyl Robertson, representing Maverick Capital and the Wyly Family, and firstly the role of Michelle Boucher was explained .... We will therefore have ;prime contact with Michelle in most situations as she is to act as the focus of communications and maintain records etc. which should not be seen in the USA_Michael and Sharyl are anxious that any trail of communications between themselves, Michelle and Mees-Pierson does not give rise to any potential claim that control is being exercised-in the USA Consequently we may anticipate that there will be telephone communications only from Dallas; suggestions possibly put forward via Michelle Boucher but it was agreed that there should be formal recommendations made by the Trustees to the Protectors Committee wherever appropriate to maintain a required direction of control.
After a chance meeting in the Cayman Islands in mid-2003 between Charles Lu-bar (“Lubar”), a prominent international tax attorney, and Boucher, Boucher learned that Lubar (i) had previously concluded that there was a “significant risk” that the 1992 IOM trusts settled by Sam and Charles would be treated as grantor trusts to them under the Internal Revenue Code, and (ii) had informed French of his firm’s conclusions a decade earlier.
First, Hennington and Boucher met with Lubar at his London office where Lubar’s concerns with the offshore system dating back to 1993 were discussed in detail. Hennington and Boucher informed Sam and Charles, among others, of Lubar’s legal conclusions.
Second, acting as agents for Sam and Charles, Hennington and Boucher hired Lubar to reanalyze all of the issues surrounding the Wyly offshore system, which he did and which confirmed his original conclusions. Lubar ultimately recommended an anonymous meeting with the IRS on the Wylys’ behalf to see if a global resolution of the tax issues surrounding the Wyly offshore system could be achieved, which recommendation the Wy-
Third, because the extended due date of Sam’s 2002 tax return was quickly approaching (October 15, 20Ó3), and given that Meadows Owens had been advising the Wylys for years and had apparently given advice to them previously about the offshore system,
Early in 2004, the IRS commenced an audit of the Wylys’ returns for the 2000 tax year. From the beginning of the audit it was clear that the IRS was examining the offshore trusts and the annuity transaction undertaken offshore.
The Permanent Subcommittee on Investigations of the United States Senate'undertook an investigation of tax haven abuses. The Wylys offshore system was one of the offshore systems investigated. That investigation became public knowledge
By April of 2005, Bickel & Brewer and Donald Lan
On July 30, 2010, the SEC sued Sam, Charles, and French, among others, in the SEC Action, asserting ten counts of securities fraud. French settled with the SEC.
On October 19, 2014, shortly before judgment was entered against him in the SEC Action, Sam filed his Case here. Shortly thereafter, Dee filed her Case here. The Cases are being jointly administered. On the day each Case was filed, the Debtor’s respective Motion was filed. The ÍRS timely filed the Proofs of Claim against each of the Debtors and the Debtors filed the Claim Objections, which brings us to the present dispute before the Court.
IV. LEGAL ANALYSIS
A. Burden of Proof
Like most aspects of the Cases, the burden of proof analysis is complicated. The fact that the IRS is asserting federal tax liability in the context of the Proofs of Claim implicates not only the burden-shifting analysis applicable to proofs of claim in bankruptcy generally, but also multiple additional burden shifting doctrines and statutory allocations of burdens of proof that apply specifically to tax matters. None of these burden of proof analyses are exactly alike, so the Court will proceed in the only way it can — by analyzing each burden of proof framework before coming to its ultimate conclusions.
1. Bankruptcy Law Burden of Proof — In General
In bankruptcy, a proof of claim filed in accordance with Bankruptcy Rule
The Debtors’ arguments here regarding burden of proof implicate every step of the bankruptcy burden of proof analysis, to which we now turn.
a) Prima Facie Validity under Bankruptcy Rule 3001(f)
The Debtors initially argue that the burden of proof lies with the IRS because the Proofs of Claim were not filed in accordance with Bankruptcy Rule 3001, and thus do not constitute prima facie evidence of the validity or amount of the IRS’ claims.
Although much of the “fuss” surrounding the burden of proof issues revolved around the now-stipulated income tax liability amounts reflected in the Computation Stipulations, the Court undertakes the
Regarding the failure of the IRS to attach an itemized statement of the interest, fees, expenses, or charges to the Proofs of Claim,- it must first be noted that such failure was not complete. In the Proofs of Claim filed by the IRS in these Cases, the IRS did break out the amount of income tax due and interest on income tax due on a year-by-year basis, as well as the amount of gift tax due and interest on gift tax due on a year-by-year basis.
Bankruptcy Rule 3001(c)(2)(D) provides the appropriate remedies that a court may invoke for a creditor’s failure to attach the itemized statement required by Bankruptcy Rule 3001(c)(2)(A). These remedies include precluding the IRS from presenting the omitted information (unless the Court determines that the IRS’ failure to include this information “was substantially justified or is' harmless”
In light of the highly, unique facts of these Cases, the Court does not choose to exercise either of these (or any other) remedies. These Cases involved a great deal of back-and-forth between the parties, as is to be expected when billions-of dollars of potential tax liability hang in the balance.
The Advisory Committee Notes that accompany Bankruptcy Rule 3001 state that subsection (c)(2) was added:
to require additional information to accompany proofs of claim filed in cases in which the debtor is an individual. When the holder of a claim seeks to recover-in addition to the principal amount of a debt-interest, fees, expenses, or other charges, the proof of claim must be accompanied by a .statement itemizing these additional amounts with sufficient specificity to make clear the basis for the claimed amount.167
Even though the IRS did not attach a completely itemized statement as required by Bankruptcy Rule 3001(c)(2)(A), it did “make clear the basis for the claimed amount” to the Debtors through the itemized statement that was attached to its Proofs of Claim, its presentation to the Debtors, and through regular communication with Debtors’ counsel. The IRS did not act as a recalcitrant creditor who refused to provide information to the Debtors. On the contrary, the evidence shows that the IRS was very forthcoming with information about how it calculated its claims, and because of this, at least in part, the parties were able to come to the Computation Stipulations.
In light of the fact that the Debtors were supplied with a great deal of information regarding the amounts of interest and penalties asserted in the Proofs of Claim, the IRS’ failure to supply a fully itemized statement of interest, fees, expenses, or other charges as required by Bankruptcy Rule 3001(c)(2)(A) was harmless, and did not affect the Proofs of Claim’s prima facie validity.
The Debtors also argue that the Proofs of Claim are not prima facie valid because the IRS insolvency specialist who signed them relied on other IRS staff to prepare them and simply accepted their calculations as true and accurate without checking them.
Finally, the Debtors argue that the Proofs of Claim are deficient because “[t]he IRS Claims lack any explanation as to the basic facts on which the IRS relies to determine the alleged liabilities; instead the IRS Claims contain only bare-bones legal conclusions without reference to any facts whatsoever.”
When all is said and done, the Proofs of Claim fulfilled their “essential purpose of providing objecting parties with sufficient information to evaluate the nature of the claims.”
b) Have the Debtors Raised Evidence of a Probative Force Equal to that of the Proofs of Claim?
The Debtors next argue that even if the Proofs of Claim are afforded prima facie validity, they have raised evidence of a probative force equal to that of the Proofs of Claim.
The Debtors imply that they could raise evidence of equal probative force to the Proofs of Claim merely by stating that the IRS’ claimed amounts are “too high.”
Accordingly, we must further examine what sort of evidence could meet the standard of “equal in probative force” and whether the Debtors raised such evi-, dence here. As this Court recently held, once the prima facie validity of a proof of claim under Bankruptcy Rule 3001(f) is established:
The burden of going forward with the evidence then shifts to the objecting party to produce evidence at least equal in probative force to that offered by the proof of claim and which,' if believed, would refute at least one of the allegations that is essential to the claim’s legal sufficiency. This can be done by the objecting party producing specific and detailed allegations that place the claim into dispute, by the presentation of legal arguments based upon .the contents of the claim and its supporting documents, or by the presentation of pretrial pleadings, such as a motion for summary judgment, in which evidence is presented to bring the validity of the claim into question.181
Here, the Proofs of Claim seek amounts from the Debtors that fall into four basic categories: (i) income taxes, (ii) gift taxes, (iii) fraud penalties, and (iv) failure to file penalties.
However, a dispute remains regarding whether any gifts were actually made by the Debtors, for which the IRS is asserting gift taxes (and associated penalties). The Debtors have raised legal arguments that create doubts as to whether gifts were made. The Debtors also introduced evidence suggesting that the transactions that remain at issue were not gifts.
The parties likewise agree — as does this Court — that the IRS bears the burden of proving its claim for fraud penalties (for both income and gift tax underpayments) by clear and convincing evidence.
Regarding the IRS’ claims for international failure to file penalties, the Debtors also raised legal arguments that cast into doubt at least some of the IRS’ assertions that the Debtors failed to file certain required forms.
2. Tax Law Burden of Proof — In General
As noted previously, in 2000, the Supreme Court held that “bankruptcy does not alter the burden imposed by the substantive law.”
a) Gift Tax Deficiencies and the Presumption of Correctness
The burden of proof analy-ses — there are two relevant here — regarding gift tax deficiencies are by far the most complicated of the tax law burden of proof analyses that this Court must address. However, before reaching those analyses we must discuss one of the general rules regarding burden of proof in tax matters— ie., the presumption of correctness. In tax court proceedings, after the IRS has made a determination that a certain amount of tax is due, the burden of proof is usually on the taxpayer to show that the IRS’ determination is incorrect. As the Supreme Court has stated, “[unquestionably the burden of proof is on the taxpayer to show that the Commissioner’s determination is invalid.”
Fifth Circuit precedent supports the view that a proof of claim filed by the IRS should be afforded the presumption of correctness. In Portillo v. C.I.R.,
Data Industries makes two contentions in its effort to overturn the District Court’s order. First, Data contends that, notwithstanding the prima facie correctness of a claim filed in bankruptcy proceedings, the presumptive correctness arising from the underlying tax assessment cannot be invoked unless the Government produces additional evidence such as a copy of the assessment certificate. This contention simply has no merit, particularly since all pertinent information relating to the IRS assessment was contained in the proofs of claim filed by the Government in the bankruptcy proceedings.
Under this precedent, the Proofs of Claim are entitled to the presumption of correctness,
(1) Is the IRS’ Determination “Arbitrary and Erroneous?”
The Debtors first argue that the presumption of correctness should not apply because the IRS’ determinations of gift tax deficiencies are arbitrary and erroneous.
A bankruptcy court adjudicating a tax claim by the IRS must apply the burden-of-proof rubric normally applied under tax law. In an action to collect taxes, the government bears the initial burden of proof. That burden is satisfied by the IRS’ deficiency determinations and assessments for unpaid taxes, which are presumed correct so long as they are supported by a minimal factual foundation. However, a showing by the taxpayer that a determination is arbitrary, excessive or without foundation shifts the burden of proof back to the IRS. Thus, once the debtor rebuts the presumption, the burden reverts to the IRS to show that its determination was correct.
Although Olshan states that the burden will be shifted to the IRS when its deter-
Portillo v. C.I.R.
These Cases do not present a situation where the IRS’ claim for gift taxes is arbitrary and erroneous by virtue of having absolutely no evidentiary foundation.
For these reasons, the Court finds that the Proofs of Claim were not arbitrary and erroneous. ■
(2) Burden Shifting under 26 U.S.C. § 7491
The Internal Revenue Code provides one more opportunity for the Debtors to shift the burden to prove gift tax deficiencies to the IRS — ie„ 26 U.S.C. § 7491. An analysis under § 7491 focuses on the taxpayer’s actions and asks if the taxpayer has submitted credible evidence and demonstrated “good behavior” by comporting with certain statutory requirements. Specifically, 26 U.S.C. § 7491 provides as follows:
(a) Burden shifts where taxpayer produces credible evidence.—
(1) General rule. — If, in any court proceeding, a taxpayer introduces credible evidence with respect to any factual issue relevant to ascertaining the liability of the taxpayer for any tax imposed by subtitle A or B, the Secretary shall have the burden of proof with respect to such issue.
(2) Limitations. — Paragraph (1) shall apply with respect to an issue only if—
(A) the taxpayer has complied with the requirements under this title to substantiate any item;
(B) the taxpayer has maintained all records required under this title and has cooperated with reasonable requests by the Secretary for witnesses, information, documents, meetings, and interviews; and
*[■ H*
(3) Coordination. — Paragraph (1) shall not apply to any issue if any other provision of this title provides for a specific burden of proof with respect to such issue.
* # %
(c) Penalties. — Notwithstanding any other provision of this title, the Secretary shall have the burden of production in any court proceeding with respect to the liability of any individual for any penalty, addition to tax, or additional amount imposed by this title.
As explained by the district court in Southgate Master Fund, LLC,211
The legislative history of Section 7491 defines “credible evidence” as “the quality of evidence which, after critical analysis, the court would find sufficient upon which to base a decision on the issue if no contrary evidence were submitted*384 (without regard to the judicial presumption of IRS correctness).” S.Rep. No. 105-174,1998 WL 197371 , at *45. Additionally, “[a] taxpayer has not produced credible evidence for these purposes if the taxpayer merely makes implausible factual assertions, frivolous claims, or tax protestor-type arguments. The introduction of evidence will not meet this standard if the court is not convinced that it is worthy of belief.” Id. at *45-46.
This is not a case where either side has raised implausible factual assertions, frivolous claims, or tax protestor-type arguments. Rather, the Court finds, based on the evidence discussed more thoroughly in other sections of this opinion,
As this is not a case involving deductions, losses, or credits, the substantiation requirement of § 7491(a)(2)(A) seems to meld into the record keeping requirement of § 7491(a)(2)(B). The legislative history of § 7491 confirms this:
Nothing in the provision shall be construed to override any requirement under the Code or regulations to substantiate any item. Accordingly, taxpayers must meet applicable substantiation requirements, whether generally imposed or imposed with respect to specific items, such as charitable contributions or meals, entertainment, travel, and certain other expenses. Substantiation requirements include any requirement of the Code or regulations that the taxpayer establish an item to the satisfaction'of the Secretary. Taxpayers who fail to substantiate any item in accordance with the legal requirement of substantiation will not have satisfied the legal conditions that are prerequisite to claiming the item on the taxpayer’s tax return and will accordingly be unable to avail themselves of this provision regarding the burden of proof. Thus, if a taxpayer required to substantiate an item fails to do so in the manner required (or destroys the substantiation), this burden of proof provision is inapplicable.
The legislative history of § 7491 in turn cites to 26 U.S.C. §§ 6001, 6038, and 6038A as examples of “generally imposed” substantiation requirements. Section 6001 states, in part, that “[e]very person liable for any tax imposed by this title, or for the collection thereof, shall keep such records, render such statements, make such returns, and comply with such rules and regulations as the Secretary may from time to time prescribe.” Likewise, §§ 6038 and 6038A require taxpayers to file information regarding certain foreign-owned corporations and partnerships. Thus, the very examples that Congress gives of “substantiation” requirements are in actuality requirements to keep records. With this in mind, these substantiation requirements will be analyzed under the framework of § 7491(a)(2)(B)’s record keeping requirement.
Under § 7491(a)(2)(B), the taxpayer must maintain all required records to qualify for a shift in the burden of proof to the IRS. The Motions and Claim Ob
Under § 7491(a)(2)(B) taxpayers must also cooperate with reasonable requests by the Secretary for witnesses, information, documents, meetings, and interviews in order to qualify for a shift in the burden of proof. The legislative history of § 7491 explains the cooperation requirement in this way:
the taxpayer must cooperate with reasonable requests by the Secretary for meetings, interviews, witnesses, information, and documents (including providing, within a reasonable period of time, access to and inspection of witnesses, information, and documents within the control of the taxpayer, as reasonably requested by the Secretary). Cooperation also includes providing reasonable assistance to the Secretary in obtaining access to and inspection of witnesses, information, or documents not within the control of the taxpayer (including any witnesses, information, or documents located in foreign countries).
Although it is true that the Wylys exercised their rights during the audit process, they did not refuse to meet with IRS agents and worked diligently to respond to information document requests (“IDRs”) submitted to them by the IRS.
For these reasons, the Court is satisfied that the Debtors have met their burden under 26 U.S.C. § 7491. Thus, at the end of a long journey through multiple burden of proof analyses, the burden lies with the IRS to prove the Debtors’ liability for gift
b) Fraud Penalties for Income Tax and Gift Tax Underpayments
The burden of proof analysis regarding fraud is much more straightforward than the gift tax analyses. The statutes and procedural rules governing practice before the tax court make it clear that the IRS bears the burden of proving fraud by clear and convincing evidence.
That the IRS bears the burden of establishing a taxpayer’s fraud by clear and convincing evidence seems to be universally understood, and statements to this effect are found in both tax court cases and Circuit level cases outside of the Fifth Circuit.
Moreover, courts agree that the IRS must carry its burden of establishing fraud by clear and convincing evidence separately for each tax year at issue.
26 U.S.C. § 6663 — the statute mandating penalties for fraudulent underpayment of taxes — itself also contains instructions to follow regarding burdens of proof, and states in subsection (b) that “[i]f the Secretary establishes that any portion of an underpayment is attributable to fraud, the entire underpayment shall be treated as attributable to fraud, except with inspect to any portion of the underpayment which the taxpayer establishes (by a preponderance of the evidence) is not attributable to fraud.”
As relevant here then, the burden of proof regarding its claims for fraud penalties pursuant to 26 U.S.C. §§ 6663 and 6651 is on the IRS, who must carry that burden by clear and convincing evidence. Of course, and as the parties agree, if the IRS carries its burden of proof, the statute of limitations under 26 U.S.C. § 6501(c)(1) remains open for each year in which the IRS proves the return was fraudulent.
c) International Failure to File Penalties
Again, the burden of proof analysis regarding international failure to file penalties is straightforward. 26 U.S.C. § 7491(c) provides that:
Notwithstanding any other provision of this title, the Secretary shall have the burden of production in any court proceeding with respect to the liability of any individual for any penalty, addition to tax, or additional amount imposed by this title.
3i The Debtors’ Defenses
The Debtors assert various defenses to their liability to the IRS. Each is discussed below.
a) Reasonable Cause Defenses
The Debtors assert multiple reasonable cause defenses under multiple sections of the Internal Revenue Code. These reasonable cause defenses, if proven by the Debtors, will allow them to avoid liability for various penalties asserted by the IRS in the Proofs of Claim. First, the Debtors assert a reasonable cause defense to the IRS’ assertion of fraud penalties under 26 U.S.C. § 6664(c).
All of these reasonable cause defenses would negate a taxpayer’s liability upon similar showings of a combination of “reasonable cause,” “good faith,” and a “lack of willful neglect.” Absent contrary guidance from Congress (and there is no such contrary guidance here), it makes sense to assume that these phrases have the same meaning throughout the Internal Revenue Code.
Dee’s “innocent spouse defense” is codified at 26 U.S.C. § 6015. It provides an exception to the general rule of federal income taxation that a husband and wife filing a joint return are jointly and severally liable for the taxes due on that return.
Dee claims that she is eligible for innocent spouse relief under §§ 6015(b) and (c), but not § 6015(f). As relevant here, Dee bears the burden of proof on the innocent spouse defense:
Except for the knowledge requirement of § 6015(c)(8)(C) (the provision disallowing election of separate liability to a spouse with actual knowledge of the item giving rise to the deficiency), the taxpayer bears the burden of proving that she has met all the prerequisites for innocent spouse relief. See Reser v. Comm’r,112 F.3d 1258 , 1262-63 (5th Cir.1997). Section 6015(c)(3)(C) explicitly places the burden of proof on the Secretary.242
Dee must satisfy her burden here by a preponderance of the evidence.
Armed with this understanding of the applicable burdens of proof, we turn to the substantive issues we must address.
B. Was the Debtors’ Underpayment of Income Taxes Due to Fraudulent Intent?
As noted previously, to prevail here on its claim for fraud penalties under 26. U.S.C. § 6663, the IRS must prove, by clear and convincing evidence for each tax year in question, that: (i) the Debtors underpaid their respective income tax that year,
From Sam’s perspective, he is the embodiment of the American dream — small town boy of modest background makes good through, among other things, a close family, hard work, intelligence, business savvy, some good ideas, and a willingness to take entrepreneurial risks, which combine to transform him into one of the wealthiest individuals in the world. This spin on the tale at trial started with a lengthy tracing of Sam’s and Charles’ childhood in small towns in northeastern Louisiana, through their teenage years as Boy Scouts (including a recitation of the Boy Scout oath) and student athletes (according to Sam, he was the better student and Charles was the better athlete), to college at Louisiana Tech where Charles met and ultimately married Dee, his wife of 56 years before his death in 2011, to Sam’s graduate school at the University of Michigan on scholarship, to Sam’s first job at IBM where he met his friend Ross Perot, who was just starting out in the business world like he was, to the start of Charles and his first business venture, and so on. The upshot of Sam’s story is that he is a loyal American, who loves his family
Conversely, while the IRS does not dispute the impressive rags to riches story of Sam and Charles, or the impressive nature of their overall business successes, it spins its own tale of two brothers, who are extraordinarily wealthy by the early 1990s and who decide to evade taxes in order to
This Court’s job is to take the parties’ respective stories, of which there is certainly evidence of support in the record, and decide which version of the facts or, in all likelihood, combination of versions of the facts, is most credible and reflects what happened here (by clear and convincing evidence if the IRS is to prevail on their fraud penalty claims). To say this has been a difficult process of weighing the conflicting evidence and arguments is a great understatement. The Court’s analysis of the fraud penalties issue — as it relates to the Debtors’ income tax underpayments — follows.
As virtually every case addressing fraud penalties pursuant to 26 U.S.C. § 6663 acknowledges, a taxpayer rarely confesses his or her fraud in what the parties here have called a Perry Mason moment.
1. Relevant Statutes and Badges of Fraud
With this general statement of the law in mind, the Court begins by analyzing the relevant statutes and the badges of fraud it believes applicable here. 26 U.S.C. § 6663 provides:
(a)Imposition of penalty. — If any part of any underpayment of tax required to be shown on a return is due to fraud, there shall be added to the tax an amount equal to 75 percent of the portion of the underpayment which is attributable to fraud.
(b) Determination of portion attributable to fraud. — If the Secretary establishes that any portion of an underpayment is attributable to fraud, the entire underpayment shall be treated as attributable to fraud, except with respect to any portion of the underpayment which the taxpayer establishes (by a preponderance of the evidence) is not attributable to fraud.
(c) Special rule for joint returns. — In the case of a joint return, this section shall not apply with respect to a spouse unless some part of the underpayment is due to the fraud of such spouse.
In turn, 26 U.S.C. § 6664 provides, in relevant part, that;
(b) Penalties applicable only where return filed. — The penalties provided in this part shall apply only in cases where a return of tax is filed (other than a return prepared by the Secretary under the authority of section 6020(b)).
(c) Reasonable cause exception for underpayments.—
*393 (1) In general. — No penalty shall be imposed under section 6662 or 6663 with respect to any portion of an underpayment if it is shown that there was a reasonable cause for such portion and that the taxpayer acted in good faith with respect to such portion.
(2) Exception. — Paragraph (1) shall not apply to any portion of an underpayment which is attributable to one or more transactions described in section 6662(b)(6).257
And, while the Debtors assert a reasonable cause and good faith defense to the imposition of fraud penalties for their income tax underpayments (and which will be discussed infra at pp. 476-513), their initial argument is a bit more nuanced. In short, the Debtors argue that we do not need to get to their reasonable cause and good faith defense as to their income tax underpayments, as the IRS has failed to prove fraudulent intent by clear and convincing evidence, as it is required by law to do. And, the nuance comes by virtue of the Debtors’ argument that their reliance on the advice of their various professionals in preparing and filing their tax returns in each of the relevant years negates any possible fraudulent intent. In other words, according to the Debtors, we received all this advice from all these professionals who said what we are doing was appropriate, so how could we have possibly avoided payment of a tax we believed we owed?
It bears repeating that the lists of badges of fraud relied upon by courts is described as a non-exclusive list, clearly indicating that the courts have flexibility to analyze the particular facts and circumstances of their cases and to supplement the “typical” or “usual” badges of fraud with ones that may be unique to the facts of any specific case.
The. more “usual” badges of fraud that the Court will analyze include:
a) The Complexity of the Offshore System
The offshore system of trusts and corporations set up by Sam and Charles starting in 1992 is enormously complex. In summary, Sam and/or Charles established 16 offshore trusts and 38 offshore corporations, each of which was owned by one of the 16 offshore trusts. The offshore trusts were all settled in the IOM, which is an
With this general background of the offshore system in mind, we turn to the specifics of each brother’s offshore system. On March 11, 1992, Sam settled the Bulldog Non-Grantor Trust (“Bulldog IOM Trust”) in the IOM.
IOM Corporations Date Established
Morehouse Limited March 24,1992
West Carroll Limited March 24,1992
Tensas Limited March 24,1992
Richland Limited March 24,1992
East Carroll Limited March 24,1992
East Baton Rouge Limited March 27,1992
Moberly Limited January 31,1996
Locke Limited February 8,1996
On December 4, 1992, Sam settled the Lake Providence International Trust (“Lake Providence IOM Trust”) in the IOM.
On December 14, 1992, Sam settled the Delhi International Trust (“Delhi IOM Trust”) 4n the IOM.
On February 2, 1994, Keith King (“King”), a resident of the IOM, settled the Bessie Trust (“Bessie IOM Trust”) in the IOM.
IOM Corporations Date Established
Yurta Faf Limited (IOM) June 28,1994
Audubon Asset Limited (f/k/a Fugue Limited) (“Audubon Asset Limited (IOM)”) October 18,1995
Newgale Limited (IOM) March 12,2003
Cayman Exempted Corporations Date Established
Orange L.L.C. (Cayman) June 1,2001
FloFlo L.L.C. (Cayman) June 1,2001
Bubba L.L.C. (Cayman) June 1,2001
Pops L.L.C. (Cayman) June 1,2001
Balch L.L.C. (Cayman) June 1,2001
Katy L.L.C. (Cayman) June 1,2001
The Cayman Exempted Corporations listed above were liquidated in 2006 and ownership of their assets reverted 100% to the Bessie IOM Trust (to the extent there remained any assets after the payment of liabilities).
Mi Casa Limited, an IOM corporation (“Mi Casa Limited (IOM)”), established on March 28, 2001, was initially wholly owned by the Bessie IOM Trust. Mi Casa Limited (IOM) was later owned by FloFÍo L.L.C. (Cayman) and the Bessie IOM Trust.
Cottonwood I Limited, an IOM corporation (“Cottonwood I Limited (IOM)”), established on July 14, 2000, was initially wholly owned by the Bessie IOM Trust. As of June 1, 2002, Cottonwood I Limited (IOM) was owned by Bubba L.L.C. (Cayman) and Bessie IOM Trust.
Cottonwood II Limited, an IOM corporation (“Cottonwood II Limited (IOM)”),
Spitting Lion Limited, an IOM corporation (“Spitting Lion Limited (IOM)”), established on February 3, 2000, was initially wholly owed by the Bessie IOM Trust.
Woody Creek Ranch Limited, an IOM corporation formed on September 30, 1999 (whose name was changed to Two Mile Ranch Limited on April 14, 2000, and ultimately to Rosemary’s Circle R Ranch Limited on August 26, 2003) (“Rosemary’s Circle R Ranch Limited (IOM)”), was initially wholly owned by Devotion Limited (IOM), another Sam IOM corporation discussed further below.
On July 18, 1995, the La Fourche Trust (“La Fourche IOM Trust”) was settled in the IOM by Shaun Cairns (“Cairns”), an IOM resident.
On March 11, 1992, Sam settled the Tallulah International Trust (“Tallulah IOM Trust”) in the IOM with $100.00.
On December 21, 1995, Sam settled The Crazy Horse Trust (“Crazy Horse IOM Trust”) in the IOM with $100.00.
On December 28, 1995, Sam settled The Arlington Trust (“Arlington IOM Trust”) in the IOM with $100.00.
On January 23, 1996, Sam settled The Sitting Bull Trust (“Sitting Bull IOM Trust”) in the IOM with $100.00.
A chart depicting Sam’s overall offshore system is attached as Exhibit B.
While using fewer entities, a similarly complex offshore system was established simultaneously by Charles. Specifically, on March 23, 1992, Charles settled the Pitkin Non-Grantor Trust (“Pitkin IOM Trust”) in the IOM.
IOM Corporations Date Established
Rugosa Limited October 31,1989
Little Woody Limited March 27,1992
Roaring Fork Limited April 3,1992
Roaring Creek Limited April 3,1992
On December 4, 1992, Charles settled the Castle Creek International Trust (“Castle Creek IOM Trust”) in the IOM.
On February 2, 1994, King settled The Tyler Trust (“Tyler IOM Trust”) in the IOM.
IOM Corporations Date Established
Soulieana Limited (IOM) July 26,1995
Elysium Limited (IOM) July 10,1995
Gorsemoor Limited (IOM) January 29,1999
Little Woody Creek Road Limited OM) November 5,1999
Stargate Farms Limited (IOM) December 18,2000
On July 8, 1995, Cairns settled The Red Mountain Trust (“Red Mountain IOM Trust”) in the IOM.
On March 23, 1992, Charles settled the Woody International Trust (“Woody Int’l IOM Trust”) with $100.00 in the IOM.
On December 28, 1995, Charles settled the Maroon Creek Trust (“Maroon Creek IOM Trust”) with $100.00 in the IOM. Maroon Creek IOM Trust was a grantor trust to Charles under 26 U.S.C. §§ 671-679.
On January 23, 1996, Charles settled The Lincoln Creek Trust (“Lincoln Creek IOM Trust”) with $100.00 in the IOM. Lincoln Creek IOM Trust was a grantor trust to Charles under 26 U.S.C. §§ 671-679. Lincoln Creek IOM Trust terminated and dissolved on December 31, 1996.
A chart depicting Charles’ overall offshore structure is attached as Exhibit C.
Once the offshore system was established (or at least part of it was established), Sam and Charles undertook a series of complex annuity transactions in order to get substantial amounts of their wealth offshore in the IOM. Specifically, in 1992 and 1996, Sam and Charles entered into multiple transactions whereby they transferred securities that they had earned from Sterling Software, Sterling Commerce, and Michaels Stores in exchange for private annuities. These transactions are described in detail in Joint Stipulations ¶¶ 119-160, but two of Sam’s transactions will be summarized here for context.
For example, in 1992, Sam transferred 375,000 options to purchase stock in Mi-chaels Stores to East Baton Rouge Ltd. (Nevada), a newly formed entity that had no assets, in exchange for an unsecured private annuity.
The structure of the private annuity transactions changed in 1996,
The structure of the annuity transactions undertaken by Charles was identical to those undertaken by Sam in 1992 and 1996. Charles did four private annuity transactions in 199 2
After deferring receipt of his annuity payments,
The Wylys offered some explanation for the complexity of their offshore structures, but often those explanations only lead to an analysis of other badges of fraud. For example, Sam’s private annuity transactions in 1992 involved six Nevada corporations
Similarly complex structures were undertaken through the Bessie IOM Trust’s ownership of five IOM corporations (Mi Casa Limited (IOM), Cottonwood I Limited (IOM), Cottonwood II Limited (IOM), Rosemary’s Circle R Ranch Limited (IOM), and Spitting Lion Limited (IOM)) that were used to indirectly purchase and hold title to real estate in the United States through the five IOM corporations establishment of a domestic “management” trust, which would then establish a Texas or Colorado limited liability company depending on where the real property was located, which would hold legal title to the real property. As the IRS correctly points out, if the Bessie IOM Trust had wanted to invest in U.S. real estate, it certainly could have done so in a much simpler structure. But, the layers upon layers of entities made it that much more likely that the existence and complexity of the offshore system could remain secret from the IRS. And, through this structure, a Wyly family member or former family member could obtain a small percentage ownership interest in the management trust and then, according to Wyly family tax lawyers, enjoy the benefits of that real property, by living in a home rent free or operating a business rent free in the property. In addition to the alleged lack of economic substance to these structures, the IRS attacks them as gifts from Sam to the respective family member(s) ’ who enjoyed the use of the real property, which will be discussed further below.
Another IOM entity owned by the Bessie IOM Trust, Audubon Asset Limited (IOM),
As the above analysis demonstrates, the Wyly’s offshore system was more complex than it needed to be. There is little credible evidence in the record suggesting a legitimate business reason requiring this level of complexity. As the Court can now independently attest, attempting to understand the structure and the myriad of transactions undertaken through the structure has required days and days (if not weeks and weeks) of thoughtful analysis. With little legitimate business explanation for the complexity, the Court infers— which inference is unquestionably supported by the record — that a primary reason for making the offshore system this complex was the hope that no one, including the Court, could ever figure out what was going on here and why. This badge of fraud was established by clear and convincing evidence from 1992 through 2013 as to Sam, which are all of the tax years at issue in the Motions, and' from 1992 through 2011 as to Charles.
As this badge of fraud relates to Dee, however, the Court concludes that there is simply no evidence that Dee participated in the formation of the offshore system to any great extent, although she did sign some documents that Charles asked her to sign — albeit, without reading them. Dee testified credibly that (i) she was not involved in Charles’ business affairs, (ii) never discussed business with him, and (iii) trusted him such that when he asked her to sign a document she would, without question. The Court believes her and simply cannot imagine her even being inter
By way of background, and to give context for the above findings, Dee and Charles met and married while in college at Louisiana Tech. While Dee completed three years of college, she did not finish her degree after they married. In short, Dee was a homemaker who raised their children while Charles supported the family financially.
For these reasons this badge of fraud does not apply to Dee.
b) The Wylys’ Willingness to Commit Securities Fraud to Preserve the Secret Offshore System and to Maintain its Tax Advantages.
The SDNY Court made the following findings and conclusions, which this Court has given collateral estoppel effect to and most of which were independently established here:
Between 1992 and 1996, Sam and Charles Wyly created a number' of IOM trusts, each of which owned several subsidiary companies. Michael French, the Wylys’ family attorney, Sharyl Robertson, the Chief Financial Officer (“CFO”) of the Wyly family office, and Michelle Boucher, the CFO of the Irish Trust Company, a Wyly-related entity in the Cayman Islands, served as protectors of the IOM trusts. French, Robertson, and Boucher conveyed the Wylys’ investment recommendations to the trust management companies administering the Wylys’ IOM trusts (the “IOM trustees”). All of the IOM trustees’ securities transactions were based on the Wy-lys’ recommendations and the IOM trustees never declined to follow a Wyly recommendation.370
The Wylys served as directors of Mi-chaels Stores, Sterling Software, Sterling Commerce, and Scottish Annuity and Life Holdings, Ltd. (“Scottish Re”). As part of their compensation, the Wy-lys received stock options and warrants. “Between 1992 and 1999, Sam and Charles Wyly sold or transferred to the [IOM] trusts and companies stock options in Michaels Stores, Sterling Software and Sterling Commerce” in exchange for private annuities while simultaneously disclaiming beneficial ownership over the securities in public*409 filings with the SEC. Between 1995 and 2005, the IOM trusts and companies exercised these options and warrants, separately acquired options and stock in all four companies, and sold the shares, without filing disclosures.371 The jury found that the Wylys were beneficial owners of the Issuer securities transferred to, held, and sold by the IOM trusts because the Wylys, directly or indirectly, had or shared voting and/or investment power over these securities. Thus, the jury concluded that the Wylys failed to accurately disclose the extent of their beneficial ownership in the Issuer securities under sections 13(d) and 16(a) of the Securities Exchange Act (the “Exchange Act”). The jury also found that the Wylys caused the Issuers to violate section 14(a) of the Exchange Act, because the Wylys misrepresented the extent of their beneficial ownership to the Issuers in their Director and Officer (“D & 0”) questionnaires, which were incorporated by the Issuers in proxy statements.372
In addition to these disclosure violations, the Wylys were found liable for securities fraud in violation of section 10(b) of the Exchange Act and section 17(a) of the Securities Act of 1933 (the “Securities Act”), and for aiding and abetting the Issuers’ and the IOM trusts’ securities law violations.373
In early to mid-1991, Sam Wyly asked Robertson to attend a seminar held by lawyer and trust promoter David Ted-der on the use of foreign trusts as a method of asset protection and tax deferral. Shortly thereafter, the Wylys, Robertson, and French attended another Tedder seminar in New Orleans. Tedder, French, and the Wylys then had a private meeting at Sam Wyly’s house in Malibu, California. At that meeting, Tedder “talked about establishing trusts that would provide tax deferral, and how the Wylys could transfer assets to those trusts and get tax deferral on the growth of those assets.”374
Specifically, Tedder recommended transferring the Wylys’ stock options in Sterling Software and Michaels Stores to a foreign trust in exchange for a private annuity “in a tax-free kind of*410 transaction.” Under Tedder’s plan, it was “expressly intended that [the Wy-lys] ... irrevocably surrender the enjoyment, control, ownership, and all economic benefits attributable to the ownership of the [options] which are sold in exchange for the private annuity.”375
The Wylys pursued the offshore program primarily for its tax advantages.376 However, because Tedder suggested transferring stock options in publicly traded companies — Sterling Software and Michaels Stores — any such transaction would implicate the securities laws. French testified that he raised concerns about whether the Wylys would continue to have filing obligations as directors of Sterling Software and Michaels Stores, even after the transfers. Tedder responded that making SEC filings could threaten the Wylys’ tax benefits, because “disclosure of the offshore trusts in SEC filings may lead the IRS to discover and investigate the tax issue, and ... the IRS might use the Wylys’ SEC filings against them if the tax issue was ever litigated.”377
But Sam Wyly corroborated French’s account by testifying that Tedder told him that SEC filings ‘could trigger tax problems if you had these things on file and [were] reporting the trust shares on [Schedule] 13Ds.’ Further, it would be logical to draw an inference that the Wylys would have been concerned about taking inconsistent positions in their SEC and IRS filings when millions of dollars of tax savings were at stake.378
The jury found that the Wylys always had beneficial ownership over the options, warrants, and securities held by the IOM trusts.379
Thus, the Wylys were obligated to disclose, on the filings required by sections 13 and 16, any time they or the trusts transacted in those securities. Because beneficial ownership under the securities laws turns on having-voting and/or investment power, truthful SEC filings would have forced the Wylys to admit having some element of control over the securities held by the trusts. To the Wylys, this would mean conceding some element of control over the trustees. But the Wylys believed — rightly or wrongly — that it was critical to conceal their control of the trustees in order to maintain the tax-free status of the trusts, including income from transactions in the Issuer securities.380
*411 Footnote 91.[381 ] (Sam Wyly) (“We took steps to avoid control, and those are steps to create the appearance of avoiding control. It’s reality and it’s appearance. You want the appearance to match the reality.”) Accord PX 890 (11/3/00 email from Robertson to Evan Wyly) (“Remember that it is critical from a U.S. tax standpoint that there is no appearance that the Wyly’s [sic] are in control of the trusts or the protectors.”).382
Because the Wylys made public filings showing the transfer of options to foreign trusts, and at other times publicized their relationship to the foreign trusts, the Wylys also took affirmative steps to minimize the trusts’ SEC filings to conceal the ultimate exercise and sale of those options. For example, the Wyly family office tracked the percentage of ownership each trust management company had in a particular Issuer to avoid triggering mandatory SEC reporting. Thus, as Sam Wyly testified, not making SEC filings was logically “something that consistently went on” throughout the duration of the offshore system.383
Even when it would have been otherwise helpful to assert beneficial ownership over the stock held by the foreign trusts, such as during Sam Wyly’s proxy battle for control of Computer Associates (the acquirer of Sterling Software) in February 2002, the Wylys chose not to do it in fear of inconsistent tax positions. From these facts, it is logical to draw the inference that making misleading statements in SEC filings, or not making SEC filings at all, was part of the Wylys’ plan to maintain the appearance of separation and independence from the foreign trusts.384
*412 Footnote 95. See PX 1101 (2/26/02 email from Keeley Hennington, tax director and, starting in 2000, CFO of the Wyly family office, to Boucher, attaching Hennington’s note to Sam Wyly) (“The trusts are record owners of the shares on C[omputer] Associates]’ books. If it is represented [that] there are $2.9 shares [sic], I think it is likely CA may say we show the Wyly’s [sic] only own 1.5M options and again the difference would need to be explained.... Our friendly IRS agent is still looming around and although he has verbally agreed not to look further at any foreign entities or trusts, I would not want to give him any fresh ammunition,”).385
The Wylys ultimately hired Tedder to help establish the first group of offshore trusts and subsidiary companies in 1992 (together with the Plaquemines Trust, the “Bulldog Trusts”). These trusts were settled by Sam or Charles Wyly and had beneficiaries including the Wy-lys’ wives and children and several charitable organizations. The trust deeds permitted the protectors to “add[] or substituye]” a charitable organization “by notice in writing to the trustees.” These trusts were explicitly set up as “non-grantor trust[s] rather than [ ] grantor trust[s] under Section 671-678 of the Code.” Under the terms of the trusts, no United States beneficiary could receive a distribution from the trust until two years after the settlor’s death.386
Footnote 97. (Robertson). The 1992 Trusts relevant to the remedies phase are: 1) the Bulldog Non-Grantor Trust; 2) Lake Providence International Trust; 3) the Delhi International Trust; 4) the Pitkin Non-Grantor Trust; and 5) the Castle Creek International Trust. In 1995, the Bulldog Trust settled the Plaquemines Trust, which had a class of beneficiaries including Sam Wyly’s children. These trusts are referred to as the “Bulldog Trusts” for purposes of this Opinion and Order. The terminology was coined by defendants’ expert, Professor Robert Danforth, and has been adopted by the parties in their briefing and argument,387
As the above findings and conclusions make clear, and the record here independently establishes, Sam and Charles went to great lengths, using elaborate webs of entities, to avoid accurately and completely reporting the extent of their offshore holdings and the securities transactions that were occurring offshore at their direction. As found by the SDNY Court, and as independently established here, the offshore program was pursued primarily for its tax advantages.
These facts support the existence of a badge of fraud by clear and convincing evidence as to Sam and Charles from the outset of the implementation of the Wyly offshore system in 1992 through 2005. However, there is no evidence that Dee participated in the securities fraud. While she may have benefited from it, that alone is insufficient for it to constitute a badge of fraud against her here,
c) The Failure to Take Action to Resolve the Conflicting Advice Sam and Charles Received Regarding the 1992 IOM Trusts
In his role as the Wylys’ primary outside lawyer, French handled the details and was fully authorized to hire and consult with specialist advisors when he considered it necessary.
As was found in the SEC Action, and was independently established here:
[i]n 1993, French approached the law firm of Morgan, Lewis & Bockius (“Morgan Lewis”) to- discuss whether the Bulldog Trust was ‘a grantor or non-grantor trust.’ Morgan Lewis prepared a memorandum concluding 1) that there was a ‘significant risk that the [Bulldog]*414 Trust will be characterized as a grantor trust under § 679 [because] income is being currently accumulated for the benefit of U.S. beneficiaries,’ and 2) that ‘[i]t is also likely that the Trustee’s power to add or substitute other foreign charities (within the class [of beneficiaries]) causes the Trust to be characterized as a grantor trust under § 674. Charles Lu-bar, the partner at Morgan Lewis retained to work on this matter, gave the memorandum to French and spoke with him about its conclusions.394
To amplify this finding a bit based on our record, Lubar was an experienced tax lawyer with impressive credentials. He graduated from Yale University in 1963 magna cum laude, received his JD from Harvard Law School in 1966 and received an LLM in tax from Georgetown University in 1967.
Recall that Sam settled the Bulldog IOM Trust as a foreign non-grantor trust in 1992 and that Charles settled the Pitkin IOM Trust as a foreign non-grantor trust then too. Obviously, if Lubar’s concerns were well-founded, the impact on the Wyly offshore system and the annuity transactions undertaken by Sam and Charles in 1992 created substantial tax problems for them.
On this record there can be no doubt that French was Sam’s and Charles’ agent. French was undoubtedly acting on their behalf when he went to Lubar for a second opinion, as he had been authorized to do, on whether the 1992 IOM trusts settled by Sam and Charles were non-grantor trusts.
Charged with knowledge of these facts, neither Sam nor Charles did anything further themselves, or acting through French, to resolve the conflicting advice they now had from two tax professionals they had hired to give them advice — Tedder and Lubar. And, rather than resolve this legal uncertainty, Sam and Charles continued with the offshore structure in its then form. And, they then chose to expand the offshore structure the following years through the settling of other foreign trusts with falsified documents, which we discuss below, and by continuing to transact business through the offshore system. These facts support the existence of a badge of fraud by clear and convincing evidence from 1993 through 2013 as to Sam and from 1993 through 2011 as to Charles.
However, there is no evidence that Dee ever knew about Lubar’s conclusions— whether in 1993 or in 2003
d) The Creation of False Documents to Support the Settling of IOM Trusts in 1994 and 1995 to Attempt to Obtain Favorable Tax Benefits for the Wylys
The SDNY Court made the following findings and conclusions, which are independently established here:
The following year, French asked Lubar to advise the Wylys about whether a trust settled by “a foreign person who had done business with Sam Wyly” would be treated as a grantor trust. Lubar advised that “as long as there wasn’t an indirect transfer of assets by the U.S. person and the foreign person put the money up, and there were certain powers in the trust, then it would be a foreign grantor trust, and the distributions then would not be taxable.” For the purposes of rendering his opinion, Lubar assumed that the foreign grantor would be the “sole transferor of property to the trust[ ],” unless the taxpayers transferred funds “on an ‘arm’s length’ basis.”401
In 1994 and 1995, two foreign citizens established several trusts for the benefit of the Wylys and their families (collectively, the “Bessie Trusts”). The Bessie*416 Trust and the Tyler Trust were purportedly settled by Keith King, an individual associated with Ronald Buchanan, an IOM trustee selected by the Wylys, with initial contributions of $25,000 each. However, no such contribution was ever made. The trusts “were settled with a factual dollar bill ... plus an indebtedness of $24,999 each on the part of Keith King as settlor.” That indebtedness was immediately forgiven.402
Footnote 107. The 1994/1995 trusts relevant to this Opinion and Order are: 1) the Bessie Trust; 2) the La Fourche Trust; 3) the Red Mountain Trust; and 4) the Tyler Trust. These trusts will be referred to as the “Bessie Trusts,” as per Professor Danforth’s grouping.403
The La Fourche Trust and the Red Mountain Trusts [sic] were purportedly settled by Shaun Cairns, another individual associated with Buchanan, also with initial contributions of $25,000 each. Cairns testified that French prepared letters stating that Cairns was establishing the trusts “to show [his] gratitude for [the Wylys’] loyalty to our mutual ventures and '[their] personal support and friendship;” and asked Cairns to sign them. In truth, Cairns had never met nor dealt with the Wylys before establishing the trusts, and had provided only $100 towards the trusts. Shortly after these trusts were settled, Cairns’s trust management company was hired to serve as trustee for some of the Wylys’ IOM trusts.404
These transactions were shams intended to circumvent the grantor trust rules. French and Buchanan, acting as the Wy-lys’ agents, recruited King and Cairns to create a falsified record of a gratuitous foreign grantor trust. The trust documents are admittedly false — King and Cairns never contributed $25,000 towards the initial settlement.405
There were no gratuitous transfers here. First, I am doubtful that King provided even the factual $1 towards the trusts. In a November 26, 1995 fax to French, Buchanan writes that “Keith never produced the money.” Buchanan explains that the King-related trusts “were settled with a factual dollar bill” only so that “there [was] no question of the[] [trusts], being voidable by reason of the*417 absence of assets” pending the Wylys’ transfer of options. Even if King had contributed the $1, the premise that an unreimbursed dollar bill is sufficient to establish a tax-free foreign grantor trust cannot be taken seriously. Second, Cairns’s transfer of $100 cannot be considered gratuitous because shortly after settling these trusts, he received lucrative work from the Wylys as trustee. Finally, in light of the falsified trust deeds and supporting documentation surrounding these trusts, it would be unjust to consider anyone but the Wylys to be the true grantors of these trusts.406
As was unquestionably established— both here and in the SEC Action — the establishment of the Bessie IOM Trust and the Tyler IOM Trust by King in 1994 and the establishment of the La Fourche IOM Trust and the Red Mountain IOM Trust by Cairns in 1995 was highly irregular from the outset. Of significance, the SDNY Court found that French and Buchanan were acting as Sam’s and Charles’ agents. This Court has given collateral estoppel effect to that finding, but at least as to French, the record here independently supports such a finding — by clear and convincing evidence. Moreover, that French was acting within the scope of that agency when he (i) consulted with Lubar about the potential tax ramifications to U.S. beneficiaries of a foreign trust settled by a non-U.S. person, and (ii) then proceeded to facilitate the implementation of those trusts through false documentation and other acts cannot be questioned.
The law is clear, Sam and Charles, as French’s principals, are charged with French’s conduct in (i) facilitating the creation of the 1994 and 1995 IOM trusts, and (ii) creating false documentation that pur
First, and of significance, the Debtors have never argued that French was not the Wylys’ agent regarding the implementation of the Wyly offshore system. Nor could they. Under Texas law, “an agency relationship arises when the principal consents to the agent acting on the principal’s behalf.”
Second, the evidence here unquestionably established that French was acting as Sam’s and Charles’ agent regarding the implementation of the Wyly offshore system from 1992 until his association with the Wylys’ ended in early 2001.
It is well settled that “a principal is chargeable with notice or knowledge concerning a matter within the scope of the agency, received by his agent while acting within the scope of his authority.”414 Comment b to § 5.03 of the Restatement (Third) of Agency illustrates the operation of, and reasoning behind, this legal rule:415
Imputation charges a principal with the legal consequences of having notice of a material fact, whether or not such fact would be useful and welcome. If an agent has actual knowledge of a fact, the principal is charged with the legal*419 consequences of having actual knowledge of the fact. If the agent has reason to know a fact, the principal is charged with the legal consequences of having reason to know the fact. A principal may not rebut the imputation of a material fact that an agent knows or has reason to know by establishing that the principal instructed the agent not to communicate such a fact to the principal. Imputation thus reduces the risk that a principal may deploy agents as a shield against the legal consequences of facts the principal would prefer not to know.
The Fifth Circuit, citing Texas law, also agrees that “[i]t is a fundamental rule of agency law that notice to the agent constitutes notice to the principal.”
While an agent’s knowledge is not imputed to the principal when the agent is acting in a manner that is actively adverse to that of his principal,
In an attempt to get out from under their agent’s objective acts or conduct here, the Debtors argue that French’s subjective fraudulent intent cannot be imputed to Sam and Charles for piurposes of determining whether Sam and Charles underpaid their taxes in any year with fraudulent intent for purposes of 26 U.S.C. § 66681 The Court agrees that it is improper to impute French’s subjective fraudulent intent .to Sam and Charles
Moreover, relying on the Restatement (Third) of Agency, the Debtors argue that “[i]n other words, imputation is the general rule, but there is an exception ‘when knowledge as distinguished from reason to know is important,’ and circumstances exist where personal knowledge — as opposed to imputed knowledge — is the relevant question.”
For example, the first case cited by the Debtors is Henry v, C.I.R.,
When an accountant or attorney advises a taxpayer on a matter of tax law, such as whether a liability exists, it is reasonable for the taxpayer to rely on that advice. Most taxpayers are not competent to discern error in the substantive advice of an accountant or attorney. To require the taxpayer to challenge the attorney, to seek a ‘second opinion,’ or to try to monitor counsel on the provisions of the [Tax] Code himself would nullify the very purpose of seeking the advice of a presumed expert in the first place. ‘Ordinary business care and prudence’ do not demand such actions.425
The next case cited by the Debtors is Davis v. C.I.R.,
[t]o impute to the taxpayer the mistakes of his consultant would be to penalize him for consulting an expert; for if he must take the benefit of his counsel’s or accountant’s advice cum mere, then he*421 must be held to a standard of care which is not his own and one which, in most cases, would be far higher than that exacted of a layman.427
By way of one last example, the Debtors next cite Haywood Lumber & Min. Co. v. C.I.R.,
As the Debtors themselves acknowledge later in their Post-Trial Brief, “[s]pecial rules have developed in the tax context for purposes of determining how to analyze taxpayer’s relations with their advis-ors.”
taxpayers have no obligation to second-guess or monitor their tax advisors. Because the imputation of knowledge rule that exists in other areas of the law is grounded in the principal’s ability to monitor his agent to ensure compliance with the agent’s duty to transmit material facts to the principal, imputation conflicts with the special tax rule that no monitoring is required.431
The Court agrees with these statements and the holdings of the courts in Henry, Davis, and Haywood Lumber. But, what the Debtors’ arguments overlook is that French was not the Debtors’ specialized tax advisor. French had no specialized competence to address tax matters. That’s why the Wylys looked to, among others, Tedder, Chatzky, Lubar, Owens, Pulman, and Cousins for their tax advice— not French. French was a securities lawyer.
Rather, all the Court is doing is imputing to Sam and Charles certain things their agent, French, did — again, not as their specialized tax advisor, but as their agent charged with responsibility to facilitate the implementation of the offshore system. So what acts did French do in his capacity as the person responsible to facilitate the implementation of the offshore system?
First, French went to Lubar and told Lubar to assume, as relevant here, three facts for purposes of offering his advice on the tax consequences to U.S. citizen bene
Second, after enlisting Buchanan’s help, French asked two virtual strangers to the Wylys — King and Cairns — to settle foreign grantor trusts with $25,000 of King’s and Cairns’ own money per trust — a total of $50,000 for each of them. One must wonder why French would ask virtual strangers to settle the trusts (given the facts he told Lubar to assume were true) or that either King or Cairns would settle trusts with $50,000 of their own money for the benefit of Americans one of them (King) barely knew
Third, after Cairns agreed to settle his trusts, French prepared and had false documents signed to attempt to create a paper record to show that the Cairns-settled trusts “fit” into the proper mold for (i) the establishment of a valid foreign trust by a non-U.S. grantor, and (ii) the Wylys to obtain the tax benefits such a structure would offer. In short, French “papered” the transactions in such a way that the trusts might later withstand scrutiny by the IRS — or so French and his principals, Sam and Charles, hoped.
Fourth, shortly after these trusts were settled, Cairns’ trust management company was hired to serve as trustee for some of the Wylys’ IOM trusts.
Fifth, although the record does not reflect that King received business from the Wylys after settling the Bessie IOM Trust and the Tyler IOM Trust, it does reflect that King had previous dealings with Mav
These acts undertaken by French, acting within the scope of his agency, in order to obtain favorable tax treatment for the Wylys offshore transactions undertaken through the 1994 and 1995 IOM trusts supports the existence of a badge of fraud from the date of the creation of each trust through 2013 as to Sam and from 1992 through 2011 as to Charles.
One final point must be addressed. During closing arguments, the Wylys’ counsel argued that French had gone rogue — out acting on his own without the Wylys’ knowledge. The Court rejects this argument for at least two reasons. First, it is simply incredible that a “trusted ad-visor” — French; in fact, one of the Wylys’ “most trusted advisors”
However, there is no evidence that Dee ever knew about the falsified documents or other things that were done to try to make the 1994 and 1995 IOM trusts fit into the proper mold for a valid foreign trust settled by a non-U.S. person. Moreover, there is no evidence that French was Dee’s agent in connection with the implementation of the offshore system. This badge of fraud does not apply to Dee.
e) The Treatment of the Offshore System as the Wyly Family Piggy Bank
The IRS argues, and the Court agrees, that the Wyly family treated the offshore system as their personal piggy bank, of that there is no doubt on this record. The record is replete with instances where a Wyly family member would purchase an item and, after making the purchase, figure out a way to have it paid for with offshore funds.
A prime example is the purchase of an expensive piece of art, Noon Day Rest, by Cheryl Wyly, Sam’s wife. Cheryl apparently attended an art auction at Sotheby’s in London where she found a painting she liked by a British artist, John Frederick Herring; The invoice is dated July 10, 1996 and the purchaser is shown to be Mrs. Cheryl Wyly, along with the address of their Dallas home.
Attached is language from the Deed of Settlement of the Bessie Trust. This language clearly authorizes a purchase of personal property for personal use or enjoyment in specie by any beneficiary. Unless there is a clear and unequivocal requirement of IOM law (which I doubt), that any such purchase that is specifically authorized by the trust agreement must nevertheless be weighed against the investment returns that could otherwise be obtained on the funds, then I must assume that this transaction is authorized and lawful. If you wish to search for such a legal prohibition, you should do so at your own expense and not that of the Trust.
The Protectors have already recommend [sic ] this transaction. Please advise if you are willing to proceed on that basis in light of the explicit authorization for the transaction contained in the Trust Deed.
We need to resolve this issue at once.
In a rare instance of an offshore trustee pushing back against a recommendation of the Wyly trust protectors (French and Robertson at that time), Buchanan wrote back to Boucher stating his concerns regarding the purchase:
Thank you for your overnight fax.[445 ] We will put in train the necessary actions but we would draw to the Committee of Protectors’ attention that they are recommending the substitution of a very safe, income-producing asset by one which might be difficult to sell at a profit at short 'notice and which generates no income, especially since it is suggested that the Trustees should buy it — through Fugue Limited, which is wholly owned by the Bessie Trust — at 222% of the pre-auction estimated price.
We would therefore ask them to confirm, either directly to us or though you under your delegated authority, that:
they do not believe that the beneficiaries will need the income which the proposed purchase price could have generated in the near or medium-term future,
that [sic] they believe that, over the long term, the painting will gain appreciably more in value than would Treasury Bills with the income reinvested.”
On July 24, 1996, French sent a draft letter back to Buchanan, asking if the draft letter will suffice and, if it will, advising that he will get it signed by Sam.
Then, on July 26, 1996, Sotheby’s reissues an invoice for Noon Day Rest — but now to Fugue Limited, Mr. Ronald Buchanan Esq. C/O Lome House Trust at the trust company’s IOM address.
During his trial testimony, Sam appeared to recall little about the transaction, but when he realized what painting he was being cross-examined about he testified “[i]t’s a Herring. Yeah, we love Herrings.”
Two things stand out about this transaction. First, Cheryl made the purchase as the initial invoice demonstrates. After the fact, the purchase is recharacterized as an offshore purchase. Second, it is the first instance in the record where trust protectors recommend that offshore funds be used to purchase personal property for use by a Wyly family member. When Buchan-nan (the relevant IOM trustee) expresses concern regarding the wisdom of an entity owned by the Bessie IOM Trust making the purchase, he is sharply reprimanded by French and directed to make the purchase, which brings to mind a comment from Sam that an IOM trustee would simply be fired if he failed to follow a Wyly “wish”.
While the record is replete with other instances on the Sam side of the Wyly family, the Court will only discuss one other example in detail and six others briefly before turning to the Charles side of the Wyly family. On January 25, 2000, Hennington emails Owens at the Meadows Owens law firm, copying two of Sam’s children and Boucher, stating:
Evan, Lisa, Laurie and Kelly are planning to purchase a house for their mother using off-shore funds. I think we would like to use the same Texas LLC, Texas Trust and off-shore corp to get this done. The house will cost around $850,000. . I assume we will need her to come in for 1% to the trust. They are coming up with names now and Michelle*426 Boucher is starting the process for the off-shore side. Can you please get someone started ASAP on drawing up these documents. I do not think it should take a lot of time since we have basically done this a few times now. We have told her to give us 2 weeks to have the necessary documents drawn up. I will get you the names in the next few days. Please let me know if there is anything else we should be thinking about. As always, thanks for your help.
Owens responds 20 minutes later:
Will do, with pleasure. Please forward names of mother, offshore company and Texas Trust name, as well as legal description of property, and finally the total capital needed. To which file do you want this billed? If to one of the offshore Trusts, please ask Shari to let me know which one. This is fun!
Two days later, on January 27 Hennington emails Owens again stating:
Here are the names for the entities to do Rosemary Acton’s house that Lisa, Laurie, Evan and Kelly are purchasing.
Offshore corp — Spitting Lion Limited
Domestic Texas Trust — Spitting Lion Management Trust
Domestic Texas LLC — Spitting Lion LLC
Michelle Boucher is going to let me know as soon as the name is approved (I do not think we will have a problem). We are planning to fund $900,000 from off-shore to cover closing costs, etc. I am assuming Rosemary will come into trust with $9,000. Does anyone else need to be co-settlor of the trust? ? Please let me know if you need anything else.
Four days later, on February 1, Hen-nington emails Owens to advise: “they have formed the off-shore entity Spitting Lion Limited. Would you please let me know where the other stuff is or who is working on it so I can bug them. As with everything, it has a short fuse. Thanks.”
There are so many problems captured by this rather simple 4-page exhibit of emails that the Court is almost at a loss where to begin. First, the emails make clear that four of Sam’s children have decided to buy their mother and Sam’s first wife, Rosemary Acton, a house in Dallas. That’s a lovely thought, but they apparently don’t want to use their own money or pay gift tax on their gift to her, so they decide to use offshore funds, which leads us to the second issue. The use of offshore funds is not their decision to make— ie., “Evan, Lisa, Laurie, and Kelly are planning to purchase a house for their mother using off-shore funds,” followed by “[w]e are planning to fund $900,000 from off-shore to cover closing costs, etc.” Rather, it is the decision of the Trustee of the Bessie IOM Trust, which will ultimately own Spitting Lion Limited (IOM), through which this transaction is ultimately undertaken. However, as the emails also make clear, there is not a single thought in anyone’s mind that the offshore Trustee will not simply do as instructed by the Wylys — ie., “Michelle Boucher is starting the process for the off-shore side,” followed by “[w]e have told her [Rosemary Acton] to give us 2 weeks to have the necessary documents drawn up,” and con- • eluding with “I do not think we will have a problem.”
Finally, the Court has puzzled over Owens’ comment in his original reply “This is fun!” For context, the Court understands that Owens was the lawyer who came up with the rather complex structure the Wy-lys used — repeatedly — to bring offshore money back onshore for real estate transactions like this one, where one or more Wyly family member would have the use and enjoyment of the property without it being taxed as a distribution from an offshore trust and without the family member having to pay tax on the value of their use of the property. As one of Owens’ law partners, Pulman, explained in his testimony:
Rodney [Owens] was a very good lawyer and a creative lawyer, and he worked very hard for his clients. Rodney came up with the idea that generally in the real estate area, co-tenants can use property, they both have the right to it, and the use of it is not income from one to the other. So—
Q. Excuse me. Is that under state law or federal law?
A. It’s under state law, but it’s general — it’s co-tenants, joint tenants can use any kind of property, but we were talking about real estate. So the concept was we were going to have a foreign corporation, because of the liability and because of the estate tax, that would be the investor. But then we had to have a structure so we could have co-tenants, but not owning the property directly, so Rodney came up with the idea of this joint manage — of this management trust. And the management trust would own the entity that owns the real estate. And the management trust was structured specifically to say that the — that the grantors — in this case, it would be Sam Wyly and the offshore company— would have the right to use of the property as co-tenants, and that if they withdrew, which either partner had the right to- do at any time, they would get back what they put in, plus their percentage share of the value of the property. So we were trying to structure it so that it was truly a co-ownership arrangement that under state law, whether it would be Texas or Colorado, would have the right as a co-tenant, and the LLCs agreements were also drafted consistently so that the owners — so that the co-grantors or the management trust would have the right to use the property as co-tenants.
Pulman went on to explain that Owens took a personal interest in the Wylys and reviewed all of the work done by other lawyers at Meadows Owens on a Wyly matter.
Turning back to Owens’ “this is fun!” remark, the only realistic inference the Court can draw from this rather unfortunate comment is that Owens thinks it is
This "same structure was used on the Sam side of the family on at least four other occasions — in connection with the Rosemary Circle R Ranch property near Aspen Colorado, for the use and enjoyment of Lisa and Kelly, two of Sam’s daughters; for the Cottonwood I and Cottonwood II condominium purchases in Aspen, also for the use and enjoyment of Kelly (she operates an art gallery on the first floor of the condominium (the Cottonwood I transaction) and apparently has an apartment and office on the second floor of the condominium (the Cottonwood II transaction);
Finally, as found by the SDNY Court, in June 2002, Sam Wyly contacted a broker directly and instructed him to ‘hold on’ to 100,000 shares of TYCO stock, overriding a previous order from the IOM trustee, based on an earlier Wyly recommendation, to sell all TYCO shares.”
Turning to the Charles side of the Wyly family, the same structure devised by Owens was used to bring offshore money onshore to purchase real estate for the use and enjoyment of his and Dee’s children at least twice. First, Little Woody LLC, which was owned by Little Woody Management Trust, which was owned by Little Woody Creek Road Limited (IOM)(98%) and Emily (1%) and Jennifer (1%), which was owned in turn by the Tyler IOM Trust, bought a piece of real estate near Aspen in 2001 (LL Ranch) for the use and enjoyment of Emily and Jennifer, two of Charles and Dee’s daughters.
For other examples of property desired by a family member being purchased by
Q. So, they were given to you in Aspen. Is that right?
A. Right, by my husband.
Q. Now, with respect to this ring and this necklace, it’s fair to say that you didn’t consider anyone else other than yourself as the owner of those two pieces of jewelry. Is that correct?
A. Correct.
Q. And, in fact, do you still possess these items?
A. Yes.
Q. They’re in a safe in your home?
A. Yes.
However, apparently unbeknownst to Dee, Soulieana Limited (IOM), an entity wholly owned by the Tyler IOM Trust, paid for those two pieces of jewelry at Charles’ direction, and Soulieana Limited (IOM) also claims to own those pieces of jewelry, which are kept in Dee’s safe in Dee’s home in Dallas, which home is the same home she shared with Charles when he was alive. Soulieana Limited (IOM) purchased other jewelry that Charles gave Dee and that Dee considers herself to be the owner of.
Moreover, Dee purchased pieces of art from the Huntsman gallery, which were hung in one of her homes — either in Dallas or Aspen, but which were paid for by Soulieana Limited (IOM).
Pursuant to my telephone conversation, please invoice the recent purchase by Dee Wyly as follows:
Soulieana Limited
Lome House Trust Limited
c/o Lome House
Castletown, Isle of Man
British Isles
Each invoice should be accompanied by a picture of the item being purchased. In addition, please send these invoices and the necessary documentation to the attention of Shari Robertson, 8080 North Central Expressway, LB 31, Dallas TX 752-6. The Wyly name should not be noted on the invoices.
If you have any questions, do not hesitate to contact me.
Finally, in late 2000, someone apparently decided it would be a good idea to create a better paper trail, so what the Court will refer to as “possession agreements” were thereafter entered into by the offshore entity who had paid for the items and the person who had selected them and had possession of them in the United States. An example of such a possession agreement between Soulieana Limited (IOM) and Charles is IRS Exhibit 26.
There are many other examples in the record that amply support the finding that Sam, certain of Sam’s family members, and Charles considered the offshore system to be their personal piggy banks, through which they could purchase items using offshore money on a tax-free basis. This badge of fraud is established by clear and convincing evidence as to Sam from 1996 through 2013 and for Charles from 1997 through 2011.
The record, however, does not support such a finding with respect to Dee. Although the record shows that Dee purchased items paid for with offshore funds, her uncontroverted testimony was that (i) she was not aware of this,
f) The Planned Insolvency of Various IOM Corporations that Owed Annuity Obligations
As discussed previously, Sam did six private annuity transactions in 1992 and six more in 1996. Charles did four private annuity transactions in each of those years (though one in 1992 involved Dee). With respect to the 1992 annuity transactions, Sam, Dee, and Charles were each scheduled to begin to receive payments when they reached the age of 65 (which was 1998 for Charles, and 1999 for each of Sam and Dee).
In 2003, Charles began receiving annuity payments,
However, several of the IOM corporations that owed annuity payments to Sam became insolvent, causing them to be unable to pay and causing Sam to forgive those payments and any future payments from them prior to his bankruptcy filing
Sam forgave other annuity obligations owing from IOM corporations. In a letter dated the same day, May 31, 2013, East Baton Rouge Limited (IOM) notified Sam that it was not in a position to make the required annuity payment of $2,467,258 and that it did not anticipate being able to do so in the future.
Similarly, by letter dated October 4, 2013, East Carroll Limited (IOM) notified Sam that it was not in a position to make the required annuity payment of $3,142,095 and that it did not anticipate being able to do so in the future.
Sam and Charles structured the IOM corporations that were liable to make the annuity payments in such a manner that they could manipulate whether annuity payments would be made due to the planned illiquidity or insolvency of the IOM corporations, including by moving funds between the various IOM and Cayman corporations and deciding when loans would be repaid (as discussed below). While the IOM corporations owing annuity obligations to Sam were provided stock options worth at least the value of the annuities they issued, by 2003, Hennington and Boucher advised Sam and Charles, among others, that several of those corporations had insufficient assets to fulfill those annuity obligations.
As a result, and as the Court analyzed the trial record, it wondered about the timing of the forgiveness of these annuity receivables since these IOM corporations had not been able to make a full payment to Sam for years. Specifically, why were the annuity receivables forgiven in 2013? Why were loans not made? The Court has come to an answer — albeit one that shows further efforts to protect the offshore system and family members from creditor collection actions, as explained below.
Given that we know that nothing happened offshore unless Sam or Charles “wished” for it to happen, the Court reasonably infers that Sam “wished” that the letters proposing that the annuity obligations due to him be forgiven be sent to him. So, Sam “wished” for the offers to forgive the annuity receivables to be sent to him and he then accepted the offers he caused to be made. But, why did Sam “wish” for these letters to be sent to him in May and October of 2013? The answer is obvious if you think about it — even briefly. Trial in the SEC Action commenced on March 31, 2014,
Moreover, and as noted previously, other IOM corporations could not fulfill their annuity obligations to Sam by the time Sam filed his Case here in October 2014. Specifically, Audubon Asset Limited (IOM) owed him $43,085,167, Moberly Limited (IOM) owed him $16,519,813, Yurta Faf Limited (IOM) owed him $1,007,096, and Locke Limited (IOM) owed him $9,932,801 in annuity payments.
And, once again, the only credible inference to make from the evidentiary record is that Sam “wished” for (i) Moberly Limited (IOM) to loan money to Greenbriar Limited (IOM) and he dictated the terms of that loan, (ii) the assets that Audubon Asset Limited (IOM) purchased to be purchased, and (iii) the loans that Locke Limited (IOM) made to be made. And, equally clear is that if Sam “wished” for assets to be sold so that his annuity payments could be made, that would happen too. But, Sam does not “wish” for that to happen because that might require a Wyly family member to give up their use and enjoyment of a house, a piece of art, jewelry, or other items of property and, of course, would cause him to pay tax on the annuity payment he then received, while the net receivable after tax would be available to pay to his creditors with allowed claims here. From Sam’s perspective, it is much better to have uncollectable annuity receivables and leave the bulk of the IOM structure in place offshore, which makes it much more difficult for his creditors with allowed claims here to collect on those claims.
In total, Sam has forgiven $60,972,221 in annuity obligations, and will not' collect another $70,544,877 in annuity obligations — all because Sam “wished” for that
It is clear from the evidence that there were concerns about the commencement of annuity payments and the effect of reporting those payments as income on Sam’s and Charles’ tax returns. And, while the record supports an inference that these concerns had existed for some time, they are captured in a memorandum dated June 30, 2003 from Hennington and Boucher to Sam, Charles, Evan, and Donnie Miller.
As you are aware, we have been planning for some time for the commencement of the annuity payments. As we have studied the impact of these payments we have become increasingly concerned with the logistical problems of paying the annuities. Our concerns include the following:
1. When the payments are reported on your 1040, they will be on a separate line on page one for annuity payments. It is almost certain given the large amount of these payments that the reporting will result in an IBS audit. There is also a high likelihood that as a result of this audit the entire structure of the foreign system will be audited by the IRS.
2. As the annuities pay over your lifetime you will pay 35% ordinary tax on all payments. In addition, whatever is not consumed in living expenses will be included in your estate and taxed at up to 55%. See the attached spreadsheet detailing the impact of these taxes.
3. The annuity payments will bankrupt several of the I0M companies, which could bring the validity of the annuity transaction into question.
4. After a few years of payments, the companies will be left with non-liquid assets, which will result in payments being made in-kind. This is mostly the case with real estate, Green Mountain and First Dallas, which cannot be easily liquidated to make payments. It could also be the case with assets that .could be negatively impacted by a liquidation like Michaels, Maverick, or Ranger.
5. The possibility of an in-kind payment raises a few issues. First, the value of the property will be taxed at 1*0% with no resulting cash to pay the tax. Secondly, the acceptance of property in-kind may also call into question the validity of the transaction and the ‘arms-length’ nature of the transaction. The annuities are structured as retirement annuities and most annuitants would not deem non-liquid assets acceptable payment.
From these statements and others made in the June 30, 2003 memorandum, the Court makes several inferences of significance. First, these statements shed light on why Sam and Charles decided to defer receipt of the annuity payments in the first place. Sam and Charles knew that given the amount of the required annuity payments, the reporting of them as income to them on their tax returns would “almost certain[ly]” trigger an IRS audit, something that they had expended great effort (and committed securities fraud) to avoid from the outset.
Indeed, the record is replete with evidence that money was moved from one IOM corporation to another at the whim of the Wylys for a variety of purposes including (i) enabling Security Capital to loan funds to Sam, Charles, and Wyly-related entities,
Finally, the fact that the IOM corporations will become unable to make the payments at all, or will be left with illiquid assets, which will result in in-kind payments being made, will call into question the validity of the annuity transactions and the arms-length nature of those transactions. It goes without saying that getting the wealth associated with the options and warrants, which underlie the annuity transactions, offshore was the primary purpose for establishing the IOM trusts in the first place. Thus, the inability to make annuity payments when due puts the entire system at risk and jeopardizes the enormous tax savings realized through the implementation of the offshore structure.
While these inferences are strongly supported by the record (by clear and convincing evidence), another that the IRS asks this Court to make is not. The IRS argues that the record supports an inference that Sam and Charles never intended to have the offshore corporations obligated on the private annuity contracts make payments to Sam, Dee, and Charles as contractually obligated to do. The Court cannot make thqt leap, as it stretches the record too far. While there is some evidence to support the IRS’ argument at least as of 1996,
Moreover, the Wylys in fact received annuity payments and paid tax on these payments. While the Court is not convinced that Sam and Charles intended from the outset that the annuities never pay out (such that there would never be any income received onshore that would be taxed to them as ordinary income), the Court is satisfied that along the way they had a better idea that was facilitated by their “creative” lawyers — ie., if they could get the money onshore to support their families’ lifestyles through loans to themselves and other family members, direct purchases of assets by IOM entities for the family members’ use and enjoyment, or indirect transfers of offshore funds through a myriad of onshore management trusts and limited liability companies or limited partnerships (and do it tax free if Owens was correct), they simply didn’t need to bring the money onshore through the mechanism originally intended — ie., the annuity payments, which everyone agreed would be taxable to them at ordinary income rates.
The Court asked a question in closing that is of significance to it in evaluating this badge of fraud, which question could not be, or was not, answered by Debtors’ counsel — where is the money that should have been available offshore to make the annuity payments to Sam when they came due? If there was a legitimate explanation — frankly, even a bad explanation — for where the money went the Court wanted to hear it. But, when questioned, the Debtors’ various counsel could only state that they were not aware of any evidence in the record showing where the money went.
In the absence of direct evidence tracing
However, there is simply insufficient evidence in the record to support the application of this badge of fraud to Dee. Although a document was admitted at trial that indicates that Dee forgave an annuity obligation owed to her through Stargate Investments (Texas), for the reasons explained below, the Court concludes that there is no evidence in the record that supports a finding that Dee understood the import of this document. Thus, this badge of fraud does not apply to Dee.
For context, the Court notes that Dee’s receipt of annuity payments works differently than Sam’s. Recall that Dee and Charles assigned all of their rights to receive annuity payments from the various IOM corporations that were a part of Charles’ offshore system to Stargate Investments (Texas).
One of the private annuity agreements assigned to Stargate Investments (Texas) was between Dee and Rugosa Limited (IOM).
There is little evidence in the record regarding the Scheme of Arrangement other than: (i) it exists, and (ii) Dee signed it. While Dee testified that her signature appears on the document, she also credibly testified that she had no knowledge of the information that was referenced in it.
In order for the Court to conclude that this badge of fraud applies to Dee, the Court would have to conclude that Dee understood the effect of the Scheme of Arrangement. Based on Dee’s uncontro-verted testimony during trial that she had no involvement in the family’s financial affairs and no understanding of the offshore system, the Court cannot so conclude. For these reasons, this badge of fraud does not apply to Dee.
g) Understatement of Income
As reflected in the Computation Stipulations, Sam understated his income in the following tax years: 1992 through 2003, 2005 through 2006, 2010.
Accordingly, this badge of fraud is present for the listed years, unless it requires some sort of intentional for deliberate conduct, to which we now turn. For the reasons explained below, the Court con-
Sam argues that, “to constitute a badge of fraud, underpayment of income must be knowing or deliberate.”
Common sense concerns also cut both ways on this issue. On the one hand, underpayment of tax — which necessarily comes about by way of understatement of income or overstatement of deductions — is itself an element of civil tax fraud under 26 U.S.C. § 666B.
On the other hand, there are also problems with stating that understatement of income must be intentional in order to constitute a badge of fraud. At least one court has pointed out that if it is shown that a taxpayer intentionally understated income, that this is not just a badge of fraud, it is direct proof that fraud has occurred.
However, before we agonize too much over these apparent inconsistencies, we must stress two things. First, the Supreme Court has noted that “any conduct, the likely effect of which would be to mislead or to conceal” can indicate tax fraud.
Sam engaged in intentional understatement of income of a certain, albeit subtle, kind. Although Sam did not do something as simple as omit wages from his return or neglect to report a realized capital gain, he did engage in a subtler form of intentional understatement of income when he deferred and eventually forgave annuity payments contractually due to him from IOM corporations that should have been paid to him. Moreover, Sam’s income was intentionally understated when he manipulated the assets of other of the IOM corporations that owe annuity obligations to him such that those obligations are now uncol-lectible.
At trial, Sam testified that it was his understanding that annuity payments he received from the complicated annuity transactions he entered into in 1992 and 1996 involving the transfer of the options and warrants offshore would be taxed as ordinary income to him when he actually received those annuity payments from the IOM corporation that had received the options and warrants in exchange for issuing an annuity payable to him:
Q. (By Mr. Daniel) Mr. Wyly, how did you understand that taxes will be paid on the assets that were placed into the trust?
A. [By Sam] That taxes would be paid when they were paid back a — in -cash to — on the annuity I received or any other distribution ...
And, despite Sam’s argument that the annuity transactions were done to simply defer taxes upon the exercise of the options and warrants transferred offshore, not avoid the payment of taxes, Sam then took actions that insured that those taxes would never be paid.
So, where did the cash these IOM corporations realized upon the exercise of the options and the sale of the associated stock go? The short answer is it went wherever Sam “wished” it to go. And, as previously found, Sam “wished” for it to be used to purchase, among other things, (i) domestic real estate on which homes for Wyly family members were built in Texas and Colorado (also using offshore monies), (ii) two floors of the Paragon building in Aspen, which provided Sam’s daughter Kelly with space for her art gallery, a condominium and an office, and (iii) art, jewelry, and other items of personal property, which various members of Sam’s family keep in their homes and continue to use and enjoy today.
By manipulating the IOM corporations and their assets in this way,' Sam intentionally insured that the annuity payments he was due could not be paid to him, thus enabling him to escape his obligation to pay tax on the annuity income he was contractually entitled to receive. And, instead of liquidating assets or otherwise ceasing his families’ extravagant expenditures, Sam deferred all annuity payments due to him for five years.
As previously found, all of this happened because Sam “wished” for that to be the outcome here.
Because Sam deferred his annuity payments in 1998 as part of a scheme to keep the extent of- his offshore system secret from the IRS and then began to excessively manipulate how -funds within the offshore system were used by at least 1999,
Dee’s situation is different. While Charles’ and Dee’s annuity payments were also deferred,
h) Concealment of Income or Assets
It is obvious from the facts already found that the Wylys went to considerable effort to conceal the extent of their offshore assets and activities. There is little to be gained here by repeating this analy
i) Offering False or Incredible Testimony
Sam was not a great witness at trial. His memory was vastly superior on direct examination than it was on cross-examination. He easily remembered events dating back to his childhood in Louisiana; his college years and professors who made an impact on him there; the progression of his wide-ranging business ventures; to concerns over the domestic banking industry in the 1980s, and on and on through events to the present day. However,- on cross-examination, his memory seemed to fail him and he was impeached regularly with either the deposition testimony he gave in connection with the Motions, the testimony he gave during trial of the SEC Action, or documentary evidence.
And, while the Court appreciates that Sam is 81 and suffers from some health issues, the Court accommodated those issues by scheduling Sam’s testimony early each day as his counsel requested in two hour or less increments, which meant Sam’s testimony occurred over nine trial days. Moreover, breaks were taken any time Sam’s counsel or he requested one. And, of course, neither Sam’s age nor his health issues explains the obvious disparity between his ability to recall facts on direct as opposed to cross-examination.
That Sam was an uncooperative witness on cross-examination by the IRS was obvious. That he had to be impeached frequently to get him to admit to fairly obvious facts is equally clear. In fact, given the difficulty in getting Sam to admit facts that were obviously true, the Court encouraged his counsel to offer to stipulate to those facts when Sam was asked a question that he was struggling to crisply answer, assuming it wasn’t more prejudicial to Sam’s case to do so than a patient and tedious cross-examination followed finally by a grudging admission from Sam would be. However, that rarely happened and so a slow and tedious cross-examination of Sam continued for days, with Sam regular
Sam’s obvious reluctance to answer questions asked of him directly reflects poorly on him. As a result, the Court does not have confidence that it can rely on Sam’s testimony to accurately reflect what really transpired here, absent other, disinterested evidence corroborating his testimony.
Attempting to apply this badge of fraud on a year-by-year basis is problematic, as it is less susceptible to that type of breakdown than most of the other badges of fraud.
The Fifth Circuit grappled with these principles in Toussaint v. C.I.R.,
In affirming the tax court’s imposition of fraud penalties for all five of the years at issue there, the Fifth Circuit noted that “in an action for fraud, the honesty of the accused is not only important, it is controlling.”
Similar to the Fifth Circuit in Toussaint, tax court judges have also looked to a taxpayer’s false or incredible testimony
Conversely, while Dee is uninformed on a wide range of business issues and activities, she was credible. The Court is convinced that she testified truthfully; and thus, this badge of fraud does not apply to Dee.
j) Offering Implausible or Inconsistent Explanations of Behavior
It is hard to believe that Sam didn’t know what French was up to on his behalf — both when French (i) received a second opinion from Lubar in 1993 due to French’s lingering concerns about the proper legal characterization of the Bulldog IOM Trust and the resulting tax treatment to the Wylys of the 1992 annuity transactions, and (ii) created false documents to “paper” the 1994 and 1995 IOM trusts in such a way that those trusts would “fit” the mold for foreign grantor trusts of a non-resident alien in order that the Wylys, as beneficiaries of those trusts, could obtain favorable tax treatment for transactions undertaken through them.
While Sam may be an- “idea guy” who hires the best and the brightest to run his ventures or otherwise work for him because they know more about 'the business or their work than he does, as he described himself and as others described him, it is abundantly clear that Sam does not suffer fools gladly. Sam is obviously a very smart man, who is incredibly savvy in the business world and who expects to be kept informed and for things to happen as he directs. You don’t amass the kind of wealth that he was able to amass unless you are smart, savvy, prepared to take risks and cut loose dead weight. That he had no idea what French was doing, or that there were problems associated with the offshore system that was put in place at his direction, is highly unlikely if not unthinkable.
[reasonable and savvy businessmen do not engage in such activity unless it is profitable. Of course it was profitable— by transferring property, including valuable options and warrants, to the trusts, by exercising the options and trading in secret, and using the proceeds to reinvest in other ventures, the Wylys were able to accumulate tremendous tax-free wealth.
It is abundantly clear here that the IOM trustees chosen by Sam (and Charles) did not have an original thought or idea for the last 25 years. Or, if they had had one (and Sam or Charles didn’t like it), they were bullied into acquiescing to a Wyly “wish” under threat of being fired (“removed” in trust speak) if they didn’t go
This badge of fraud has been established by clear and convincing evidence as to Sam from the outset of the offshore system in 1992 through 2013.
As it relates to Dee, the IRS asks this Court to conclude that Dee’s story is equally incredible — but for different reasons. The IRS says she had to have known about what was going on here because, among other things, she: (i) signed some of the documents concerning the offshore system, (ii) signed and filed false and fraudulent tax returns, and (iii) she learned of the Senate investigation of her family’s offshore system but did nothing thereafter. According to the IRS’ theory, once Dee learned of the Senate investigation, she should have asked Charles tough questions and when she wasn’t satisfied, she should have hired independent counsel to advise her with regard to the offshore system and what she needed to do. The Court has several problems with this argument.
First, the IRS asks too much of Dee under the facts and circumstances here. While it is admittedly surprising that after learning of the Senate investigation of her
Second, the IRS assumes that had she consulted independent counsel that counsel would have given her different advice from that Sam and Charles received in 2003 from Meadows Owens regarding the filing of the Form 8275 disclosures with their tax returns. While it is certainly possible that she would have gotten different advice, that conclusion is pure speculation on this record.
Third, the IRS audit of the offshore system was already underway by the time Dee learned of the Senate investigation. It would not be unreasonable for Dee (or her separate counsel) to conclude that the issues would .get resolved there in a reasonable period of time, even assuming Dee was aware of the audit.
Finally, given what the Court has learned about Dee and Charles’ marriage, the Court can infer what would have happened, in all likelihood, if Dee had done as the IRS suggests. She grills Charles, which would have, again in all likelihood, resulted in him simply reassuring her that all was fine — Sam and he had consulted various professionals throughout the time the offshore system was in existence and had been assured that it was legal. By now it is 2005, Dee is about 72 and has been a homemaker for about 50 years during which she knew virtually nothing about the offshore system or Charles’ business affairs. Really — at this point she should have hired her own lawyer to investigate what her husband of 50 years assured her had been amply investigated and was fine? To be honest, that seems the more implausible of the behavior options under the circumstances here.
After carefully considering the evidence, the IRS has failed in its proof of this badge of fraud as to Dee.
k) Filing False Documents.
So, what documents does the IRS claim were false or misleading when filed with it by the Wylys? The IRS argues that: (i) the manner in which the Debtors reported the annuity payments they received from the offshore system on their tax returns was false and misleading, (ii) the Forms 3520 and 3520-A
Throughout trial, the IRS argued that the manner in which the Debtors reported annuity income from the offshore system was misleading. Instead of reporting annuity income on the face of their tax returns on line 16a, which is labeled “Pensions and annuities,”
At trial, a revenue agent involved with the Wylys’ audit, Charles Herrick (“Herrick”) testified that this manner of reporting is unusual — ie., “annuity income is generally reported on Line 1 or on the face of the return. Here it was on a Schedule C, which is unusual.”
In contrast, Hennington explained why Sam, Charles, and Dee reported offshore annuity income in the way that they did. Specifically, she testified that the offshore
In its Amended Proposed Findings of Facts and Conclusions of Law, the IRS argues that this characterization of the offshore annuity payments as self-employment income is specious, because there was no nexus between the income received and the trade or business operated by Sam and Charles.
Hennington’s explanation that the offshore annuity income was subject to self-employment tax is not unreasonable. 26 U.S.C. § 1402 defines “net earnings from self-employment” as “the gross income derived by an individual from any trade or business carried on by such individual” less any applicable deductions.
Although the Court does not here decide whether the Wylys’ annuity payments
The IRS also argues that the manner in which the Debtors went about reporting— or not reporting — their dealings with the offshore system on Forms 3520, 3520-A, and 5471
Moreover, the Forms 3520 and 3520-A that the Wylys did file were, in the context
Although some required Forms 3520 and 3520-A were filed for trusts that had a
From the Court’s perspective, the misleadingly incomplete picture the filed forms provide of the Wyly offshore system when you consider the other forms that were required to be filed, but were not, strongly suggest that Sam and Charles acted with fraudulent intent.
Finally, the IRS argues that the Wylys’ tax returns were false and misleading in two ways — ie., by (i) underreporting their offshore income, and (ii) falsely answering a question on their tax returns. The Court agrees with the IRS with respect to (i) for all tax years in which there was unreported income and agrees with the IRS with respect to (ii), at least with respect to tax years 1992 through 2002 as to Sam and 1992 through 2003 as to Charles and Dee, as explained below.
It is certainly true that the Wylys’ un-derreported their offshore income on their tax returns, as the parties stipulated in the Computation Stipulations. In that sense,
Moreover, it is true that the Wylys’ checked “no” in response to the Form 1040 question “[d]uring [relevant year], did you receive a distribution from, or were you the grantor of, or transferor to, a foreign trust?” from 1992 through 2013 as to Sam and from 1993 through 2013 as to Charles and/or Dee.
. But even without the SDNY Court’s grantor trust determination, checking the “no” box was misleading on their tax returns once Sam and Charles were on notice of Lubar’s advice that there was a significant risk that the 1992 IOM trusts were properly characterized as grantor trusts as to them. While their 1992 tax returns were filed before they were on notice of Lubar’s advice, every other return they filed that checked “no” in response to the Form 1040 question “Mur-ing [relevant year], did you receive a distribution from, or were you the grant- or of, or transferor to, a foreign trust?,” was filed with knowledge of the significant risk that they could be found to be the grantor of a foreign trust that existed during each year from 1993 through 2013.
Equally, if not more, troubling is the fact that even when Sam and Charles knew they had established trusts in the IOM that they intended to be characterized as grantor trusts as to them — ie., all of the trusts involved in the 1996 annuity transactions (Sitting Bull IOM Trust, Tal-lulah IOM Trust, Arlington IOM Trust, and Crazy Horse IOM Trust as to Sam and Maroon IOM Trust, Woody International IOM Trust, and Lincoln Creek IOM Trust as to Charles) — they still checked the box “no.” Again, this made their tax returns false and misleading from 1992-1996, the years in which those trusts were in existence.
But, to be fair, for tax years 2002 through 2013, Sam attached Form 8275 disclosures to his filed tax returns.
The Form 8275 disclosures were substantially identical for both Debtors. Beginning with Sam’s 2002 tax return, the attached Form 8275 disclosure noted that he had created a trust in a foreign country and that — although he did not regard himself as the grantor of the trust — this conclusion might run counter to certain IRS regulations issued in 2000 under 26 U.S.C. § 679, as well as certain statutory provisions of 26 U.S.C. § 674.
Since all that checking the box “yes” on the tax returns would have disclosed is that Sam or Charles and Dee were the grantor of a foreign trust or had transferred property to a foreign trust in a given year, and because the Form 8275 disclosures that the Wylys attached to their tax returns in the years identified above contained that basic information, the Court agrees with the Debtors that they cured their failure to check the correct box on their tax returns, at least from tax years 2002 through 2013 as to Sam and 2003 through 2011 as to Charles and Dee.
In summary and as it relates to Sam, after examining all of the documents that were filed with the IRS that the IRS labels as false or misleading, the Court concludes that (i) Sam’s tax returns were false in the years in which he underreported income (1992-2003, 2005-2006, 2010) and in the years in which no Form 8275 disclosure was attached to his tax returns (1992-2001), and (ii) the Forms 3520 and 3520-A that he filed were false and misleading, particularly in light of the Forms 3520, 3520-A, and 5471 that should have been filed and were not (1992-2013), as the IRS was never provided with an accurate portrayal of Sam’s offshore system until he was forced to disclose the extent of his offshore holdings during the IRS audit. Accordingly, this badge of fraud applies to Sam.
However, this badge of fraud does not apply to Dee, as the Court is satisfied that Dee (i) did not know that the tax returns and other forms she signed that were filed with the IRS were in any way false or misleading, and (ii) did not participate in any decision to attempt to keep the extent of the offshore holdings secret through less than complete and candid repoi’ting.
1) Failure to Cooperate with Taxing Authorities.
The evidence here is conflicting. Certainly, the IRS has pointed to instances where incomplete information was provided to them in connection with an earlier, but unrelated, audit, or where inaccurate information was provided bn a tax return. Overall, however, the Court is persuaded that at least as to the 2004 audit of the offshore system, the one truly relevant here, the Wylys have cooperated with, the taxing authorities.
The IRS has not established this badge of fraud by clear and convincing evidence as to either Sam or Dee,
In conclusion, the IRS has established, by clear and convincing evidence, the following badges of fraud in the following years as to Sam:
As the above summary demonstrates, there are numerous badges of fraud present as to Sam each year from 1992 through 2013. And, as noted previously, while the sheer number of badges is not determinative, the significance of the badges under the facts and circumstances here have convinced the Court that the IRS has carried its burden of proof regarding Sam’s liability for fraud penalties under 26 U.S.C. § 6663 for each year from 1992 through 2013.
However, as explained above, the IRS has not proven, by clear and convincing evidence, the existence of any badge of fraud as to Dee, which is obviously insufficient for it to carry its burden of proof as to Dee. But, the IRS has one final argument in its arsenal that it uses to attempt to prove Dee’s intentional failure to pay taxes known or believed to be owing — i.e., the doctrine of willful blindness, to which we now turn.
C. Was Dee Willfully Blind?
It is undisputed that the doctrine of willful blindness arose in connection with a wide range of criminal statutes. However, in Global-Tech Appliances, Inc. v. SEB S.A.,
Although the tax court has applied the willful blindness doctrine in at least two tax fraud cases to satisfy the knowledge requirement, it is not entirely clear that its application is appropriate here.
When the doctrine of willful blindness has been applied in the criminal law context, it is not always necessary to show that the defendant engaged in affirmative acts to avoid knowledge of wrongdoing to invoke the willful blindness doctrine because “in some cases the likelihood of criminal wrongdoing is so high, and the circumstance surrounding a defendant’s activities and cohorts are so suspicious, that a failure to conduct further inquiry or inspection can justify the inclusion of the deliberate ignorance instruction.”
Assuming that the doctrine of willful blindness applies here, if Dee acted with willful blindness, this Court could find the knowledge requirement for fraud penalties satisfied'. And, while a case could be made that Dee’s conduct here falls more closely into the negligence, carelessness, or foolishness category, the Court will analyze willful blindness to see if it would change the outcome here. Thus, the Court must determine whether it is reasonable to find here — by clear and convincing evidence— that Dee (i) subjectively believed that there was a high probability that she (and Charles while he was alive) had (a) understated income on her (their) tax returns or (b) underpaid her (their) taxes, and (ii) then took deliberate actions to avoid learn
After carefully considering the evidence, this Court concludes that there is insufficient evidence from which a reasonable fact finder could find, utilizing the clear and convincing evidence standard, that Dee subjectively believed that there was a high probability that she (and Charles while he was alive) had (i) understated income on her (their) tax returns or (ii) underpaid her (their) taxes. This is certainly true from 1992 through 2003. During those years, what did Dee know such that she could form a subjective belief of a high probability of understated income or underpaid taxes? At best, the record supports a finding that Dee knew that: (i) Charles had established a series of offshore trusts and related entities in the IOM, (ii) she had signed certain documents in connection with certain of the IOM trusts, the IOM corporations, or her annuity agreements issued by an IOM corporation, (iii) they lived a lavish lifestyle purchasing expensive jewelry, art, and home furnishings, and (iv) she had signed their joint tax returns.
However, on this record, the Court cannot find that Dee: (i) understood the offshore system — complex or not, (ii) understood any of the documents she had signed in connection with the offshore system— which she had not read and the Court is satisfied that if she had read she would not have understood to any great extent, (iii) knew that the items of expensive jewelry, art and home furnishings that Charles and she had purchased had been paid for by one or more of the IOM trusts or corporations, and (iv) understood their joint tax returns — which she had not read and the Court is satisfied that if she had read she would not have understood to any great extent. In point of fact, Dee’s lifestyle did not change after the offshore system was established, which could have put her on notice that something was amiss. By 1990, Charles and she were rich by anyone’s standard and she had become accustomed to a lifestyle that most would consider lavish. She made purchases and someone in the Wyly family office paid the bills. Nothing changed in that regard on or after 1992.
But, even assuming that she knew and understood that Charles had established an extremely complicated offshore system; that, standing alone, is not illegal or fraudulent. Moreover, even assuming that she had read and understood the documents she had signed — nothing in them would have put her on notice of anything that should have created a subjective belief of a high probability that Charles and she had understated their income or underpaid their taxes. Their joint tax returns were extremely complicated documents that she had no role in preparing. From her perspective, they continued to be prepared as they always had — by people within the Wyly family office whom she trusted. From this Court’s perspective, there is simply insufficient evidence to find — by clear and convincing evidence — that Dee knew something that should have created a subjective belief in her that there was a high probability that Charles and she had understated their income or underpaid their taxes during those years.
Now, let’s analyze the later years. An IRS audit focused on the Wyly offshore system started in 2004, the Senate began investigating the Wyly offshore system in 2005,
Again, recognizing that Dee is an intelligent but financially unsophisticated woman, the Court is convinced that she has not understood the legal issues being litigated here (many of which are the same issues that were being investigated elsewhere), which strongly suggests that she would not have understood them in that context either. In short, her three years of college and her 50 plus years as a homemaker and mother did not equip her with the ability to understand the highly complicated legal issues sufficiently such that she could form a subjective belief of a high probability that Charles and she (or she after Charles’ death) had understated their (her) income or underpaid their (her) taxes. And, without such a subjective belief, we do not get to the required second element of willful blindness — ie., that Dee then took deliberate actions to avoid learning of the fact of her (their) understated income or underpaid taxes.
On this record, the IRS failed to prove— by clear and convincing evidence — that Dee was willfully blind; and thus, the IRS has failed to carry its burden of proof on the required second element of its claim for fraud penalties as to Dee for any year in which there is a stipulated underpayment of tax.
D. Is Dee Entitled to the Benefits of the Innocent Spouse Defense ?
Next, the Court must decide whether Dee is entitled to innocent spouse relief pursuant to 26 U.S.C. § 6015 with respect to her liability for any income tax deficiencies that may be determined for the years 1992 through 2011.
As noted previously and as a general rule, when married persons file a joint income tax return they become jointly and severally liable for the tax due with respect to that return. However, Congress concluded that under certain circumstances, such liability could be unfair. As relevant here, Dee seeks “innocent spouse” relief pursuant to 26 U.S.C. § 6015(b) and (c).
For the reasons explained below, this Court is satisfied' that Dee is entitled to innocent spouse relief under § 6015(b), which provides that relief from joint and several liability is available if: (i) a joint return was filed, (ii) there is an understatement of tax attributable to the erroneous items of one individual filing the return, (iii) the spouse requesting relief did not know, and had no reason to know, of the understatement at the time of signing the return, (iv) taking into account all the
As just noted, § 6015(b)’s second required element is that there is an understatement of tax on the return attributable to erroneous items of the other spouse.
As noted previously, the parties have stipulated that there is understated income on Dee and Charles’ joint tax returns for years 1992, 1994 through 2003, 2006, 2008, and 2011.
Section 6015(b)’s third required element is that the requesting spouse establish that, in signing the return, she did not know and had no reason to know that there was such an understatement. A requesting spouse has knowledge or reason to know of an understatement if she actually knew of the understatement, or if a reasonable person in similar circumstances would have known of the understatement.
Courts generally agree on the knowledge test in omitted income cases. For example, in Cheshire v. C.I.R.,
However, in Braden v. C.I.R.,
Another example illustrating omitted income is Pietromonaco v. C.I.R.,
If a spouse has actual knowlédge of the underlying transaction that produced the omitted income, innocent-spouse relief will be denied, even when the spouse did not fully understand the tax significance of the transaction.
With this background in mind, we return to the facts and circumstances to be considered in determining whether a spouse had knowledge or reason to know, including (i) the nature of the item relative to other items, (ii) the couple’s financial position, (iii) the requesting spouse’s educational background and business experience, (iv) the extent of the requesting spouse’s participation in the activity at or before the time the return was signed about items that a reasonable person would question, (v) whether the requesting spouse failed to inquire, at or before the time the return was signed, about items on the return or omitted from the return that a reasonable person would question, and (vi) whether the erroneous item represented a departure from a recurring pattern reflected in prior years’ returns.
After carefully considering the record and the relevant facts and circumstances, the Court is satisfied that (i) Dee did not know about the underlying transactions' that produced the unreported income from the offshore system, and (ii) a reasonable person in similar circumstances would not have known about these transactions. In short, Dee did not have the educational background or sophistication in business and tax matters to know if her tax returns contained any understatements of income. And, a reasonable person with the same educational background and lack of business sophistication as Dee would not have had a different understanding. Accordingly, Dee satisfies the third element for innocent-spouse relief under § 6015(b).
Section 6015(b)’s fourth required element is that, when considering all of the facts and circumstances, it would be inequitable to hold a requesting spouse jointly and severally liable for an understatement.
“Normal support” is not measured absolutely; there is no dollar amount above which support is deemed out of the ordinary. Normal support is determined by comparing the couple in question’s standard of living during the tax years for which there is an alleged deficiency to the years before. If a couple’s standard of living during the tax years in question is beyond what the couple normally enjoyed, that can be evidence of a “significant benefit” that should have put the requesting spouse on notice. As the Fifth Circuit explained in Sanders v. U.S.,
During 1979 and 1980, petitioner clearly lived a very affluent lifestyle. However, prior to 1979, petitioner was already living in the McClure residence, with its pool, clubhouse and tennis court, during one half of the year, and in the furnished Florida condominium during the other half of the year. Petitioner also was already benefitting from the other domestic services of the Robiehauds and the use of the A-frame cabin in Michigan. The extent of the personal use of Tem-Cole’s airplanes prior to 1979 is unclear, but the evidence suggests that Tern-Cole did own airplanes prior to 1979 that were used by petitioner and by Mr. Weasel.
Petitioner’s standard of living during 1979 and 1980 was also not unusual in light of Mr. Weasel’s wealth and level of income. As mentioned, Mr. Weasel had a net worth of approximately $8.6 million in prior years, and he received in prior years annual dividend distributions and compensation totaling over $1 million.693
As with the petitioner in Kistner, Dee experienced no meaningful improvement to her lifestyle during the tax years at issue. As previously found, the Wylys were extremely wealthy before the offshore trusts were established, allowing Dee to enjoy what the IRS characterizes as an opulent lifestyle. And, she continued to enjoy that same lifestyle after the offshore system was established. While the IRS points to purchases of expensive art or jewelry as evidence of “significant benefit” to Dee, as the Treasury Regulations and case law makes clear, significant benefit means something above and beyond the lifestyle the taxpayer previously enjoyed. On this record, it is clear that Dee’s lifestyle did not change in any meaningful way after the establishment of the offshore trusts and related corporations.
In addition to whether the requesting spouse significantly benefitted from the understatement, the tax court has also held that a material factor in determining whether it would be inequitable to hold the requesting spouse liable is whether “the failure to report the correct tax liability on the joint return results from concealment, overreaching, or any other wrongdoing on the part of the nonrequest-ing [sic] spouse.”
[t]he second factor we look at is whether the failure to report resulted from wrongdoing on the part of the nonre-questing spouse. This factor weighs heavily in Linda’s favor. It was, after all, Jerry who embezzled the money, not Linda, and we have already found that she had no reason to know of either the embezzlement or its omission from their return.
Thus, wrongdoing on the non-requesting spouse’s part can weigh in favor of granting innocent spouse relief to the requesting spouse. This is because “[a] purpose of section 6015 relief ‘is to protect one spouse from the overreaching or dishonesty of the other.’ ”
This factor weighs in favor of Dee. This Court previously found that Dee (i) did not commit tax fraud, as none of the badges of fraud it carefully examined applied to Dee,
The regulations interpreting § 6015(b) indicate that there are other factors that may be taken into account when determining whether it would be inequitable under all of the facts and circumstances to hold a requesting spouse liable,
As things presently stand, petitioner and Mr. Von Kalinowski remain married. The two have not separated, and petitioner has not been left by her husband to “face the music”. Instead, petitioner continues to enjoy the lifestyle and financial security that are largely attributable to her, husband’s assets and income. Simply put, petitioner has not been deserted in the sense foreseen by the legislators who enacted the predecessor to the section 6015(b)(1) relief from joint liability.
Normally, it would seem a simple matter to conclude that a widow such as Dee has been left to “face the music” regarding her tax liability on her own. Although Dee still enjoys a great deal of financial security, she has been deprived of Charles’ income, and many of the assets that she previously shared with him are now entangled in his probate estate. However, IRS Revenue Procedures, which are discussed further below, state that a widow or widower will be treated as no longer married for the purposes of the inequity analysis only if he or she “is not an heir to the non-requesting spouse’s estate that would have
Here, although Dee is Charles’ heir, it is unclear whether Charles’ probate estate will have sufficient assets with which to pay the tax liability at issue here. Dee bears the burden of proof on the innocent spouse defense, and since it is unclear on this record whether Charles’ probate estate will be sufficient to pay the tax liability at issue here, the Court cannot conclude that her status as a widow is equivalent to that of divorce or separation for the purposes of the Court’s inequity analysis. Again, however, the tax court has pointed out that “[a]t worst ... widowhood may be a neutral factor” and that it would be completely untenable that this factor weighs against relief.
As to the third factor identified in the regulations — benefit on the return — a “benefit on the return” encompasses situations where the non-requesting spouse’s understatement leads to a tax benefit for the requesting spouse, such as a refund that is higher than that to which the couple would have otherwise been entitled
The regulations interpreting § 6015(b) also advise that “[f]or guidance concerning the criteria to be used in determining whether it is inequitable to hold a requesting spouse jointly and severally liable under this section,” Revenue Procedure .2000-15 “or other guidance published by the Treasury and IRS” is relevant.
While the tax court has considered the Revenue Procedures Factors in determining whether it would be inequitable to hold the requesting spouse liable, it has concluded that they are not controlling.
The Court has already considered the first Revenue Procedures Factor, ’ and agrees with the tax court that widowhood is at worst neutral in the inequity analysis. This factor is neutral as to Dee.
The second factor — economic hardship— is neutral here too. While Dee can certainly pay reasonable basic living expenses even if she is held liable for the tax at issue here given her wealth, the Revenue Procedures provide that “[i]f denying relief from the joint and several liability will not cause the requesting spouse to suffer economic hardship, this factor will be neutral.”
The third factor asks whether Dee was abused. Nothing in the record suggests that Charles abused Dee; in fact, that thought is laughable on this record. But, again, the absence of this factor is neutral.
The fourth factor is whether Dee knew or had reason to know of the items giving rise .to the deficiency at issue. As the Court has already noted in its analysis of § 6015(b)(1)(C), she did not.
The fifth factor asks whether the non-requesting spouse (here Charles) has a
The sixth factor is whether the requesting spouse significantly benefitted from the unpaid income tax liability or understatement. As previously found, this factor weighs in favor of relief for Dee.
The seventh factor inquires whether the liability for which relief is sought is solely attributable to the non-requesting spouse. This factor does not appear in the most recent version of the Revenue Procedures Factors, and in any case was already analyzed by the Court in its discussion of 26 U.S.C. § 6015(b)(1)(B). As previously found, this factor weighs in favor of relief for Dee, but as this factor does not appear in the most current listing of Revenue Procedures Factors and is not analyzed as a Revenue Procedures Factor by those tax courts interpreting the most recent procedures, the Court will not weigh this factor in Dee’s favor.
The eighth factor weighs against relief if the requesting spouse has not made a good faith effort to comply with the income tax laws in the taxable years following the taxable years to which the request for relief relates. This factor weighs against Dee, as there is no evidence in the record indicating that she has “changed course” from the positions that Charles and she took on their joint returns since he passed away. For example, Dee’s tax returns in 2012 and 2013 still continue to indicate that she is not the grantor of a foreign trust.
Finally, the ninth factor asks whether Dee is in poor mental or physical health or was in poor mental or physical health at the time the returns were-filed. There is no evidence that Dee is — or over the time period at issue ever was — in poor mental or physical health. Thus, according to the tax court and the Revenue Procedures, this factor is neutral as to Dee.
After carefully considering all possible factors identified by the courts or the Revenue Procedures, and after carefully considering “all the facts and circumstances” as § 6015(b)(1)(D) instructs it to do,
While the Court does not believe that the fifth element for innocent-spouse relief under § 6015(b) is in dispute here, it concludes that it is satisfied nonetheless. To elect- the application of § 6015(b), a requesting spouse must file Form 8857 (or other similar statement under penalty of perjury containing the same information required on Form 8857) with the IRS no later than two years from the date of the first collection activity against the requesting spouse with respect to the joint tax liability.
For these reasons, the Court concludes that Dee carried her burden of proof and established each of the required elements for innocent spouse relief under 26 U.S.C. § 6015(b). Because the Court has concluded that Dee is entitled to innocent spouse relief under § 6015(b), it need not reach the parties’ arguments about her entitlement to such relief under § 6015(c).
E. Did Sam Establish his Reasonable Cause Defense to the Imposition of Fraud Penalties for His Income Tax Underpayments?
1. The Defense in General
Because the IRS carried its burden of proof on its claim for fraud penalties under 26 U.S.C. § 6663 as to Sam’s underpayments of income tax, we must now analyze his reasonable cause defense. As noted previously, to establish this defense, Sam must prove — by a preponderance of the
(a) In general. No penalty may be imposed under section 6662 with respect to any portion of an underpayment upon a showing by the taxpayer that there was reasonable cause for, and the taxpayer acted in good faith with respect to, such portion. Rules for determining whether the reasonable cause and good faith exception applies are set forth in paragraphs (b) through (h) of this section.
(b) Facts and circumstances taken into account — (1) In general. The determination of whether a taxpayer acted with reasonable cause and in good faith is made on a case-by-case basis, taking into account all pertinent facts and circumstances .... Generally, the most important factor is the extent of the taxpayer’s effort to assess the taxpayer’s proper tax liability. Circumstances that may indicate reasonable cause and good faith include an honest misunderstanding of fact or law that is reasonable in light of all of the facts and circumstances, including the experience, knowledge, and education of the taxpayer. An isolated computational or transcriptional error generally is not inconsistent with reasonable cause and good faith. Reliance on an information return or on the advice of a professional tax advisor or an appraiser does not necessarily demonstrate reasonable cause and good faith. Similarly, reasonable cause and good faith is not necessarily indicated by reliance on facts that, unknown to the taxpayer, are incorrect. Reliance on an information return, professional advice, or other facts, however, constitutes reasonable cause and good faith if, under all the circumstances, such reliance was reasonable and the taxpayer acted in good faith. (See paragraph (c) of this section for certain rules relating to reliance on the advice of others.)
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(c)Reliance on opinion or advice — (1) Facts and circumstances; minimum requirements. All facts and circumstances must be taken into account in determining whether a taxpayer has reasonably relied in good faith on advice (including the opinion of a professional tax advisor) as to the treatment of the taxpayer (or any entity, plan, or arrangement) under Federal tax law. For example, the taxpayer’s education, sophistication and business experience will be relevant in determining whether the taxpayer’s reliance on tax advice was reasonable and made in good faith. In no event will a taxpayer be considered to have reasonably relied in good faith on advice (including an opinion) unless the requirements of this paragraph (c)(1) are satisfied. The fact that these requirements are satisfied, however, will not necessarily establish that the taxpayer reasonably relied on the advice (including the opinion of a tax advisor) in good faith. For example, reliance may not be reasonable or in good faith if the taxpayer knew, or reasonably should have known, that the advisor lacked knowledge in the relevant aspects of Federal tax law.
(i) All facts and circumstances considered. The advice must be based upon all pertinent facts and circumstances and the law as it relates to those facts and circumstances. For example, the advice must take into account the taxpayer’s purposes (and the relative*477 weight of such purposes) for entering into a transaction and for structuring a transaction in a particular manner. In addition, the requirements of this paragraph (c)(1) are not - satisfied if the taxpayer fails to disclose a fact that it knows, or reasonably should know, to be relevant to the proper tax treatment of an item.
(ii) No unreasonable assumptions. The advice must not be based on unreasonable factual, or legal assumptions (including assumptions as to future events), and must not unreasonably rely on the representations, statements, findings, or agreements of the taxpayer or any other person.. For example, the advice must not be based upon a representation or assumption which the taxpayer knows, or has reason to know, is unlikely to be true, such as an inaccurate representation or assumption as to the taxpayer’s purposes for entering into a transaction or for structuring a transaction in a particular manner.
* * *
(2) Advice defined. Advice is any communication, including the opinion of-a professional tax advisor, setting forth the analysis or conclusion of a person, other-than-the taxpayer, provided to (or for the benefit of) the taxpayer and oh which the taxpayer relies, directly or indirectly, with respect to the imposition of the section 6662 accuracy-related penalty. Advice does not have to be in any particular form.
And,, while this regulation does- not expressly refer to fraud penalties under § 6663, the Court believes it has applicability here, as do the parties. Both the Debtors
To establish reasonable cause through reliance on the advice of a tax adviser, the taxpayer must meet the following three-prong test, laid out in Neonatology Assocs., PA. v. Commissioner,115 T.C. at 98 -99: (1) the adviser was a competent professional who had sufficient expertise to justify reliance, (2) the taxpayer provided necessary and accurate information to the adviser, and (3) the taxpayer relied in good faith on the adviser’s judgment.
Some of the same tax courts who use the 26 C.F.R. § 1.6664-4 framework in order to analyze reasonable cause in a fraud context also utilize the Neonatology test in order to assess whether a taxpayer has established reasonable cause based on the reliance on the advice of professionals.
As noted previously, the Debtors assert that their' reliance on the advice of professionals not only establishes a valid reasonable cause defense, but that it also negates the Debtors’ fraudulent intent and prevents the IRS from meeting its initial burden under 26 U.S.C. § 6663.
With this background in mind, Sam’s reasonable cause and good faith defense as to his income tax underpayments fails here, as to all tax years in which there was an underpayment of income tax. In explaining its determination, the Court will first examine what advice Sam received and from whom,
As discussed previously, Sam entered into six .complicated private annuity transactions in 1992, on which he paid no income tax at the time the transactions were undertaken. Sam received a written legal opinion from Pratter, Tedder & Graves dated February 28, 1992 “concerning the 1992 federal income tax consequences that were likely to apply to the proposed sale of ‘Securities’ ... in exchange for a private annuity, with such sale occurring during the 1992 taxable year.”
It is our understanding that you are considering the sale of Securities to a domestic corporation which will issue a private annuity in exchange for the Securities ....
It is our further understanding that the domestic corporation intending to purchase the Securities in exchange for the issuance of the private annuity is wholly owned by a foreign corporation which is wholly-owned by a foreign nongrantor trust.
We also understand that the possession and/or enjoyment of the Securities being exchanged for the private annuity will reside exclusively with the acquiring corporation, and you will not preserve or reserve any control of any kind or character over such Securities or any income therefrom that would constitute a retained interest in the possession and/or enjoyment of the Securities being exchanged for the private annuity. It is thus expressly intended that you will irrevocably surrender the enjoyment, control, ownership, and all economic benefits attributable to the ownership of the Securities which are sold in exchange for the private annuity.
The opinions that were then given by Pratter, Tedder & Graves based upon this factual predicate include, among others, an opinion that: (i) the sale of the Securities in exchange for a private annuity is not a taxable event to Sam in 1992,
[s]hould there be any change in the applicable tax laws or the facts and circumstances relating to the events described herein, the opinions expressed herein necessarily require a reevaluation in the light of such changes....
Our analysis is based on the facts and/or assumptions contained in this letter. If such facts and/or assumptions are inaccurate or incomplete, our analysis and conclusions are equally inaccurate or incomplete and might vary substantially from those contained herein.
Similarly, the six Nevada corporations acquiring the options and warrants from Sam and issuing the unsecured private annuities to him received written opinion letters dated April 2, 1992 from Pratter, Tedder & Graves.
So, as relevant here, taking the February and April opinion letters together, Pratter, Tedder & Graves advised Sam that it is more likely than not that: (i) Sam’s sale of options and warrants to six domestic corporations that were owned by six foreign corporations that were, in turn, owned by a foreign non-grantor trust in exchange for the issuance of a private annuity of equivalent value to him will not trigger income tax or gift tax consequences to him in 1992, and (ii) the subse
There is no dispute here that (i) the domestic corporations — ie., the six Nevada corporations Sam caused to be formed — were wholly owned by the foreign corporations — ie„ the six similarly named IOM corporations that Sam caused to be formed, (ii) the six similarly named IOM corporations were wholly owned by the Bulldog IOM Trust that Sam settled, (iii) the annuity Sam received was of equivalent value to the options and warrants he sold to the Nevada corporations, and/or (iv) the six IOM corporations did not and have not engaged in business within the United States and had no office or agent in the United States. However, another key factual and legal predicate to the 1992 opinion is that the Bulldog IOM Trust, which owned the six IOM corporar tions directly and the six Nevada corporations indirectly, be a foreign non-grantor trust. Surprisingly, there is no Pratter, Tedder & Graves opinion letter, or any other opinion letter, addressing this key predicate to the tax treatment of the 1992 annuity transactions undertaken by Sam. While Sam received opinion letters from Tedder, Chatzky & Berends
With this background in mind, we can now evaluate Sam’s reasonable cause and good faith defense surrounding the income
First, the law is clear that Sam cannot rely upon an opinion of a promoter of the tax scheme in question to support a reasonable cause and good faith defense. When the Court uses the term “promoter,” it is invoking the concept that reliance on a professional “may be unreasonable when it is placed upon insiders, promoters, or .their offering materials, or when the person relied upon has an inherent conflict of interest that the taxpayer knew or should have known about.”
Tax courts have also noted “what exactly makes a tax adviser a promoter has been less than clear.”
Many definitions of “promoter” are negative — ie. they define what a promoter is not as opposed to what a promoter is. One tax court noted that a tax advisor is not a promotor when the advisor (i) has a long-term and continual relationship with the client, (ii) does not give unsolicited advice regarding the tax shelter, (iii) advises only within his field of expertise (and not because of his regular involvement in the transaction being scrutinized), (iv) follows his regular course of conduct in rendering his advice, and (v) has no stake in the transaction besides what he bills at his regular hourly rate.”
The SDNY Court found Tedder to be a promoter in the SEC Action;
Now, to attempt to avoid the well-settled law that he cannot rely upon the advice of a “promoter,” Sam argues that Tedder did not really write the opinions that Tedder signed on behalf of Pratter, Tedder & Graves. Rather, Sam argues that Chatzky actually researched and ghost-wrote the opinions signed and issued by Tedder’s firm. Factually, that is true. Chatzky testified at trial that he wrote the opinions that Tedder’s firm then issued to the Wy-lys. Significantly, however, when asked on direct examination why Tedder signed the opinions instead of him, Chatzky testified that “[his] understanding” was that the Wylys “engaged Pratter, Tedder & Graves to ... draft the opinions and, therefore, the opinions were submitted to David Ted-der for his signature.”
his [Tedder’s] opinion. He can change his mind or he cannot sign it or he can make adjustments or amendments, whatever. And I’m not aware of any such changes that he made. So his [Tedder’s] involvement, really, was to read the opinion and either sign it or' contact me for — with questions.
Ironically, Sam’s own trial testimony makes clear that he was relying on the
But, even assuming that Chatzky gave Sam advice in 1992 and 1993 — ie., the advice contained in the opinion letters he ghost-wrote for Pratter, Tedder & Graves to issue to the Wylys and the offshore entities they caused to be formed in those years, there is no opinion that it is more likely than not that the Bulldog IOM Trust will be construed to be a valid non-grantor trust for United States tax purposes. As noted previously, that was a key factual assumption underlying the 1992 opinions issued 'by Pratter, Tedder & Graves (as ghost-written by Chatzky) to Sam.
Because Tedder’s law firm promoted the offshore system to Sam and Charles, the advice Sam received from Pratter, Tedder & Graves cannot be used to establish a reasonable cause and good faith defense as a matter of law. Moreover, without evidence of the receipt of advice concerning-the legal characterization of the Bulldog IOM Trust as a foreign non-grantor trust, a key factual and legal' assumption underlying the advice received was not established. For either of these reasons, Sam’s reasonable cause and good faith defense fails as to the 1992 annuity transactions in each tax year in dispute among the parties unless Sam received advice regarding the proper legal characterization of the Bulldog IOM Trust as a foreign non-grantor trust thereafter.
Moreover, as discussed previously, French, acting as Sam’s agent, learned in 1993 that Lubar had concluded that there was a “significant risk” that the 1992 IOM trusts — ie., as relevant to Sam, Bulldog IOM Trust, Lake Providence IOM Trust, and Delhi IOM Trust — would be characterized as grantor trusts as to Sam under 26 U.S.C. § 679 because income was being accumulated for the benefit of U.S. beneficiaries.
The record is silent on any other advice actually received by Sam regarding the proper legal characterization of the Bulldog IOM Trust as a foreign non-grantor trust from 1993 to October, 2003. While Meadows Owens — specifically, Owens — began representing the Wylys on tax and estate planning matters in 1998, there is no evidence in the record that Meadows Owens ever independently investigated the proper legal characterization of any of the 1992 IOM trusts as foreign grantor or non-grantor trusts during that time period. And, while Evan testified as to the topics on which Owens gave the Wylys advice at certain Wyly family meetings during this time period, and outlines of discussion topics covered by Owens at those meetings were introduced into evidence at trial,
But even considering Evan’s testimony in this regard, it is not terribly helpful. For example, Evan testified regarding the topics discussed by Owens at a Wyly family meeting in approximately April 2000 as
Similarly, Evan testified about IRS Exhibit 111, another Owen’s discussion outline dated September 7, 2000, confirming that Owens gave advice on each topic, that Sam and he heard the advice, and to the best of Evan’s knowledge, his father followed that advice. .This testimony was similarly unhelpful for the reasons just explained — and another, as explained below.
The Owens’ outline for the September 2000 meeting discusses “Tax Characterization of 1992 Trusts, During Charitable Interest Term” and goes on to state that “[t]he 1992 Trusts are characterized as ‘foreign nongrantor trusts’ [‘FNGT’] for so long as the Grantor is living, plus two (2) years thereafter.”
Finally, and as alluded to previously, what is missing from Evan’s testimony is any detailed understanding of what Owens actually said under each discussion topic
Moreover, even assuming that Owens undertook independent research regarding the 1992 annuity transactions and their tax treatment at this time, we have no idea what facts Owens based his independent analysis and advice upon, as the IRS correctly argues. Sam did not give Owens the facts, nor did Evan. In fact, no witness could articulate the facts upon which any advice Owens gave was based. The best that anyone could do was to say that Owens appeared knowledgeable and that he was given access to anything he needed. For example, Evan testified that Owens “was very well informed on the Isle of Man trusts. We had several family meetings with him where he went into a lot of details on each of the trusts. It was very clear he had a wealth of knowledge regarding those trusts.”
From the Court’s perspective, the fact that Owens appeared knowledgeable is not a sufficient predicate from which the Court can find that his opinions, assuming any relevant to these issues were actually given, were based on adequate facts to make them sound. Lawyers can often appear knowledgeable, but whether they know all the relevant facts that will enable them to give informed and reliable advice is a different question, which simply cannot be answered on this record.
That brings us to 2003. Recall that Boucher learned of Lubar’s 1993 conclusions about the proper legal characterization of the 1992 IOM trusts as grantor trusts as to Sam in 2003 through a chance meeting with him in the Cayman Islands, which led to a flurry of activity as discussed supra at pp. 371-74. Recall that Hennington and Boucher met with Lubar in mid-2003 in London to discuss his conclusions regarding the 1992 IOM trusts and the private annuity transactions undertaken through them in 1992 and that their notes from that meeting are summarized in a memorandum
When this meeting with the IRS had not resolved anything by mid to late September 2003 and Sam’s deadline to file his 2002 tax return was quickly approaching (October 15, 2003), Hennington testified that she turned back to Meadows Owens, who had been advising the Wylys about various aspects of the offshore system and transactions within that offshore system for a few years, for advice on what to do. Specifically, Hennington, acting as Sam’s agent, asked Meadows Owens to advise them what they should do with Sam’s 2002 tax return given Lubar’s conclusions that: (i) the Bulldog IOM Trust “should be classified as a grantor trust because [a] the Trust should be treated as having U.S. beneficiaries and [b] the Trustee may add beneficiaries,”
So, what advice did Pulman and Cousins give the Wylys and. when was it given? First, we know that Pulman testified that they did not have a lot of time to consider the issues as Hennington came to them in late September.
Based on Pulman’s testimony at trial, it appears that he advised Hennington in late October 2003 that he believed the Wylys had a “reportable position”
So, where does this leave us in evaluating Sam’s reasonable cause and good faith defense as to the validity and proper tax treatment of the 1992 annuity transactions? We know that (i) a key assumption underlying the original Pratter, Tedder & Graves opinion to Sam about the tax treatment of those transactions was that the Bulldog IOM Trust be a valid non-grantor trust, (ii) there is no evidence that Pratter, Tedder & Graves actually issued such an opinion to Sam in 1992, 1993, or at any other time, (iii) in 1993 Lubar advised French, acting as Sam’s agent, that there was a significant risk that the 1992 IOM trusts would be characterized as foreign grantor trusts as to Sam, (iv) at least with respect to the Bulldog IOM Trust, there is no advice contrary to Lubar’s from 1993 to mid-2003 when Lubar is asked by Hen-nington and Boucher to do further research and to reanalyze the 1992 transactions, which (a) he does, (b) confirms his original conclusions that the 1992 IOM trusts are properly characterized as foreign grantor trusts as to Sam and Charles,
So, for all of these reasons, Sam has failed to carry his burden of proof to establish his reasonable cause and good faith defense as to the proper legal characterization of the Bulldog IOM Trust and the tax treatment of the 1992 annuity transactions undertaken by him through domestic and foreign corporations indirectly and directly owned by the Bulldog IOM Trust from 1992 through 2013, the years at issue in the Motions and the Claim Objections.
3. The Settlement of the Bessie IOM Trust and the La Fourche IOM Trust and their Proper Characterization
That brings us to Sam’s 1994 and 1995 IOM trusts — ie., the Bessie IOM Trust and the La Fourche IOM Trust. Recall that these trusts were set up as foreign trusts settled by a non-US person — ie., King and Cairns, respectively, and that the Court has already concluded that the settling of these trusts was highly irregular, if not fraudulent, from the outset.
Specifically, by letter dated February 16, 1994, Lubar sent a memorandum to French, as Sam’s agent, on the tax consequences for U.S. beneficiaries of trusts established by a non-resident alien of the United States.
1. The Grantor, although not related to the Taxpayers, has known the Taxpay*495 ers for a considerable period of time and will establish the Trusts for the Taxpayers’ benefit as an entirely gratuitous act. All moneys contributed to the Trusts, now or in the future, will belong to the Grantor, and he has not previously and will not in the future receive any consideration, reimbursement, or other benefit for, or in respect of, this act, directly or indirectly. Further, the Taxpayers have not previously made gifts to the Grantor exceeding US$10,-000 in any taxable year.
2. The Trusts have been established in the Isle of Man as typical discretionary trusts. Under their terms, the trustee (the “Trustee”) has been given broad powers to manage and dispose of the Trusts’ principal and income, subject, in most cases, to the consent of a protector (the “Protector”). Neither the Trustee nor the Protector is a beneficiary of the respective Trusts. The Trusts are irrevocable but may be modified by the Trustee in certain respects, including the naming of additional beneficiaries.
3. The Trusts will acquire a majority share interest in a non-U.S. corporation (“Newco”) organized to engage in, inter alia, the insurance business, exclusively outside the United States. Neither the Taxpayers nor any person related to the Taxpayers, directly, indirectly or constructively,' will transfer any money or other property to Newco except on an “arm’s length” basis [fn 2], and if the Taxpayers provide services to Newco as employees, independent contractors or otherwise, directly or indirectly, they will be compensated solely on an arm’s length basis.
[fn 2] For this purpose, a transfer is considered to be “arm’s length” if undertaken on terms, including financial terms, that would be made between wholly unrelated persons in comparable circumstances.
Based upon these predicate facts, Lubar offers several opinions. As relevant here, Lubar opines that
Because of the broad discretionary powers afforded to the Trustee and the fact that the Grantor is also a beneficiary of the' Trusts, the Trusts will be ‘grantor trusts’ for all U.S. federal income tax purposes pursuant to the provisions of sections 671 et seq. for so long as the Grantor lives. As a consequence, the Grantor will be considered to be the oumer of the portion of the Trusts (including the shares of Newco) attributable to the property that he transfers to the Trusts, and all items of income, deduction or credit attributable to such portion will be included in computing the Grantor’s taxable income and credits for U.S. federal income tax purposes. However, because the Grantor is a nonresident alien as to the United States and neither the Trusts nor Newco will have any income from U.S. sources or effectively connected with the conduct of a U.S. trade or business, the Grantor will have no actual U.S. tax liability or obligation to file a U.S. income tax or information return. In the assumed circumstances, the Grantor will be the sole transferor of property to the Trusts and will, accordingly, be treated as owner of all the interests in the Trusts. Thus, all income of the Trusts will be notionally taxed to the Grantor for U.S. federal income tax purposes, and the Taxpayers, U.S. citizen beneficiaries of the Trusts, will not be subject to U.S. tax on any distributions received from the Trusts that are attributable to income realized by the Trusts during the Grantor’s lifetime .... Further, be*496 cause the Grantor will be treated as owner of the shares of Newco held by the Trusts, the Taxpayers will not be considered to own any shares thereof for purposes of the provisions applicable to “controlled foreign corporations” (“CFC” or “foreign personal holding companies” (“FPHC”) and likely will not be considered to own any shares of Newco for purposes of the “passive foreign investment company (“PFIC”) provisions. Thus, the Taxpayers should not have any current U.S. tax liability or reporting obligations in respect of income realized by Newco during the Grantor’s lifetime (other than compensation that the Taxpayers may receive from newco, directly or indirectly, for services performed on its behalf).
As previously found, certain of those predicate facts were simply not true. Neither King (the grantor of the Bessie IOM Trust) nor Cairns (the grantor of the La Fourche IOM Trust) had known Sam “for a considerable period of time.” Indeed, Evan testified that King was merely a stockbroker who did some business, but “not a lot,” with Maverick.
Q. Is there any language in [the letter] that was not provided to you by Mr. French?
A. No, all of it was provided.
Q. [The letter] says here, “This is to show my gratitude for your loyalty to our mutual ventures and your personal support and friendship.” Were you in fact a friend of Mr. Sam Wyly?
A. No, but I was a friend of Ronnie Buchanan’s.
Q. You never talked to him, never met Mr. [Sam] Wyly?
A. No.
In addition, neither the Bessie IOM Trust nor the La Fourche IOM Trust was established as an entirely gratuitous act.” Indeed, as a stockbroker dealing with Maverick, King had already earned commissions from dealings with Wyly entities (though not through a direct relationship with Sam).
Moreover, as found by the SDNY Court and as independently found here:
*497 There were no gratuitous transfers here. First, I am doubtful that King provided even the factual $1 towards the trusts. In a November 26, 1995 fax to French, Buchanan writes that “Keith never produced the money.” Buchanan explains that the King-related trusts “were, settled with a factual dollar bill” only so that “there [was] no question of the[] [trusts] being voidable by reason of the absence of assets” pending the Wylys’ transfer of options. Even if King had contributed the $1, the premise that an unreimbursed dollar bill is sufficient to establish a tax-free foreign grantor trust cannot be taken seriously. Second, Cairns’ transfer of $100 cannot be considered gratuitous because shortly after settling these trusts, he received lucrative work from the Wylys as trustee. Finally, in light of the falsified trust deeds and supporting documentation surrounding these trusts, it would be unjust to consider anyone but the Wylys to be the true grantors of these trusts.
Indeed, it appears that King’s and Cairn’s failure to fund the trusts was discovered as early as November 1995.
As 26 C.F.R. § 1.6664-4 itself makes clear “the advice must not be based on unreasonable factual or legal assumptions (including assumptions as to future events) and must not unreasonably rely on the representations, statements, findings, or agreements of the taxpayer or any other person.”
For all of these reasons, Sam has failed to carry his burden of proof to establish his reasonable cause and good faith defense as to the proper legal characterization of the Bessie IOM Trust and the La Fourche IOM Trust and the tax consequences attributable to those trusts. In coming to this conclusion the Court has rejected the IRS’ contention that Sam must have actually read the opinions or the memoranda containing the advice he purports to have reasonably relied upon in good faith before he is entitled to assert a reasonable cause and good faith defense. While it is true that Sam admitted that he had not read most, if not all, of those legal opinions or memoranda containing the relevant advice, he is not required to have done so. As the Debtors’ Post-Trial Brief makes clear, the definition of “advice” contained in the applicable regulation allows advice to be provided “to or for the benefit of’ Sam and permits Sam to rely upon that advice “directly or indirectly.”
However, in coming to its conclusion, the Court has also rejected Sam’s argument that he did not know that the factual assumptions contained the opinions or mem-oranda were wrong and that somehow, his lack of understanding allows him to reasonably rely on the advice contained there
4. The 1996 Private Annuity Transactions
We next turn to the six complicated private annuity transactions Sam entered into in 1996, on which he paid no income tax at the time the transactions were undertaken. Recall that those transactions were structured differently from the 1992 annuity transactions. For example, in 1996 Sam assigned 650,000 options to purchase stock of Sterling Software to Crazy Horse IOM Trust, a foreign trust he settled in 1995, which trust immediately assigned the options to Locke Limited (IOM), an entity wholly owned by Bulldog IOM Trust, in exchange for an unsecured private annuity payable to Crazy Horse IOM Trust. Crazy Horse IOM Trust was then liquidated, the effect of which was to put the right to receive the annuity payments to Sam, who as just noted, was the grantor of the now-liquidated Crazy Horse IOM Trust. Sam undertook five more similarly structured annuity transactions in 1996.
We will group the transactions by the IOM trust that owned the IOM entity issuing the private annuity. So, that means that Sam’s two assignments of options to Crazy Horse IOM Trust, which options were then assigned to Locke Limited (IOM) and Moberly Limited (IOM) in exchange for two unsecured private annuities payable to Crazy Horse IOM Trust will be analyzed together, as Locke Limited (IOM) and Moberly Limited (IOM) are both wholly owned by Bulldog IOM Trust. Then, we will analyze Sam’s assignment of options to Arlington IOM Trust, which options were then assigned to Sarnia Investments Limited (IOM) in exchange for an unsecured private annuity payable to Arlington IOM Trust, as Sarnia Investments Limited (IOM) is wholly owned by Lake Providence IOM Trust. Followed by an analysis of Sam’s two assignments of options to Tallulah IOM Trust, which options were then assigned to Audubon Asset Limited (IOM) and Yurta Faf Limited (IOM) in exchange for two unsecured private annuities payable to Tallulah IOM Trust, as Audubon Asset Limited (IOM) and Yurta Faf Limited (IOM) are wholly owned by Bessie IOM Trust. Finally, we will analyze Sam’s assignment of options to Sitting Bull IOM Trust, which options were then assigned to Devotion Limited (IOM) in exchange for an unsecured private annuity payable to Sitting Bull IOM Trust, as it is wholly owned by La Fourche IOM Trust.
Returning to Sam’s two assignments of options to the Crazy Horse IOM Trust, the
[y]ou have requested the law firm of Chatzky and Associates, a Law Corporation to review and comment on the proposed sale of compensatory “Non-qualified Options”.., in exchange for a private annuity, with such sale to occur during the 1996 taxable year for United States income tax purposes and United States income withholding tax purposes.832 ^
Our opinions are based on the correctness of the facts and circumstances set forth herein, and our understanding that the factual scenario set forth hereinbe-low is complete, accurate, true, and correct.833
It is our view based on the information presented to us as expressed herein that it is more likely than not that the anticipated federal United States tax treatment relating to the matters discussed herein will be as we opine herein.834
Then, Chatzky sets forth the facts that the firm is relying upon. Several of those facts are relevant here, including
4. Sam Wyly transferred these options to The Crazy Horse Trust, a foreign situs grantor trust that is recognized as a “grantor trust” for United States income tax purposes.835
5. You anticipate that The Crazy Horse Trust will transfer the non-statutory options to an underlying foreign corporation that is wholly owned by a foreign situs non-grantor trust.836
6. It is anticipated that the wholly owned underlying foreign corporation of a foreign non-grantor trust will issue a private annuity to The Crazy Horse Trust in exchange for the receipt of non-statutory options of an equivalent value.837
Based upon these facts, among others, Chatzky and Associates provides the following opinions
A. Pursuant to the general federal income tax treatment of property exchanged for a private annuity the sale of non-statutory options to a foreign corporation in exchange for The Crazy Horse Trust’s receipt of a deferred private annuity of equivalent value is not a taxable event in the year 1996.838
•f* sC*
B. The private annuity is not intended to contain a gift or bargain sale element,*500 and the exchange of non-statutory options for a private annuity of equivalent actuarial value is likely to be excluded from federal gift tax.839
# * *
C. The annuity payments must be unsecured to avoid immediate taxation of The Crazy Horse Trust in 1996 with respect to the disposition of the non-statutory options in exchange for an annuity of an equivalent value.840 * * *
E. The disposition of compensatory non-statutory options by The Crazy Horse Trust, a grantor trust, in an arm’s length transaction under which non-statutory options are transferred in exchange for the receipt by The Crazy Horse Trust of a substantially nonvested private annuity of an equivalent value Issued by the obligor corporation is not a taxable event in the year 1996.841
* * *
F. The subsequent exercise of the non-statutory options by the obligor will not likely generate a taxable event to The Crazy Horse Trust because the compensation element will remain opened [sic ] until the year The Crazy Horse Trust receives its annuity payments.842
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G. The private annuity contract is likely to be treated as being held by a natural person.843
There is no dispute here that: (i) the Crazy Horse IOM Trust is a foreign situs grantor trust (to Sam), (ii) Locke Limited (IOM) and Moberly Limited (IOM) issued private annuities to the Crazy Horse IOM Trust in exchange for their receipt of the options, and (iii) the annuity was of equivalent value to the options. However, as with the 1992 annuity transactions analyzed supra at pp. 482-94, a key factual predicate to Chatzky’s legal opinion is that the Bulldog IOM Trust, which owned Locke Limited (IOM) and Moberly Limited (IOM), the two corporations issuing annuities to the Crazy Horse IOM Trust, be a foreign non-grantor trust. As discussed at length above, Sam never received any advice that the Bulldog IOM Trust is properly characterized as a foreign non-grantor trust on which he can reasonably rely. As a result, and for the same reasons set forth above in connection with the 1992 annuity transactions, Sam’s reasonable cause and good faith defense fails with respect to these two annuity transactions throughout the tax years in question here.
Turning to Sam’s assignment of options to Arlington IOM Trust, who then assigned those options to Sarnia Investments Limited (IOM) in exchange for an unsecured private annuity payable to Arlington IOM Trust, Arlington IOM Trust also received a written opinion letter from Chatz-ky and Associates
However, a key factual predicate to Chatzky’s legal opinion is that Lake Providence IOM Trust, which owned Sarnia Investments Limited (IOM), the entity issuing the annuity to Arlington IOM Trust, be a foreign non-grantor trust. And, of possible significance to his reasonable cause and good faith defense, on May 19, 1993, Sam received a written opinion letter from Tedder, Chatzky & Berends in which the firm opines that:
[w]e have reviewed this Trust Agreement [for Lake Providence Trust] and have determined that it is more likely than not that the trust will be construed to constitute a valid non-grantor trust for United States taxation purposes provided that the trust operates in accordance with the terms and provisions contained in the Trust Agreement.
So, if this advice is not tainted by Tedder’s status as a promoter of the offshore system to the Wylys, the advice that was missing from the Court’s analysis of the 1992 annuity transactions undertaken through corporations wholly owned by the Bulldog IOM Trust has been supplied. In other words, a key factual predicate in the Chatzky and Associates’ 1996 opinion that the entity issuing the annuity to Arlington IOM Trust be wholly owned by a foreign non-grantor trust may now be satisfied.
But, as already found,
And, without an ability to rely on the May 19, 1993 opinion of Tedder, Chatzky & Berends, the analysis of this transaction and Sam’s reasonable cause and good faith defense is the same as the analysis of the 1992 annuity transactions and Sam’s reasonable cause and good faith defense. As a result, and for the same reasons set forth above in connection with the 1992 annuity transactions, Sam’s reasonable cause and good faith defense fails with respect to this annuity transaction throughout the tax years in question here.
As noted previously, we will analyze Sam’s two assignments of options to Tallu-lah IOM Trust together, as those options were assigned to two IOM corporations— Audubon Asset Limited (IOM) and Yurta Faf Limited (IOM) — that are wholly owned by Bessie IOM Trust. Like the other 1996 annuity transactions just discussed, Tallulah IOM Trust received a written opinion letter from Chatzky and Associates dated February 22, 1996 that is identical to the opinion letter received by the Crazy Horse IOM Trust quoted above except that all references to the Crazy Horse IOM Trust are changed to Tallulah IOM Trust.
However, a key factual predicate to Chatzky’s legal opinion is that the Bessie IOM Trust, which owned Audubon Asset Limited .(IOM) and Yurta Faf Limited (IOM), the corporations issuing the annuities to Tallulah IOM Trust, be a foreign non-grantor trust. Of course, as discussed above, we know that the Bessie IOM Trust was not a foreign non-grantor trust; it was established as a foreign grantor trust (to King) under 26 U.S.C. §§ 671-679.
Finally, we analyze Sam’s assignment of options to Sitting Bull IOM Trust, which assigned the options to Devotion Limited (IOM) in exchange for a private annuity. Devotion Limited (IOM) was wholly owned by La Fourche IOM Trust. Like the other 1996 annuity transactions just discussed, Sitting Bull IOM Trust received a written opinion letter from Chatzky and Associates dated February 22,1996 that is identical to the opinion letter received by the Crazy Horse IOM Trust quoted above except that all references to the Crazy Horse IOM Trust are changed to Sitting Bull IOM Trust.
However, a key factual predicate to Chatzky’s legal opinion is that La Fourche IOM Trust, which owned Devotion Limited (IOM), the entity issuing the annuity to Sitting Bull IOM Trust, be a foreign non-grantor trust. Of course, as discussed above, we know that La Fourche IOM Trust was not a foreign non-grantor trust; it was established as a foreign grantor trust (to Cairns) under 26 U.S.C. §§ 671-679.
5. Alleged Reliance on French
The Debtors assert that they reasonably relied on French, their longtime attorney and advisor, for tax advice regarding the offshore system. The Court disagrees for two reasons. First, the Court finds that French — who is admittedly not a tax lawyer — was not qualified to give tax advice to the Wylys regarding the offshore system. Second, the Court finds that French did not actually give any tax advice of his own to the Wylys regarding the offshore system. Instead, at the Wylys’ request, he acted as a middleman, relaying to them the tax advice of actual tax lawyers he consulted with on their behalf.
That French was acting in a dual capacity here — ie., (i) as the Wylys’ lawyer on issues he was competent to advise on, and (ii) as the Wylys’ trusted agent, empowered to hire other expert advisors with respect to those issues on which he was not, bears brief emphasis. As previously found, French was charged by Sam and Charles, his principals, with the responsibility to oversee the implementation of the Wyly offshore system from a legal perspective. That French was a trusted advisor to the Wylys when the offshore system was initially established and transactions began to be undertaken through it is beyond dispute on this record. However, the Wylys recognized that French did not have the required legal expertise himself to address all of the relevant legal issues that the implementation of the offshore system would require (recall that French was a securities lawyer), so French was authorized to' hire, on the Wylys’ behalf, whomever French believed necessary to implement the offshore system in such a way as to accomplish the Wylys’ goals. And, while French obviously gave some legal advice along the way himself, he was much more than a lawyer here — he served as Sam’s and Charles’ agent, charged with the responsibility to implement the Wyly offshore system. It is in this middleman or agent role that French received tax advice on the Wylys’ behalf from experienced international tax professional(s), but French gave Sam and Charles no tax advice of his own, as he himself acknowledged when he testified that he acted as “basically a business adviser,”
With French’s middleman or agent role firmly in mind, we turn to the first reason tiiat the Wylys’ cannot rely upon French’s purported tax advice — ie., French was not qualified to give tax advice on the offshore system. Whether a particular professional is qualified enough to give tax advice that a taxpayer can reasonably-rely upon is a fact sensitive'inquiry, but that a professional must be at least minimally qualified is beyond question. In certain situations, it will not be enough that the advisor was a lawyer or a certified public accountant.
Neonatology Associates, P.A. v. C.I.R.
for a taxpayer to rely reasonably upon advice so as possibly to negate a section 6662(a) accuracy-related penalty determined by the Commissioner, the taxpayer must prove by a preponderance of the- evidence that the taxpayer meets each requirement of the following three-prong test: (1) the adviser was a competent professional who had sufficient ex*505 pertise to justify rebanee, (2) the taxpayer provided necessary and accurate information to the adviser, and (3) the taxpayer actually relied in good faith on the adviser’s judgment.862
The Neonatology court further noted that it may not be reasonable to rely on a professional’s advice when the taxpayer knew, or should have known, that the professional lacked “the requisite expertise to opine on the tax treatment of the disputed item.”
As a lawyer French is obviously more qualified to give tax advice than an insurance agent who alleged no tax expertise and was not a lawyer. However, this does not necessarily mean that the Wylys could reasonably rely on French’s tax advice, assuming he gave them any. CNT Investors, LLC v. C.I.R.
As of 1999 Mr. Myers had practiced law for almost 30 years, most of them spent in a business-oriented private practice involving some civil litigation. ■ Although he did not hold himself out as a tax lawyer and typically referred clients to specialists for complicated income tax advice, Mr. Myers had taken basic Federal income and estate tax courses in law school, had previously prepared estate tax returns, and had advised Mr. Carroll on general tax law principles,870
Carroll ran into tax problems when he was contemplating retiring and selling his funeral home.
In 1999 Mr. Myers encountered a potential solution. Over lunch with a longtime acquaintance, local financial adviser
*506 Ross Hoffman, Mr. Myers described Mr. Carroll’s problem in general terms, explaining that he had a client who needed to transfer appreciated assets out of a corporation for estate planning .purposes. Mr. Hoffman advised Mr. Myers that he knew of a strategy that might work.
Earlier in the year Mr. Hoffman had attended a Las Vegas conference sponsored by Fortress Financial, a New York-based tax planning firm. Erwin Mayer, an attorney with the law firm Jenkens & Gilchrist, gave a seminar at the conference on a, strategy he called a “basis boost” that could allegedly increase the tax basis of low-basis assets. The basis boost strategy Mr, Mayer presented was, in substance, a Son-of-BOSS transaction.873
Hoffman was not a lawyer and admitted that he did not completely understand the basis boost transaction.
As it turned out, the basis boost transaction was not a legitimate way for Carroll to save taxes, and Carroll found himself in tax court facing significant penalties.
Rather than set a specific standard, the regulations under section 6664(c) outline certain baseline competency requirements. First, rather than mandate that the adviser possess knowledge of relevant aspects of Federal tax law, the regulations stipulate only that “reliance may not be reasonable or in good faith if the taxpayer knew, or reasonably should have known, that the advisor lacked” such knowledge. Sec. 1.6664-4(c)(l), Income Tax Regs. Second, the adviser must base his or her advice on “all pertinent facts and circumstances and the law as it.relates” to them. Id. subpara. (l)(i). Third, the adviser must not himself or herself “unreasonably rely on the representations, statements, findings, or agreements of the taxpayer or any other person.” Id. subpara. (l)(ii) (emphasis added).
In applying these general guidelines, this Court has not articulated a uniform standard of competence that an adviser must satisfy but has instead demanded*507 expertise commensurate with the factual circumstances of each case.880
In the end, the tax court concluded that Carrol could rely on Myers for two reasons. First, Carroll was unsophisticated in financial matters and “had never before invested in even garden-variety mutual funds and securities” and “understood only basic tax principles.”
Mr. Myers performed due diligence. After Mr. Hoffman pitched the Son-of-BOSS transaction to him, in an effort to better understand the proposal Mr. Myers held a conference call with Mr. Mayer. This conversation left Mr. Myers unsatisfied with his grasp of how the transaction would work, so he requested, and Mr. Mayer sent, a memorandum and an article from a tax publication describing and analyzing the transaction and citing various legal authorities. Mr. Myers reviewed Mr. Mayer’s memorandum and consulted some of the legal authorities cited therein, albeit not in extreme detail. He also researched Jenkens & Gilchrist. During the implementation phase, he spoke by telephone with Mr. Mayer several times. Mr. Myers believed that he had a good grasp of how the Son-of-BOSS transaction would work and of the legal theories behind it. Although Mr. Myers did not know all of the details of the transaction, the record does not indicate that he shared this fact with Mr. Carroll. Rather, Mr. Myers formed the opinion that the transaction was “legitimate [and] proper”, and he did share this opinion with Mr. Carroll. He advised Mr. Carroll that the transaction looked like a viable way to resolve CCFH’s low basis dilemma.882
For these reasons, the CNT Investors court concluded that “[t]o Mr. Carroll, a tax and financial layperson, Mr. Myers would have appeared ideal, not simply .competent; to advise him on the feasibility and implications of the basis boost transaction.”
Here, however, Sam’s and Charles’ purported reliance on French presents a situation entirely different from that of CNT Investors. French’s clients, Sam and Charles, were enormously sophisticated businessmen who knew that French was not qualified to give them tax advice on their highly complex offshore system. Moreover, the evidence unquestionably establishes that French did not believe himself qualified to advise the Wylys on the complicated tax issues raised by their offshore system — that is why he chose to consult actual tax specialists on the Wylys’ behalf in order to insure that the tax aspects of their offshore system were properly analyzed and competent advice was given.
As just noted, whether Sam and Charles (and Dee derivatively) could reasonably rely on French’s alleged advice about the offshore system comes down to a facts and circumstances analysis of their situations. And, as found at the outset of. this section of the opinion, after considering those facts and circumstances, the Court finds that Sam and Charles (and Dee derivatively) could not rely on French’s alleged tax advice because: (i) French was not competent to give them such advice as he did not have sufficient tax expertise for them to
Returning to the issue of French’s competence, the Court finds that French was not competent to give the Wylys’ tax advice upon which they could reasonably rely for several reasons. First, French was not a tax lawyer; he was a securities lawyer, as Evan, Sam, and he testified.
Second, the sheer complexity of the Wy-lys’ offshore system made it necessary for French to consult with true tax experts as opposed to attempting to engage in his own tax analysis of the offshore system. That French was not competent to give the Wylys tax advice on the offshore system is corroborated by what he did when faced with uncertainties about the tax consequences associated with the 1992 IOM trusts and the annuity transactions undertaken offshore — i.e., he sought a second opinion from Lubar, a highly credentialed international tax lawyer, both in 1993 and in 1997.
Third, by the time the offshore system was established, both Sam and Charles had many years of experience engaging in highly sophisticated financial transactions. The idea that businessmen as sophisticated as the Wyly brothers could think it was reasonable to rely on a securities lawyer for tax advice regarding their labyrinthine offshore system is not credible. Sam and Charles trusted French as their general counsel, but they knew he was no tax lawyer, as Sam testified: “I don’t recall [French] being concerned about tax things. He was a securities lawyer, basically. He was concerned about disclosures to the SEC and things like that, I think, were his primary mission.”
This brings us to the second reason that the Court finds that Sam and Charles (and Dee derivatively) cannot rely on French in order to establish reasonable cause or a lack of fraudulent intent — i. e., the record does not show that French actually gave any independent tax advice to the Wylys regarding the tax treatment of their offshore system, or at least any independent tax advice upon which they actually relied. The evidence in the record is that most independent investigations into the offshore system French undertook were related to securities law issues, not tax law issues.
Although Evan testified that French worked “as kind of a double-check on the
Regarding the 1994 and 1995 IOM trusts, it is even clearer that French did not independently bless or double-check those structures. In fact, French’s conduct with respect to the establishment of these trusts is highly suspect. French told Lubar to assume certain facts as true that he knew were not true; and then, when Lubar issued advice to the Wylys on how to structure the 1994 and 1995 IOM trusts as foreign grantor trusts to King and Cairns (non-resident aliens of the United States) rather than Sam and Charles based upon those erroneous facts, French proceeded to try to “paper” the transactions in a way that these trusts would “fit the mold” Lubar described, through the drafting of false documents and not insuring that these trusts were actually funded
After a close examination of the record, the Court was only able to uncover one piece of arguably independent tax advice that French gave to the Wylys regarding the offshore system — i.e., that their use of the IOM trusts and corporations as their personal piggy bank could lead to grave tax consequences. French testified repeatedly during the trial in the SEC Action that he told the Wylys — and especially Sam — that controlling the offshore system, for example by using it to purchase assets for use by members of the Wyly family, could have adverse tax consequences.
Q. You’re not a tax lawyer, right?
A. That’s right, but I knew what the tax lawyers said we needed to do.907
As French himself admitted, he was not a tax lawyer, and the Wylys cannot credibly claim that they viewed him as such.
For all of these reasons, the Debtors cannot reasonably rely upon any alleged tax advice they claim French gave them with regard to the offshore system as part of their reasonable cause defenses.
F. Were Gifts Made to the Wylys’ Children?
The parties have stipulated to the transactions that are alleged to constitute gifts here. As to Sam:
Sam Wyly and the IRS stipulate and agree that the property transferred for which the IRS claims gift, tax liability for each of the 2000 through 2005 calendar years is [1] the cash used for the purchase, maintenance, improvement and upkeep of the Cottonwood I and Cottonwood II real estate properties, and [2] the cash and other assets that were transferred into the Cayman LLCs.
As to Dee:
[Dee] & Charles and the IRS stipulate and agree that the property transferred for which the IRS claims gift, tax liability [1] for each of the 2001 through 2005 calendar years is cash used for the purchase, maintenance, improvement and upkeep of the Stargate Sport Horse and the Little Woody (LL Ranch) real estate properties, and [2] for the 2010 calendar year the discharge of a promissory note due to Caroline Dee Wyly from the Caroline D. Wyly Irrevocable Trust.
With these stipulations in mind, the Court will discuss the relevant standards it must
1. The Relevant Standards
a) Defining a Gift
As initial support for its gift theory, the IRS argues, and this Court agrees, that the term “gift” is to be broadly con-stated to cover all transactions in which property or property rights are gratuitously bestowed upon another by whatever means effected.
Transfers reached by the gift tax are not confined to those only which, being without a valuable consideration, accord with the common law concept of gifts, but embrace as well sales, exchanges, and other dispositions of property for a consideration to the extent that the value of the property transferred' by the donor exceeds the value in money or money’s worth of the consideration given therefor. However, a sale, exchange, or other transfer of property made in the ordinary course of business (a transaction which is bona fide, at arm’s length, and free from any donative intent), will be considered as made for an adequate and full consideration in money or money’s worth. A consideration not reducible to a value in money or money’s worth, as love and affection, promise of marriage, etc., is to be wholly disregarded, and the entire value of the property transferred constitutes the amount of the gift.
Moreover, transactions within a family group are subject to special scrutiny, including a presumption that a transfer between family members is a gift.
In Wheeler,[914 ] the government argued that the requirement that a sale be “bona fide” takes on heightened significance in intrafamily transfers and this court agreed. Based on this heightened scrutiny, we concluded that a court should inquire beyond the form of a transaction between family members to determine whether the substance justified the claimed tax treatment. However, we made it clear that just because a transaction takes place between family members does not impose an additional requirement not set forth in the statute to establish that it is bona fide. A transaction that is a bona fide sale between strangers must also be bona fide between members of the same family. In addition, the absence of negotiations between family members over price or terms is not a compelling factor in the determination as to whether a sale is bona fide, particularly when the exchange value is set by objective factors. In summary, the Wheeler case directs us to examine whether “the sale ... was, in*514 fact a bona fide sale or was instead a disguised gift or a sham transaction.”
The Court finds that the heightened scrutiny standard in Kimbell and Wheeler is applicable to the transactions at hand, as each entity and individual involved in the transactions is Wyly affiliated and/or Wyly controlled.
On the other hand, the Debtors argue that there are seven factors that must be satisfied before a gift can be found to have been made: (i) a donor is competent to make the gift, (ii) a donee is capable of accepting the gift, (iii) there is a clear and unmistakable intention on the part of the donor to absolutely and irrevocably divest himself of the title, dominion, and control of the subject matter of the gift in prae-senti, (iv) there is an irrevocable transfer of the present legal title and of the dominion and control of the entire gift to the donee, so that the donor can exercise no further act of dominion or control over it, (v) there is a delivery by the donor to the donee of the subject of the gift or of the most effectual means of commanding the dominion of it, (vi) there is acceptance of the gift by the donee, and (vii) the donor did not receive full and adequate consideration for the transfer of the property.
b) Determining the Underlying Substance of the Transaction
In furtherance of its argument, the IRS also relies upon the general tax principal that the incidence of taxation depends upon the substance of a transaction, rather than its form,
(1) The Economic Substance Doctrine
In Klamath Strategic Inv. Fund ex rel. St. Croix Ventures v. U.S.,
In other words, the transaction must exhibit objective economic reality, a subjectively genuine business purpose, and some motivation other than tax avoidance. While these factors are phrased in the conjunctive, meaning, that the absence of any one of them will render the transaction void for tax purposes, there is near-total overlap between the latter two factors.
Overall, “[t]he economic substance doctrine seeks to distinguish between
As to the first Klamath factor, transactions lack objective economic reality if they do not vary, control, or change the flow of economic benefits.
[t]he latter two Klamath factors ask whether the transaction was motivated solely by tax-avoidance considerations or was imbued with some genuine business purpose. These factors undertake a subjective inquiry into whether the taxpayer was motivated by profit to participate in the transaction. Tax-avoidance considerations are not wholly prohibited; taxpayers who act with mixed motives, seeking both tax benefits and profits for their businesses, can satisfy the business-purpose test.
(2) The Substance Over Form Doctrine
The substance over form doctrine provides that the tax consequences of a transaction are determined based 'on the underlying substance of the transaction rather than its legal form. As explained by the Fifth Circuit in Southgate Master Fund, L.L.C.:
Where, as here, we confront taxpayers who have taken a circuitous route to reach an end more easily accessible by a straightforward path, we look to substance over form and tax the transactions for what realistically they are. A court is not bound to accept a taxpayer’s formal characterization of a transaction, even a transaction that has economic reality and substance. The major purpose of the substance-over-form doctrine is to recharacterize transactions in accordance with their true nature.
(3) The Step Transaction D( ctrine
Similar to the doctrines of economic substance and substance over form, the step-transaction doctrine permits a court to collapse various steps in a transaction to determine its true purpose. As explained by the Fifth Circuit in Security Indus. Ins. Co. v. U.S.,
Under the step transaction doctrine, the tax consequences of an interrelated series of transactions are not to be determined by viewing each of them in isolation but by considering them together as component parts of an overall plan. When considered individually, each step in the series may well escape taxation. The individual tax significance of each step is irrelevant, however, if the steps when viewed as a*516 whole amount to a single taxable transaction. Taxpayers cannot compel a court to characterize the transaction solely upon the basis of a concentration on- one facet of it when the totality of circumstances determines its tax status.
Courts in the Fifth Circuit utilize two tests when determining whether to apply the step-transaction doctrine — the “end results” test and the “interdependence” test.
The test most often invoked in connection with the application of the step transaction doctrine is the “end result” test. Under this test, purportedly separate transactions will be amalgamated into; a single transaction when it appears that they were really component parts óf a single transaction intended from the outset to be taken for the purpose of reaching the ultimate result. As the Fifth Circuit has noted, when cases involve a series of transactions designed and executed as parts of a unitary plan to achieve an intended result, the plans will be viewed as a whole regardless of whether the effect of doing so is imposition of or relief from taxation.
A second test for determining whether the step transaction doctrine applies is labeled the “interdependence” test. This test focuses on whether the steps were so interdependent that the legal relations created by one transaction would have been fruitless without a completion of the senes. When it is unlikely that any one step would have been undertaken except in contemplation of the other integrating acts, step transaction treatment may be deemed appropriate.
With these standards in mind, the Court will now focus on the alleged gifts made by Sam to his children, before turning to Dee’s alleged gifts.
2. Understanding the Transactions Alleged to be Gifts by Sam to His Children
An overview of the transactions that allegedly resulted in gifts from Sam to his children are discussed above, see pp. 396-98, 406-07, 425-28, supra. However, due to the complexity of the transactions, certain of those facts are discussed again below for ease of reference.
a) Formation and Funding of the Cayman LLCs
On June 1, 2001, six Cayman Island Exempted Corporations were formed and were wholly-owned by the Bessie IOM Trust — Orange L.L.C. (“Orange”), FloFlo L.L.C. (“FloFlo”), Bubba L.L.C. (“Bub-ba”), Pops L.L.C. (“Pops”), Balch L.L.C (“Balch”), and Katy L.L.C. (“Katy” and collectively the “Cayman LLCs”).
Boucher described the structure of the Cayman-LLC’s to Sam in a fax dated May 8, 2001:
The sub-funds will be Cayman LLC’s [sic ] as subsidiaries of the IOM Trusts. They will not be formal appointments out of the overall trust and will be revocable. They exist as a sub-fund via an informal understanding with the trustee whereby we account for these entities separately and liaise with particular family members regarding the underlying assets.
* % *
Note that Laurie and Kelly both end up with relatively low liquidity. On a fairly short term basis, Kelly will need liquidity to fund construction costs of their home on Two Mile Ranch [n/k/a Rosemary Circle R Ranch], Laurie also -will need near term liquidity for renovation/reconstructions of the Mi Casa property in Dallas. I suggest either reducing or eliminating allocations of particular investments to them now, or leaving the allocations as is, requiring Laurie and Kelly to decide what to sell when the liquidity needs arise.. I don’t see a problem with them selling assets ..back to the overall trust, or in the market when the need arises.
The Cayman LLCs were subsequently formed and one share of each was issued to John Dennis Hunter,
A list of the Cayman LLCs, each associated child, and a general overview of the assets transferred to the applicable Cayman LLCs follows.
b) The Real Estate Holdings
As shown by the above chart, ownership interests in companies that held interests in real estate were a substantial asset of
The structure used for investment in business use property was slightly different.
At trial, Pulman, a Meadows Owens partner involved in the structuring of the real estate transactions, explained the premise for this highly complex ownership structure.
According to Pulman, the issue then became, since the IOM trust does not own the property directly, but through a foreign corporation, there could be imputation
Several pieces of real estate were purchased under the personal use structure, including (i) the residence in Dallas, Texas, where Laurie and her family live, which is owned by Mi Casa LLC (Texas), (ii) the residence in University Park, Texas, where Rosemary Acton lived, which is owned by Spitting Lion LLC (Texas),
For example, Laurie wished to purchase a home in Dallas using the structure she used to build a second home on Rosemary Circle R Ranch, again utilizing offshore funds.
A similar series of events resulted when Evan, Laurie, Lisa, and Kelly wished to use offshore funds to purchase a home for their mother to live in.
This structure was also used in connection with the Rosemary Circle R Ranch
The “Cottonwood Ventures” properties consist of a set of condominium units on two floors of a commercial office building in downtown Aspen, Colorado, known as the Paragon Building. The first floor condominium unit (Unit 1), which is referred to by the parties as “Cottonwood Ventures I,” is used by Kelly to operate two art galleries. The second floor condominium units (Units 4 and 7), referred to by the parties as “Cottonwood Ventures II,” are used as an apartment and an office.
Cottonwood I Limited (IOM) was established on July 14, 2000 and was wholly owned by the Bessie IOM Trust.
Cottonwood II Limited (IOM) was established on July 14, 2000 and was wholly owned by Bessie IOM Trust.
c) Liquidation of the Cayman LLCs
Moving forward, the Cayman LLC’s were placed into voluntary liquidation in 2006. Sam’s children (Evan, Lisa, Laurie, Kelly, Andrew, and Christiana) did not receive any proceeds from the liquidation of the Cayman LLCs,
3. Analysis of Alleged Gifts Made by Sam
The IRS’ arguments regarding the nature of the alleged gifts from Sam to his children are set forth in §§ 2-3 of its PreTrial Brief. From this briefing, the Court had difficulty understanding precisely what the gifts were. And, once the Computation Stipulations were filed shortly before closing argument, it became, clear that the IRS was very troubled by the transfers of offshore (i) cash that was used to purchase, improve, and maintain the Cottonwood Ventures I and II properties, and (ii) cash and other assets into the Cayman LLCs, However, the precise legal theory or theories through which the IRS was attacking these transfers as “gifts” from Sam to one or more of his children was not crisply delineated.
Because the Court was unsure that it fully understood the IRS’ theories as to Sam’s alleged gifts, and it obviously felt the need to understand those theories before attempting to decide the legal issue of whether Sam made any “gift” on which he would owe gift, tax, it pressed the IRS for more precision during closing arguments. At that time, the IRS clarified that, with respect to the transfers of cash used for the purchase, maintenance, improvement, and upkeep of the Cottonwood Ventures I property, gifts from Sam to Kelly allegedly occurred when funds were transferred to Cottonwood Ventures I, LLC.
The Court will now analyze the “gifts” as clarified at closing by the IRS.
a) Cash Used to Purchase, Improve, and Maintain the Cottonwood Ventures I and II Properties
As shown by the parties’ stipulations, multiple millions of dollars were transferred from various IOM corporations to purchase, improve, and maintain the Cottonwood Ventures I and II properties.
In response to the IRS’ gift arguments, Sam directs the Court to the factors it is to consider to determine if a gift occurred, including whether: (i) a donor is competent to make the gift, (ii) a donee is capable of accepting the gift, (iii) there is a clear and unmistakable intention on the part of the donor to absolutely and irrevocably divest himself of the title, dominion, and control of the subject matter of the gift in praesenti, (iv) there is an irrevocable transfer of the present legal title and of the dominion and control of the entire gift to the donee, so that the donor can exercise no further act of dominion or control over it, (v) there is a delivery by the donor to the donee of the subject of the gift or of the most effectual means of commanding the dominion of it, (vi) there is acceptance of the gift by the donee, and (vii) the. donor did not receive full and adequate consideration for the transfer of the property.
In this regard, Sam argues that factors (i), (iii), and (iv), which require Sam to be a “donor” who intended to and did irrevocably transfer present legal title, cannot be met because Sam did not own the assets he purportedly gifted.
Using this rationale, Sam argues that he could not make a gift of the funds transferred from the IOM corporations because he never held legal title to the funds, as he had divested himself of dominion and control. Instead, according to Sam, the funds were held by various IOM corporations and domestic entities, which were, in turn, wholly owned or almost wholly owned, directly or indirectly, by the Bessie IOM Trust, over which the IOM trustee exercised dominion and control.
Thus, to determine whether Sam made a gift to his children, we must first examine whether Sam retained sufficient “dominion and control” over the offshore cash, and ultimately the property purchased, improved, and maintained with that cash; and, if so, did he sufficiently relinquish that dominion and control in order to make a gift, before moving on to the other factors (if necessary). As explained in the Treasury Regulations:
As to any property, or part thereof or interest therein, of which the donor has so parted with dominion and control as to leave in him no power to change, its disposition, whether for his own benefit or for the benefit of another, the gift is complete. But if upon a transfer of property (whether in trust or otherwise) the donor reserves any power over its disposition, the gift may be wholly incomplete, or may be partially complete and partially incomplete, depending upon all the facts in the particular case. Accordingly, in every case of a transfer of property subject to a reserved power, the terms of the power must be examined and its scope determined.
As this Court previously found in analyzing the various badges of fraud related to Sam’s underpayment of income taxes,
As we have discussed previously, when Laurie wanted to purchase a home for her family to occupy in Dallas using offshore funds, she did not contact an IOM trustee, she asked Sam. Once Sam approved the transaction, the Meadows Owens structure was put in place with Hennington’s and
However, based on our record, and largely for the same reason, the Court cannot find that Sam made a gift of the cash used for the purchase, maintenance, improvement, and upkeep of the (i) Cottonwood Ventures I property to Kelly, or (ii) Cottonwood Ventures II property to each of his children. In short, while Sam may have let go of the cash from the offshore system so that the Cottonwood Ventures I and II properties could be purchased, improved, and maintained, he received an asset worth equivalent value back through (i) his control over the Bessie IOM Trust, which indirectly owns the majority interest in those properties, (ii) his control over Cottonwood I Limited (IOM), which is the sole shareholder of Cottonwood Gallery Inc. (Nevada), as it relates to the Cottonwood Ventures I property, and (iii) his status as Co-Manager of Cottonwood Ventures II, LLC (Colorado) as it relates to the Cottonwood Ventures II property, all of which will be explained more fully below.
According to Treasury Regulation § 25.2511-2(b), a gift is complete only when the donor has “parted with dominion and control as to leave in him no power to change its disposition, whether for his own benefit or for the benefit of another.”
It is undisputed that cash from offshore was used to purchase the overwhelming majority interests in the Cottonwood Ventures I and II properties, along with the cash and other assets Kelly and Sam contributed.
An even simpler analysis demonstrates Sam’s continuing control over the Cottonwood Ventures II property after his alleged gift of cash was made to Cottonwood Ventures II LLC (Colorado), which used the cash (in conjunction with other funds) to buy the Cottonwood Ventures II property.
Under these facts, the Court cannot find that Sam made a gift of cash to his children here. While the Cottonwood Ventures I and II properties were purchased using mostly offshore funds, Sam has never given up control over those properties after their purchase. While Kelly has been permitted by Sam to exercise control over those properties day-to-day, Sam can remove her at any time. Moreover, the fact that Kelly and her siblings may use the properties does not make them, or the cash used to purchase, improve, and maintain them, a gift. The Bessie IOM Trust still owns the overwhelming majority of the Cottonwood Ventures I and II properties, albeit indirectly.
The various judicial doctrines espoused by the IRS do not change this determination. As explained by the Fifth Circuit in Klamath,
As to the first factor, the Court must make an objective inquiry from the taxpayer’s vantage point at the time the transaction occurred as to whether the transaction either caused real dollars to meaningfully change hands or created a realistic possibility they would do so.
The remaining Klamath factors, which are a subjective inquiry into whether the parties to the transaction were motivated by any legitimate, non-tax business purpose,
Despite this, the IRS asks the Court to sham the transaction on the general allegation that Sam’s children were allowed to use the properties so they must have received a gift. The Court is simply not willing to so find based on the record before it. From this Court’s perspective, the issue returns to whether Sam exercised sufficient dominion and control over the offshore system and its funds to make a gift, which he did, and whether he completed such a gift, which he did not.
The Court further finds that, in substance, the transactions were not Sam making a gift of cash to Kelly (or any other child). As explained above, while Sam may have given up control over the funds long enough that they could be used to purchase the Cottonwood Ventures I and II properties, he did not give those funds to his children nor did he give up control over the properties purchased, improved and maintained with those funds— ie., the Cottonwood Ventures I and II properties. In essence, the funds were used to purchase a substitute asset still owned today by the Bessie IOM Trust, albeit indirectly. And, although Sam permits Kelly to use and manage the Cottonwood Ventures I and II properties day-today, and all of his children to use the Cottonwood Ventures II property, there is simply no evidence in the record supporting an inference that he gave his children the cash so they could buy the properties and hold legal title to them (indeed, no child has ever held legal property to either property). In short, none of Sam’s children may individually or collectively dispose of the properties or direct the Bessie IOM Trust to dispose of the properties, and if the properties were sold, only Kelly would be entitled to a portion of the sale proceeds commensurate with her ownership interests. And, while offshore funds were also used to improve and maintain
A step-transaction analysis leads to a similar result. When the transactions are considered together as component parts of an overall plan, the non-gratuitous nature of the transaction becomes, apparent. Sam controlled the offshore funds and, at his direction, those funds were used, along with monies contributed by Kelly in accordance with her percentage of ownership, to purchase the Cottonwood Ventures I and II properties, which properties Kelly (predominately) uses rent-free. But, even if the transactions were collapsed to a direct purchase of real estate by the Bessie IOM Trust and Kelly (as to the Cottonwood Ventures I property on a roughly 90% to 10% ratio and as to the Cottonwood Ventures II property on a roughly 98% to 2% ratio), the record still does not reflect that Sam parted with his ability to exercise dominion and control over the assets largely purchased with the offshore cash. In fact, it demonstrates that Sam still maintains control over the assets.
Accordingly, for the reasons set forth above, the Court finds and concludes that the cash used for the purchase, maintenance, improvement, and upkeep of the Cottonwood Ventures I and II properties was not a gift, by Sam to Kelly or any other of his children.
b) Cash and Other Assets that were Transferred Into the Cayman LLCs
The second category of alleged gifts, “cash and other assets transferred into the Cayman LLCs,” are comprised of transfers of (i) ownership interests in the IOM corporations that indirectly own U.S. real estate — Mi Casa Limited (IOM), Spitting Lion Limited (IOM), Rosemary Circle R Ranch Limited (IOM), Cottonwood I Limited (IOM), and Cottonwood II Limited (IOM) (collectively, the “IOM Real Estate Companies”) — from Bessie IOM Trust to one or more of the Cayman LLCs, and (ii) cash, investments, and other financial assets to the Cayman LLCs. As alleged by the IRS, these gifts occurred when the “cash and other assets” were transferred into the Cayman LLCs in 2001.
(1) The Interests in IOM Real Estate Companies
Before June 2001, the Bessie IOM Trust owned 100% of the interests in the IOM Real Estate Companies, other than Rosemary Circle R Ranch (IOM) that was owned by both Bessie IOM Trust and Orange.
According to the IRS, Bessie IOM Trust’s transfer of these ownership interests in the IOM Real Estate Companies to the Cayman LLCs identified above resulted in a gift from Sam, as grantor of the Bessie IOM Trust,
As an initial matter, the Court notes that the transfer of interests in the IOM Real Estate Companies did not involve multiple steps or loans among the various IOM corporations, but was instead a transfer directly from the Bessie IOM Trust to one or more of the Cayman LLCs.
But, it is also true that there was no gift here to any of Sam’s children. Even if this Court steps back and considers the overall substance of the 2001 ownership interest transfers in the IOM Real Estate Companies, the IOM Real Estate Companies were still owned by the Bessie IOM Trust at all times — either directly in part and indirectly in part or entirely indirectly.
The Court is also not persuaded by the IRS’ argument that Sam’s donative intent is shown by the Cayman LLCs allegedly receiving both the ownership interests in the IOM Real Estate Companies and the account receivable related to the transfer of those interests.
As alleged by the IRS, the gift here is the transfer of ownership interests in the IOM Real Estate Companies from Bessie IOM Trust to one or more of the Cayman LLCs in 2001. While those transfers occurred, the transfers were not a gift to one or more of Sam’s children. As was the
(2) Cash and Other Financial Assets Transferred to the Cayman LLCs
The second type of alleged gift is the cash and other financial assets that were transferred into the Cayman LLCs in 2001. As stipulated by the parties, it appears that the scope of these alleged gifts is comprised primarily, if not exclusively, of the assets loaned by Security Capital to the Cayman LLCs in June 2001.
With respect to these transfers, the IRS urges this Court to find that the various “loans” among the IOM corporations, as well as the formation of the Cayman LLCs and the foreign and domestic trusts, were all sham transactions in furtherance of Sam’s scheme to avoid taxes.
Here, there is no evidence to show that any of the obligations were paid and the notes have open maturity dates. There*536 is no indication that any interest was charged or paid. No demand for repayment was ever made. Finally, the ability to repay the loans is also questionable because the majority of the alleged loans were used to develop and maintain real estate, and therefore, there is no cash readily available to make payments on these alleged obligations. Instead, these appear to be nothing more than entries listed on the family financials balance sheet that served to paper over the gifts.
This quote was taken from the IRS’ Amended Proposed Findings of Fact and Conclusions of Law, which the Court directed be filed after the evidentiary record was closed so that all relevant record cites could be included for the Court’s review. However, no supporting record cites were provided by the IRS for these proposed findings. The lack of record cites may be because there is nothing to cite to, as no testimony, promissory notes, or other documents detailing the alleged terms of the loans are found in the record. As noted previously, the IRS bears the burden to prove that Sam made a gift. If the record is deficient, it is the IRS’ problem, not Sam’s.
However, even assuming its proposed findings are supported by the evidence, the IRS still failed to show that the cash and other assets loaned to the Cayman LLCs by Security Capital were gifts by Sam to his children. In fact, there is nothing in the record indicating that Sam relinquished his dominion and control over the assets transferred to the Cayman LLCs, which is particularly apparent with Sam’s two youngest children, Andrew (Balch) and Christiana (Katy). These children did not use offshore funds from the IOM corporations, the Cayman LLCs, or otherwise to purchase homes or other assets, and they are only mentioned in passing in the IRS’ arguments. Overall, there is no credible evidence in the record demonstrating that any child exercised any control over the Cayman LLC “allocated” to him/her or the cash and other assets held by the Cayman LLCs.
While the Court is cognizant of the IRS’ argument that the Cayman LLCs were only liquidated and their assets returned because Sam was under investigation by the SEC and audit by the IRS and had no other choice, the legal impact of that argument makes little sense here. As it relates to the Cayman LLCs, there was nothing for the children “to return” to the offshore system, as they never owned anything and nothing ever “left” the offshore system. The Bessie IOM Trust always owned the Cayman LLCs and it always owned the cash and other assets held in the Cayman LLCs, albeit indirectly.
For all of these reasons, the IRS has failed in its proof that any of the transfers they alleged constituted gifts were actually gifts from Sam to one or more of his children. Because the Court determines that Sam made no gifts as alleged by the IRS, the IRS’ argument that Sam fraudulently failed to file gift tax returns related to these “gifts” is unavailing.
4. Understanding the Transactions Alleged to be Gifts by Dee to Her Children
With respect to Dee, the parties have stipulated that the alleged gifts are: (i) for each of the 2001 through 2005 calendar years, the cash used for the purchase, maintenance, improvement, and upkeep of the Stargate Horse Farm and Little Woody (LL Ranch) real estate properties, and (ii) for the 2010 calendar year, the discharge of a promissory note due to Dee from the Caroline D. Wyly Irrevocable
c) Stargate Horse Farm
“Stargate Horse Farm” is a 95-acre property located in a rural area of Denton County, Texas, near the Dallas-Fort Worth metroplex, on which a state-of-the-art equestrian facility was built and operated to import, breed, train, and .show internationally competitive sport horses.
Charles is looking at establishing a breeding and equestrian training facility with Emily’s involvement. A business plan has been presented, involving the acquisition of approximately 140 acres of land just north of DFW airport. Only 50 acres will be used for the business venture and it is likely that the remaining land will be subsequently sold. Kee-ley [Hennington] and I are consulting Rodney [Owens] to see if we can use a structure similar to that which was used for the gallery in Aspen, thus utilizing foreign assets for the cash injection and contributing Emily’s horses in the same way Kelly contributed the gallery’s inventory stocks. * * * I have not seen it yet, but understand the business plan indicates the business will not likely cash flow for the first few years, and will need ongoing capital. The anticipated initial commitment will be a minimum of $3 Million.
Meadows Owens set up the following ownership structure for Stargate Horse Farm.
As stipulated by the parties, from 2001 through 2005 Stargate Horse Properties, Inc. (Nevada) contributed approximately 98% of the funds required to acquire, construct, and operate Stargate Horse Farm, while Stargate Sport Horse Management LLC (Texas) contributed the remaining
When additional funds were needed to operate Stargate Horse Farm, the partners of Stargate Sport Horses, LP (Texas) contributed funds in accordance with the operating agreement.
As noted previously, the IRS alleges that Dee (and Charles) made gifts to Emily of all the cash used for the purchase, maintenance, improvement, and upkeep of Stargate Horse Farm, with the gift being complete when the funds were transferred to Stargate Sport Horses, LP (Texas), the entity controlled by Emily.
d) Little Woody (LL Ranch)
“LL Ranch,” also known as Little Woody, is a 26-acre property with a residence near Aspen, Colorado that was initially acquired and owned by Little Woody, Ltd., a Texas limited partnership (“Little Woody, Ltd. (Texas)”).
From 2001 through 2004, Little Woody Creek Road Limited (IOM) contributed 98% of the funds transferred to Little Woody Management Trust (US), while Emily and Jennifer contributed 1% each of the funds transferred to Little Wood Management Trust (US).
The IRS alleges that Dee (and Charles) made gifts to Emily and Jennifer of all the cash used for the purchase, maintenance, improvement, and upkeep of LL Ranch, with the gifts being complete when the funds were transferred to Little Woody LLC (Colorado).
5. Analysis of the Alleged Gifts Made by Dee
a) Cash Used for the Purchase, Maintenance, Improvement, and Upkeep of the Stargate Horse Farm and Little Woody (LL Ranch) Real Estate Properties
As did Sam, Dee argues that the IRS failed to prove the necessary elements of a gift,
Further, even if Dee could have gifted the assets, the record clearly shows that she did not, as the assets (whether in the form of cash or real estate) remained within the Wyly offshore system. It is undisputed that offshore cash was used to purchase the overwhelming majority interest in Stargate Horse. Farm and the LL Ranch property, along with the cash and other assets that Emily contributed in the case of Stargate Horse Farm and the cash that Jennifer and Emily contributed in the case of LL Ranch. And, while Emily may have enjoyed day-to-day control over Star-gate Horse Farm, the record clearly establishes that Charles retained control over the farm as a legal matter from the day it was purchased until it was sold
Granted, while investing in U.S. real estate using the structure set up by Meadows Owens may not be the best business decision of the trustee of the Tyler IOM Trust (as controlled by Charles), it does not change the fact that, in the end, the trust owned the overwhelming majority of Stargate Horse Farm until it was sold and still owns the overwhelming majority of the LL Ranch property and the improvements made to it, albeit indirectly.
That the alleged recipients of the gifts did not/do not hold legal title to the real estate and did not/do not have the right to retain the proceeds upon a sale (except in accordance with their written agreements) is amply demonstrated by the sale of Star-gate Horse Farm in 2009, which, as noted previously, resulted in the distribution of net sale proceeds in accordance with the various operating agreements, with approximately 91% of the funds returning to the IOM offshore system. Under these facts, the Court is hard-pressed to see how Dee could have made a gift to Emily, when the funds were returned to the IOM system in proportion to the parties’ respective investments when Stargate Horse Farm was sold.
This same reasoning applies to Charles. Although the record shows that Charles exercised sufficient dominion and control over the offshore funds and assets to gift them, the Court finds that no such gift occurred. Simply put, there is nothing in the record showing that Charles parted with his dominion and control over the offshore funds and assets to make a gift of them to Emily, in the case of Stargate Horse Farm, and Jennifer and Emily, in the case of LL Ranch. In fact, as previously found with regard to Stargate Horse Farm, Charles retained control over the farm through his ability to control Star-gate Horse Farms Limited (IOM) through his control over the trustee of the Tyler IOM Trust, which had total control over the appointment of directors of Stargate Horse Properties Inc. (Nevada), and these directors in turn had total control over the management of Stargate Horse Properties Inc. (Nevada), which in turn had total control over the management of Stargate Sport Horses LP (Texas), which in turn had control over the management of Star-gate Horse Farm.
Similarly, Charles exercised total control over the LL Ranch property when the gift of cash, as alleged by the IRS, was made. To reiterate, according to the IRS, the gift here was the transfer of approximately $6.2 million of offshore funds to Little Woody LLC (Colorado), which used the cash to purchase, improve, and maintain the LL Ranch property. Little Woody Creek Road Limited (IOM) contributed that cash to Little Woody Management Trust (US) beginning in March 2001 and concluding in November 2004, which then transferred the cash, plus amounts contributed by Emily and Jennifer, to Little Woody LLC (Colorado).
As noted previously, according to Treasury Regulation § 25.2511~2(b), a gift is complete only when the donor has “parted with dominion and control as to leave in him no power to change its disposition, whether for his own benefit or for the benefit of another.”
Further, as was the case with Sam, the various judicial doctrines espoused by the IRS do not change these findings — as to either Dee or Charles.' Even with the application of the substance over form, economic substance, and step-transaction doctrines, this Court must still make an independent assessment of whether the legal elements of a gift exist, which they do not. - Because Dee did not have the legal capacity to make a gift of the offshore funds to her daughters, the Court need not consider whether the transaction had economic substance because, fundamentally, a person cannot gift what they do not own (whether via legal title or, in the case of Sam and Charles, de facto control).
Thus, for the foregoing reasons, the Court finds and concludes that Dee did not make a gift to (i) Emily of the funds used for the purchase, maintenance, improvement, and upkeep of Stargate Horse Farm, and (ii) Emily and Jennifer of the
b) The Promissory Note Due to Dee from the Caroline D. Wyly Irrevocable Trust
(1) Overview of the Transaction
Stargate, Ltd. (“SGL”.), a Texas limited partnership, was formed effective as of December 15, 1992 under the name Brush Creek, Ltd.
Between 1993 and 2007, varying amounts were loaned by SGL to Dee and Charles on an unsecured basis.
Near the end of 1999, Dee and Charles implemented a multi-step estate planning program involving their limited partnership interests in SGL (the “Estate Planning Transactions”). On October 21, 1999, Dee and Charles executed a Marital Agreement dated effective September 30, 1999, pursuant to which they partitioned the community ownership of their limited partnership interests in SGL.
. At this same time, Charles entered into substantially similar transactions, transferring his now-separate property limited partnership interests in SGL to The Charles J. Wyly Irrevocable Trust (the “CJW Irrevocable Trust” and, together with the CDW Irrevocable Trust, the “Irrevocable Trusts”) in exchange for a promissory note in the amount of $25,487,656 (the “CJW Irrevocable Note” and, together with the CDW Irrevocable Note, the “Irrevocable Notes”).
Stargate Investments (Texas) was formed on October 15, 1999.
Generally under this structure, Dee and Charles would make payments to SGL on account of the Unsecured Loan.
According to the Debtors, the Irrevocable Notes were paid in full on October 25, 2010 utilizing the above payment structure, as indicated by the hand-written notation on each note.
The IRS is not convinced that the Irrevocable Notes were repaid, arguihg instead that the circular nature of the payments merely masked the fact that no actual value changed hands, resulting in a gift by Dee to the CDW Irrevocable Trust on October 25, 2010 when the CDW Irrevocable Note was allegedly discharged, but not really repaid.
A chart prepared by the parties depicting the ownership structure and the Charles and Dee Wyly Estate Planning Transactions, is attached to this Memorandum Opinion as Exhibit K
(2) Analysis of the Alleged Gift Made by Dee
The Court initially struggled to understand the true implications of the circular transactions, as each step facially appears proper. Indeed, the IRS does not allege that (i) the Unsecured Loan was not owed by Dee and Charles to SGL, (ii) Dee sold her limited partnership interests in SGL for insufficient value, or (iii) the CDW Irrevocable Note was not a valid promissory nóte. Thus, the circular flow of funds seems appropriate, until one steps back to consider the overall effect.
Normally, when a person sells an asset, as Dee purported to do here — ie., her limited partnership interests in SGL — the purchaser pays for what it bought with its own assets. But, that did not happen here. As the record shows (and as described below), the funds used to pay the CDW Irrevocable Note, which Dee received in exchange for her limited partnership interests in SGL, were funds Dee was entitled to receive from other sources pri- or to the Estate Planning Transactions. Thus, in repayment, Dee received no new value and the res of the CDW Irrevocable Trust was untouched. What did occur was that Dee “sold” her valuable limited partnership interests in SGL to the CDW Irrevocable Trust, which was established for the benefit of her children and grandchildren, without any corresponding benefit to her or tax being paid. These overriding facts must be kept in mind as we wade through the complexity of these transactions and whether they had economic substance as judged under the Klamath factors.
As to the first Klamath factor, the Court must make an objective inquiry from the taxpayer’s vantage point at the time the transaction occurred as to whether the transaction either caused real dollars to meaningfully change hands or created a realistic possibility they would do so.
To illustrate, the Court will trace the first payment made on the Irrevocable Notes through the record. Sometime on or before January 11, 2000, Dee and Charles made an $870,000 payment to SGL on the Unsecured Loan.
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This circular payment arrangement, with all funds used to repay the Irrevocable Notes originating with Dee and Charles (and mostly returning to Dee and Charles), can be traced consistently through the remaining 17 payments made on the CDW Irrevocable Note.
It bears noting how the $870,000 payment on the Unsecured Loan would have flowed before the Estate Planning Transactions. In that instance, Dee and Charles would make a payment to SGL on account of the Unsecured Loan. In turn, SGL would allocate the funds among its partners and make a distribution, with the bulk of the funds returning to Dee and Charles as SGL’s general partners and majority limited partners.
[[Image here]]
The ultimate outcome (money returning to Dee and Charles) is unchanged under either scenario (although more money is returned to Dee and Charles under the pre-Estate Planning Transaction structure), with the difference being ownership of Dee’s (now former) limited partnership interests in SGL having been “sold” to the CDW Irrevocable Trust for the benefit of her children and grandchildren.
The Court' understands that, due to Dee’s and Charles’ affiliation with all of these entities, these are “captive” transactions where money flows back and forth. That, standing alone, does not trouble the Court. What troubles the Court is that the captive system was gamed to get the best' of both worlds — Dee’s limited partnership interests were “sold” to the CDW Irrevocable Trust in exchange for the CDW Irrevocable Note; however, the CDW Irrevocable Trust’s assets were not diminished in repayment of that note. Tellingly, the record shows that, after the Irrevocable Notes were marked paid in full on October 25, 2010, Dee and Charles did not make any further payments on the Unsecured Loan through at least Decem
Simply put, there is nothing in the record objectively indicating that the payment transactions had any economic substance. The transactions did not materially vary control or change the flow of economic benefits
The remaining Klamath factors, whieh are a subjective inquiry into whether the parties to the transaction were motivated by any legitimate, non-tax business purpose,
Accordingly, the Court finds that the alleged payment of the CDW Irrevocable Note lacked economic substance and should be disregarded for tax purposes, resulting in a gift by Dee in an amount not greater than $50,756,841
Alternatively, the Court finds that the alleged repayment of the CDW Irrevocable Note should be recharacterized as a gift for tax purposes under the substance over form doctrine. Although Dee “sold” her limited partnership interests in SGL in exchange for the CDW Irrevocable Note; as detailed above, that note was never actually repaid by the purchaser. Instead, the CDW Irrevocable Note was simply marked paid in full when a sufficient number of circular “payments” were passed through the system. In accordance with the parties’ stipulation, Dee’s gift was in an amount not greater than $50,756,841.
(3) Is Dee Liable for Fraud Penalties on her Gift?
Because the Court finds that Dee made a gift when the CDW Irrevocable
The IRS alleges that Dee deliberately chose not to file gift tax returns because she did not wish to disclose the existence of the offshore corporations and trusts.
While Dee certainly sighed the relevant documents, there is simply no persuasive evidence in the record that Dee understood how these very complicated Estate Planning Transactions worked, or was aware that they would result in her making a gift for which a gift tax return would be required. During trial, Dee credibly testified that she (i) was not involved in Charles’ business affairs, (ii) never discussed business with him, and (iii) trusted him such that when he asked her to sign a document she would, without question. Although she did sign documents involved in the Estate Planning Transactions, she did so without reading them and in full rebanee on Charles. To be clear, even if Dee had read them, the Court is satisfied that she would not have understood them or the gift tax consequences flowing from them.
Further, the Court is hard pressed to see how inadequate records were maintained for the Estate Planning Transactions. To the contrary, it appears that the IRS was provided with ample explanation and documentation regarding the Estate Planning Transactions. For example, Wyly Exhibit PA is a letter from Henning-ton to an internal revenue agent that lays
Thus, for the reasons set forth above, as well as those set forth on pp. 389-462, supra, the Court finds that Dee: (i) made a gift in the 2010 calendar year from the “discharge” of the CDW Irrevocable Note due to her by the CDW Irrevocable Trust in an amount not greater than $60,756,841,
G. Are Penalties Owing for the Failure to File Forms 3520, 3520-A, and 5471?
1. Introduction
In addition to asserting that the Debtors are hable for income tax, gift tax, interest, and fraud penalties, the IRS argues that the Debtors are liable for what are described alternately as international penalties and failure to file penalties (collectively, the “International Penalties”). Although the Court will use the term International Penalties, both descriptions are correct. The International Penalties arise because of the Debtors’ alleged failures to file with the IRS information about the various foreign trusts and corporations that comprise the Wyly offshore system. If applicable here, this information must •be filed -with the IRS pursuant to 26 U.S.C. §§ 6038 and 6048.
The Debtors make three primary arguments in opposition to the IRS’ assertion that it is entitled to recover the International Penalties: (i) that, in many instances, the reporting obligations underlying the International Penalties are not applicable to them because the actions pointed to by the IRS as giving rise to the International Penalties were not violations of §§ 6038 and 6048, (ii) that they have reasonable cause defenses for any violations of §§ 6038 and 6048 they may have committed, and (iii) that the International Penalties are excessive fines under the Eighth Amendment of the Constitution, which should be declared unconstitutional as applied to them if they are both liable for the International Penalties and their reasonable cause defenses fail.
For the reasons explained below, the Court concludes that the Debtors did, in some instances, violate §§ 6038 and 6048, although annuity payments, loans, and real estate transactions originating from the Wyly offshore system did not need to be reported as trust distributions under § 6048(c) and cash sales of options did not need to be reported as transfers into foreign trusts under § 6048(a). The Debtors’ reasonable cause defense and Eight Amendment arguments are addressed in separate sections of this Memorandum Opinion.
2. Statutory Overview
Before addressing the parties’ particular arguments, an overview of the statutes that govern the International Penalties, 26 U.S.C. §§ 6038, 6048, and 6677, will be helpful. Section 6038 is a statutory mechanism for monitoring the dealings between a United States person and any foreign corporation, foreign partnership, or other
In slight contrast, § 6048 is concerned with monitoring the dealings between a United States person and foreign trusts.
Section 6048(b) also requires anyone who is treated as the owner of a foreign trust under the rules of subpart E of part I of subchapter J of chapter 1 of the Internal Revenue Code (better known as the grantor trust rules of 26 U.S.C. §§ 671-679) (the “Grantor Trust Rules”) to annually submit “such information as the Secretary may prescribe with respect to such trust for such year.”
With this background in mind, we turn to ' the International Penalties at issue here.
a) § 6038 and Failures to File Form 5471
For the reasons explained more fully below, the Court concludes that Sam, Charles, and Dee violated § 6038 by failing to file Forms 5471 with respect to the various IOM corporations and/or Cayman LLCs owned by the Sam International Penalty Trusts and the Charles and Dee International Penalty Trusts. In fact, the Debtors do not seem to dispute the effect of the SDNY Court’s determination that these trusts were Wyly grantor trusts on their respective obligations to have filed Forms 5471 under § 6038.
But, even if they do, an analysis of the relevant statutes and regulations confirms their respective obligations to file Forms 5471 with respect to the foreign corporations the Sam International Penalty Trusts and the Charles and Dee International Penalty Trusts owned (collectively, the “Foreign Corporations”).
Section 6038 defines “[c]ontrol of corporation” for the purpose of Form 5471 filings:
A person is in control of a corporation if such person owns stock possessing more than 50 percent of the total combined voting power of all classes of stock entitled to vote, or more than 50 percent of the total value of shares of all classes of stock, of a corporation— For purposes of this paragraph, the rules prescribed by section 318(a) for determining ownership of stock shall apply.1164
Turning to 26 U.S.C. § 318(a)(2)(B)(ii), we see why the SDNY Court’s grantor trust determinations lead to a finding of control under § 6038. Section 318(a)(2)(B)(ii) states that “[sjtock owned, directly or indirectly, by or for any portion of a trust of which a person is considered the owner under [the Grantor Trust Rules] shall be considered as-owned by such person.”
That leaves only Dee, who is also considered to “control” the Foreign Corporations for the purpose of § 6038. Under 26 U.S.C. § 318(a)(1)(A), “[a]n individual shall be considered as owning the stock owned, directly or indirectly, by or for ... his spouse.”
However, if Dee is considered a grantor of the Charles and Dee International Penalty Trusts, she “controls” the Foreign Corporations through her status as grant- or.
Dee does not argue otherwise. Rather, Dee’s arguments focus solely on her defenses to her liability for the International Penalties — d.e., reasonable cause and excessive fines under the Eighth Amendment. In fact, Debtors’ counsel waived any argument that Dee was not a grantor of the Charles and Dee International Penalty Trusts during closing argument.
Whether the District Court’s finding in SEC v. Wyly that the IOM Trusts are “grantor trusts” applies to years after those in the SEC litigation, ie., 2005-2013, if, as the United State alleges, the Debtors cannot identify material factual or legal changes relating to the IOM Trusts beyond 2004 (the final year addressed in the District Court’s findings)?1174
Debtors’ counsel answered the Court’s question by stating that “... this ties into
Whether Dee has' any grantor tax liability for 2011, 2012, and 2013 since she was never a grantor and they ceased to be grantor trusts on Charles’ death.1177
Debtors’ counsel responded to the Court’s question regarding this contested issue of law by stating “[t]hat’s the one we just talked about,”
Thus, it is clear based on the statements of Dee’s counsel in open court that Dee was no longer attempting to argue that she should not be treated as a grantor of the Charles and Dee International Penalty Trusts. As the Fifth Circuit has. held, “a district judge must be able to winnow the issues for trial. This includes rebanee on statements made by counsel in open court disavowing specific claims.”
For these reasons, the Court concludes that Sam, Charles, and Dee controlled the Foreign Corporations and were required to file Forms 5471 in accordance with 26 U.S.C. § 6038, which they did not do. This means that, absent a viable reasonable cause defense or relief under the Eighth Amendment, the Debtors are liable for International Penalties under § 6038(b) for their respective failures to file Forms 5471.
b) § 6048(b) and Failures to File Form 3520-A
The Court next examines whether the Wylys violated § 6048(b) by failing to file Forms 3520-A regarding the Sam International Penalty Trusts and the Charles
26 U.S.C. § 6048(b) provides that “[i]f, at any time during any taxable year of a United States person, such person is treated as the owner of any portion of a foreign trust under the [Grantor Trust Rules], such person shall submit such information as the Secretary may prescribe.”
Accordingly, under 26 U.S.C. §§ 6048(b) and 6677, Sam, Charles, and Dee are liable for penalties equal to the greater of $10,000 or 5% of the gross value of the Sam International' Penalty Trusts’ assets and the Charles and Dee International Penalty Trusts’ assets, respectively, for each year that they failed to file a Form 3520-A unless they can establish a right to relief under the reasonable cause provisions of § 6677 or the Eighth Amendment.
c.) § 6048(c) and Failures to File Form 3520
(1) In General
The Court now turns to the issue of whether the Debtors violated § 6048(c) by failing to report certain trust distributions, which analysis is more complicated. The IRS asserts that the Debtors are liable for International Penalties because they failed to file Form 3520 when they were required to do so under 26 U.S.C. § 6048(c). As noted above, § 6048(c) requires a Form 3520 to be filed “[i]f any United States person receives (directly or indirectly) during any taxable year of such person any distribution from a foreign trust.”
Here, there are three different types of transactions that the IRS asserts should have been reported as “distributions” on Form 3520 for the purposes of 26 U.S.C. § 6048(c): (i) cértáin annuity payments received by Sam, Charles, and Dee; (ii) offshore funds used to purchase domestic real estate, and (iii) certain loans made to Sam, Charles, and certain Wyly-related entities.
(2) Annuity Payments
The IRS argues that Sam, Charles, and Dee should have reported the annuity payments they received from certain of the Foreign Corporations that had issued annuities to them on Forms 3520. According to the IRS, this is because the Foreign Corporations with the annuity obligations to them are wholly owned by one of the Sam International Penalty Trusts or the Charles and Dee International Penalty Trusts, and that by not reporting the annuity payments Sam, Charles, and Dee violated § 6048(c).
Normally, income received as a result of an annuity transaction entered into between a foreign corporation and a United States taxpayer would not need to be reported on Form 3520 in order to satisfy § 6048(c). This is because such a transaction would not involve a gratuitous transfer from a foreign trust.
Conversely, the Debtors argue that the annuity payments cannot be reportable distributions under the statutory language for three reasons. First, the annuity payments received from the offshore system were not made by trusts, but rather by subsidiary IOM corporations.owned by the applicable trust — ie., one of the Foreign Corporations, and so the payments are not distributions “from a foreign trust” that are reportable under § 6048(c).
Returning to the Debtors’ first argument — ie., that the annuity payments were not made by a foreign trust but were rather made by a wholly owned corporation of a foreign trust — it is fair to say that the IRS and the Debtors read § 6048(c) differently. Pointing to the statute, the IRS notes that it requires reporting “[i]f any United States person receives (directly or. indirectly) ... any distribution from a foreign trust.”
In order to decide which of these two readings of the statute is better, the Court must construe the language of § 6048(c). In 2015, the Fifth Circuit laid out the following “roadmap” for the type of statutory construction in which the Court must now engage:
*560 The starting point in discerning congressional intent is the existing statutory text. When faced with questions of statutory construction, we must first determine whether the statutory text is plain and unambiguous and, if it is, we must apply the statute according to its terms. The parties disagree on whether the plain text of the statute needs to be found ambiguous before a canon of construction, such as ejusdem generis, can be applied.... In any case, there is no doubt that legislative history can only be a guide after the application of canons of construction. Only after application of principles of statutory construction, including the canons of construction, and after a conclusion that the statute is ambiguous may the court turn to the legislative history. For the language to be considered ambiguous, however, it must be susceptible to more than one reasonable interpretation or more than one accepted meaning.1195
As the Fifth Circuit has held, for statutory language to be ambiguous, “it must be susceptible to more than one reasonable interpretation or more than one accepted meaning.”
Moreover, while rules of grammar are helpful in interpreting statutes, “we should not be guided by a single sentence or member of a sentence; rather, we must look to the provisions of the whole law, and to its object and policy.”
With these principles of statutory construction firmly in mind, the Court turns to the text of the statute, which provides:
If any United States person receives (directly or indirectly) during any taxable year of such person any distribution from a foreign trust, such person shall make a return with respect to such trust for such year which includes..,1202
Again, the Debtors argue that the parenthetical phrase “directly or indirectly” modifies only the word “receives” in § 6048(c). The IRS argues that the parenthetical phrase “directly or indirectly” also modifies “from a foreign trust.”
Initially, the Court notes that for the IRS’ interpretation of § 6048(c) to be cor
6048(c) — If any United States person receives (directly or indirectly) during any taxable year of such person any distribution from a foreign trust (directly or indirectly), such person shall make a return with respect to such trust for such year which includes.
The addition of a second “(directly or indirectly)” immediately after “from a foreign trust,” if it appeared in the statute, would unquestionably support the IRS’ interpretation. However, the statute does not contain this additional phrase. The phrase “directly or indirectly” is contained within a parenthetical in only one location in the statute. Placing modifying words within parentheses indicates a limiting or cabin-ing effect. It would be at least somewhat unnatural to read a parenthetical phrase as expansively modifying multiple clauses in a sentence as opposed to only the clause that the parenthetical phrase follows.
Thus, it seems that a plain language reading of § 6048(c) unambiguously favors the Debtors’ interpretation that “directly or indirectly” modifies only “receives” in § 6048(c). However, even if § 6048(c) is “susceptible to more than one reasonable interpretation or more than one accepted meaning” such that we need to apply canons of statutory interpretation, the IRS’ reading is further weakened by application of these canons.
The canon of statutory construction called the last antecedent rule (the “Last Antecedent Rule”) is relevant here. The Last Antecedent Rule is described in the following way by a widely cited treatise on statutory construction:
Referential and qualifying words and phrases, where no contrary intention appears, refer solely to the last antecedent. The last antecedent is the last word, phrase, or clause that can be made an antecedent without impairing the meaning of the sentence. Thus a proviso usually applies to the provision or clause immediately preceding it. A qualifying phrase separated from antecedents by a comma is evidence that the qualifier is supposed to apply to all the antecedents instead of only to the immediately preceding one. As with all the rules of interpretation, the last antecedent rule is merely another aid to discover legislative intent or statutory meaning, and is not inflexible and uniformly binding. In general, then, where the sense of an entire act requires that a qualifying word or phrase apply to several preceding or even succeeding sections, the qualifying word or phrase is not restricted to its immediate antecedent.1205
An illustration of the Last Antecedent Rule in action is helpful. If, in order to get a pilot’s license, a statute requires that an applicant “undergo a physical examination, obtain a passing score on a certification test, and complete forty hours of inflight training within six months prior to submitting an application,” there is an arguable ambiguity. Does “six months prior to submitting an application” modify all of the requirements, or only the in-flight training requirement? According to the Last Antecedent Rule, the answer is that it only modifies the in-flight training requirement. An applicant could obtain a passing score on a certification test eight months prior to submitting an application and still be eligible for a pilot’s license, as long as she completed her forty hours of
Although the Last Antecedent Rule is not absolute, “and can assuredly be overcome by other indicia of meaning,” it is nevertheless widely used.
Achieving the IRS’ reading of § 6048(c) requires us to ignore the Last Antecedent Rule. The Last Antecedent Rule counsels that “directly or indirectly” should modify only the word “receives” in § 6048(c) because this is the antecedent that immediately precedes “directly or indirectly.” In contrast, the IRS wants to read the quali-lying words “directly or indirectly” as modifying a postcedent that appears later on in the statutory text. Such a reading runs counter to the Last Antecedent Rule.
Another principle of statutory construction supports the Debtors’ reading of § 6048(c) — i.e., the canon of resolving ambiguities in tax statutes, and especially tax statutes imposing penalties, in the taxpayers’ favor. As the Supreme Court stated:
In the interpretation of statutes levying taxes it is the established rule not to extend their provisions by implication, beyond the clear import of the language used, or to enlarge their operation so as to embrace matters not specifically pointed out. In case of doubt they are construed most strongly against the government, and in favor to the citizen.1210
This maxim holds particularly true in the context of tax penalties, where the Supreme Court notes “one ‘is not to be subjected to a penalty unless the words of the statute plainly impose it.’”
The IRS’ reading of § 6048(c) violates the canon of resolving ambiguity in tax penalty statutes in favor of the taxpayer and against the government. As the Court indicated in its analysis of the grammatical structure of § 6048(c), the IRS’ reading of the statute is a strained one. Imposing penalties on the Debtors in the face of such a strained reading runs counter to the canon of statutory interpretation that resolves any such ambiguities in the taxpayer’s favor.
Thus, the Court concludes that the Wylys did not violate § 6048(c) by not reporting annuity payments they received from certain of the Foreign Corporations on Form 3520 because these annuity payments were not distributions “from a foreign trust” within the meaning of § 6048(c). But, there is another reason why the annuity payments did not need to be reported on Form 3520 — they were not gratuitous transfers, as explained below.
The Wylys argue that private annuity payments are not reportable distributions under § 6048(c) because they are payments made pursuant to a contract as opposed to gratuitous transfers.
The Court disagrees
The Court agrees with the Debtors’ argument that the annuity payments here were not gratuitous transfers. In exchange for their indirect transfers of options and warrants to one of the Foreign Corporations, Sam, Charles, and Dee received a private annuity of equivalent value, a fact that the IRS did not contest at trial. The annuity obligations are documented in private annuity agreements. The applicable Foreign Corporation was/is contractually obligated to make the annuity payments at issue here. When payments were made to Sam, Charles, and Dee, it was pursuant to those agreements. On this record, there is no basis upon which to conclude that the annuity payments were gratuitous transfers, let alone gratuitous transfers from a foreign trust.
This brings us to the IRS’ last argument — ie., that the application of one of the various judicial doctrines — substance over form, economic substance, or step transaction-can transmute the Wyly annuity payments into a different, reportable type of transaction that is both (i) gratuitous, and (ii) ignores the role of the Foreign Corporations. The Court rejects the IRS’ attempts to apply these doctrines in this context for the reasons explained below.
As the Court has noted in its gift analysis, the IRS has invoked the doctrines of substance over form, economic substance, and step transaction in a haphazard manner. The IRS raised the novel argument that both the annuities and the Foreign Corporations should be disregarded under these doctrines as it relates to the imposition of International Penalties for the first time in posttrial briefing. This is troubling, because the IRS’ post-trial argument that the Foreign Corporations and annuities should be disregarded runs directly counter to positions taken by the IRS in (i) its Proofs of Claim, (ii) the Computation Stipulations, and (iii) statements made by its counsel in open court. For the reasons explained below, the IRS is foreclosed from arguing that either the Foreign Corporations or the annuities should be disregarded under the doctrines of substance over form, economic substance, or step transaction as it relates to the imposition of International Penalties.
After an enormous amount of work by both parties, the IRS and the Debtors entered into the Computation Stipulations, which resolved almost all issues regarding how to calculate the Debtors’ income tax, gift tax, and penalty liability. The Computation- Stipulations resolved the amount that the Debtors would owe to the IRS if this Court determined that they were liable for gift taxes or penalties; and definitively resolved the question of how much income tax the Debtors owe but for a few
The Parties agree that, due to the Memorandum Opinion and Order issued in this Section 505 proceeding (docket numbers 789 and 791) relating to collateral estoppel and the classification of the Isle of Man trusts at issue in this proceeding, the IRS is not pursuing its alternative income tax position set forth in the POC that the IOM entities are shams or its alternative gift tax position that Debtors made gifts during the 1992 and 1996 calendar years. However, should that Memorandum Opinion and Order be reversed or otherwise overturned, the United States reserves its rights to pursue any and all alternative theories in the Debtors’ 505 motions, including but not limited to the tax treatment of the offshore Isle of Man trusts, and any gift tax transactions involving the Isle of Man trusts.1224 [t]he foreign entities (the foreign trusts and the foreign corporations owned by foreign trusts), have been determined to be shams. The income from these sham foreign entities was required to be reported on the Debtor’s individual income tax returns (Form 1040). The character of the um’eported income is ordinary income, short term capital gains and long term capital gains.1228
As the language quoted above indicates, the parties’ Computation Stipulations are based on calculations in the IRS’ Proofs of Claim.
The IRS’ main and alternative theories are mutually exclusive. The main theory, which is embodied in the Computation Stipulations, expressly relies on the existence of the Foreign Corporations to support the existence of Subpart F income. The alternative theory, a theory that the IRS expressly disclaims in the Computation Stipulations, relies on the non-existence of the Foreign Corporations.
Now, in the context of their attempt to recover International Penalties, the IRS argues — without using the word “sham”— that the Foreign Corporations should be disregarded. As the Debtors point out in their own post-trial briefing, in asserting that the Foreign Corporations should be disregarded for the purposes of reporting distributions under § 6048(c), the IRS fails to mention that disregarding these entities would make any § 6038 penalties inapplicable (because there would be no controlled foreign corporations for which the Debtors failed to file Forms 5471) and would result in a much lower income tax
The Court notes that the Fifth Circuit has opined that, as a general rule, “parties entering into stipulations during the course of a judicial proceeding are es-topped to take positions inconsistent therewith.”
On January 6, 2016, the Court was advised by the IRS’ counsel that the IRS had been authorized to enter into the Computation Stipulations by the Associate Attorney General of the United States. While it took the parties time to “tweak” the language of the Computation Stipulations, it was finalized and filed with the Court on January 26.
Now the IRS has raised — for the first time in its post-trial briefing — arguments that the Debtors have failed to report transactions under § 6048(c) that specifically rely on the Court disregarding and/or shamming the Foreign Corporations. The Court does not see how it can disregard and/or sham the Foreign Corporations for International Penalties purposes without doing so for income tax purposes, which cannot be done consistent with the Computation Stipulations. Thus, the Court concludes that the IRS is estopped from arguing that the Foreign Corporations should be disregarded.
The purpose of the economic substance doctrine is to prevent taxpayers “from reaping tax benefits from transactions lacking in economic reality.”
In this regard, the Debtors have already lost the tax benefits of their offshore system by virtue of the SDNY Court’s grant- or trust determinations. Now the IRS wants to go further. The IRS wants to apply the doctrines of substance over form, economic substance, and step transaction in order to make the Debtors liable for reporting penalties — after the proper tax treatment of the Debtors’ transactions has already been determined and in ways that are counter to the IRS’ previous positions. Applying the substance over form, economic substance, or step transaction doctrines solely to create reportable transac
While no longer necessary, in the interests of completeness, the Court will rule on the Wyly’s third argument as to why their annuity payments did not need to be reported on Form 3520 — ie., they did not need to report the annuity payments because those payments were reported on their tax returns as income.
Regardless of whether the Wylys needed to subject their, annuity payments to self-employment tax, § 6048(c)(1)(A) settles the debate as to whether reporting these annuity payments on Form 1040 also satisfied Form 3520 reporting obligations. It did not. Section 6048(c)(1)(A) requires that the name of the trust from which a distribution is received be reported in order to satisfy Form .3520 reporting requirements. This is no mere technicality, as the entire point of § 6048 is to allow the IRS to monitor the movement of funds through offshore trusts, a task that is not
Nevertheless, for the reasons stated above, the Court concludes that the Wylys did not violate § 6048(c) by failing to report annuity payments received from the Wyly offshore system as distributions on Form 3520 because the annuity payments were not: (i) distributions from a foreign trust, or (ii) gratuitous.
(3) Real Estate Transactions
The second category of “distributions” that the IRS argues the Wylys were required to report pursuant to § 6048(c) are real estate transactions indirectly involving one or more of the Sam International Penalty Trusts or the Charles and Dee International Penalty Trusts. Specifically, the IRS argues that Sam should have reported on Form 3520 transfers of offshore funds involving the acquisition of (i) the Cottonwood Ventures I property, (ii) the Cottonwood Ventures II property, and (iii) the Rosemary’s Circle R Ranch property.
were merely investments by subsidiaries of the IOM trusts in U.S. entities that themselves invested in U.S. real estate. In exchange for their investment in the U.S. entities, the IOM subsidiaries received a pro rata interest in those entities. Accordingly, these transactions were simply investments by subsidiaries of the trusts. They were not distributions by the trusts because the trusts did not part with legal title to any trust asset.
The IRS’s inability to articulate a coherent position as to why these real estate transactions constituted gifts further illustrates that they were not reportable transactions. Furthermore, the IRS’s gift theory was that the purported gift was made either to an entity or to a family member of the Debtors. Accordingly, those transactions would not be reportable by the Debtors in any event.1251
The Court largely agrees with the Debtors. From the Court’s perspective, the IRS’ arguments here suffer from the same flaw in statutory construction as did its initial argument regarding the annuity payments that Sam, Charles, and Dee received from one or more of the Foreign Corporations. While it is true
Moreover, the IRS identifies no statutory, regulatory, or case law authorities that would allow the Court to ignore the non-gratuitous nature of the real estate investments that it identifies as distributions reportable under § 6048(c). In exchange for the transfers of offshore funds, the applicable Foreign Corporation received an equivalent ownership interest in the domestic entities that hold legal title to the real estate. Under any circumstance that makes the transfers not gratuitous.
Finally, even if the prior two reasons are incorrect, the IRS seeks to recover from the wrong “recipient.” Sam, Charles, and Dee did not receive the offshore funds. Rather, the applicable domestic entity did; and thus, it is the “United States person” who was obligated to report to the IRS. For all of these reasons, the Court concludes that the Debtors are not liable for violations of § 6048(c) by virtue of not reporting the transfers of offshore funds used to purchase domestic real estate as distributions on Form 3520.
Although the IRS argues that these real estate transactions can be treated as gratuitous distributions directly from the IOM trusts by ignoring (i) the existence of the Foreign Corporations and the domestic entities, and (ii) the non-gratuitous nature of the transfers via application of the doctrine of substance over form, the Court declines to do so here because, as discussed above in the context of the annuity payments: (a) the IRS is estopped from arguing that the Foreign Corporations should be disregarded, and (b) it is inappropriate to apply the doctrines of substance over form, economic substance, or step transaction purely for the purpose of creating a reportable transaction through which penalties can then be extracted from the Wylys.
(4) Security Capital Loans
The last form of “distribution” that the IRS asserts the Wylys were required to report on Form 3520 under § 6048(c) are loans received by Sam, Charles, and certain Wyly-related entities from Security Capital, who obtained the money it loaned out from one or more of the Foreign Corporations. As explained below, there are actually three sets of loans at issue. With respect to each loan, the IRS argues that it should have been reported on Form 3520 as distributions under § 6048(c) both because the text of the statute requires it and because the loans were gratuitous transfers as opposed to true loans under IRS regulations and the doctrine of substance over form.
As just noted, three sets of loans are at issue here. The first set of loans was made to Charles. These loans included a $6,000,000 loan from Security Capital to Charles made in October 2002 and an additional $25,000,000 loan from Security Capital to Charles made in March 2003.
The second set of loans was made to Sam. These loans included a $10,000,000 loan to Sam from Security Capital made in July 2003.
The third set of loans was made to what are characterized by the IRS as various Wyly-related entities. These loans include $11,500,000 loaned from Security Capital to Green Mountain Energy Resources, LLC (“Green Mountain Energy”) in 1998.
The Court rejects the IRS’ argument that these loans are reportable distributions under § 6048(c) for three reasons. First, § 6048(c) does not require a United States person to report a loan that they receive from a foreign grantor trust; it only requires that loans from a foreign non-grantor trust be reported. That makes sense because reporting a loan from a foreign grantor trust would be like reporting a loan to yourself — completely unnecessary. But, further explanation may be helpful. Section 6048(c) does not discuss loan transactions as distributions.
For example, Charles signed a note payable to Security Capital in connection with his $6,000,000 October 2002 loan.
Sam also signed a note payable to Security Capital in connection with his $10,000,000 July 2003 loan.
Moreover, Sam signed a note payable to Security Capital in connection with his $15,000,000 January 2002 loan. This $15,000,000 loan
The evidence in the record — as well as Security Capital’s proofs of claim, of which this Court takes judicial notice — indicates that the loans that Security Capital made to Sam and Charles were in fact treated as loans by all of the parties involved. The IRS has the burden of showing that penalties such as the International Penalties are applicable in the first instance under 26 U.S.C. § 7491(c). In the absence of sufficient evidence that the loans to Sam and Charles were in fact gratuitous transfers, the Court cannot conclude that the Debtors needed to report these loans on Form 3520 under § 6048(c).
Third, as the Court has explained before in the context of its analysis of the annuity payments and the real estate transactions, the IRS misinterprets the language of § 6048(c) to attempt to capture these loans as “distributions” to Sam and Charles “from a foreign trust.” All of the loans at issue here wereToans from Security Capital, a Cayman Islands company setup in order to administer loan transactions made at the Wylys’ direction.
Once again, the IRS argues that, in spite of the Court’s conclusion that the text of § 6048(c) does not require reporting of these loans on Form 3520, these loans were in actuality gratuitous transfers directly from a Sam International Penalty Trust and a Charles and Dee International Penalty Trust to Sam and Charles, respectively. For the reasons explained in the context of analyzing the annuity payments and the real estate transactions, the Court
(5) Sales of Options to IOM Corporations
Finally, the Court must determine whether the Debtors violated § 6048(a) by failing to report the- sale of options to certain of the Foreign Corporations. Section 6048(a)(3)(A)(ii) requires a United States person who transfers money or property to a foreign trust to file a Form 3520 alerting the IRS that one of these events has occurred.
As relevant here, in 1999, Charles sold stock options to Quayle Limited (IOM) and Elegance Limited (IOM) and Sam sold stock options to Greenbriar Limited (IOM) and East Carroll Limited (IOM) (collectively, the “1999 Option Sales”).
The relevant text of 26 U.S.C. § 6048(a)(3)(A)(ii) reads as follows;
The term “reportable event” means ... the transfer of any money or property (directly or indirectly) to a foreign trust by a United States person ...
Notably, the structure of § 6048(a)(3)(A)(ii) mirrors that of § 6048(c). Although in its briefing the IRS does not appear to argue that the 1999 Option Sales are reportable events under the text of § 6048(a)(3)(A)(ii) and instead relies exclusively on the doctrine of substance over form, the Court notes that the same statutory analysis that it applied to § 6048(c) applies here. The 1999 Option Sales were not sales to foreign trusts; rather, they were sales to certain of the Foreign Corporations, which are wholly owned by one of the Sam International Penalty Trusts or the Charles and Dee International Penalty Trusts.
For these reasons, the Debtors are liable for the following: (i) International Penalties under 26 U.S.C. § 6038(b) because
H. Did the Debtors Establish Their Reasonable Cause Defenses to the Imposition of International Penalties?
1. Introduction
Because the Court has concluded that the Debtors are liable for certain of the International Penalties, the Court must now evaluate their respective reasonable cause defenses to this liability. For the reasons explained more fully below, the Court concludes that Sam has not established his reasonable cause defenses by a preponderance of the credible evidence, but that Dee has established her reasonable cause defenses and thus, will not be held liable for the International Penalties.
a) Review of Provisions of § 6038
As just discussed, 26 U.S.C. § 6038(a)(1) requires every United States person who controls a foreign business entity to fíle a Form 5471. Under § 6038(a)(2) and its accompanying regulations, Forms 5471 are due at the same time as the United States person’s tax return.
However, § 6038’s reasonable cause provision may provide the Debtors with an avenue of relief from this liability. Specifically, § 6038(c)(4)(B) provides that “the time prescribed under paragraph (2) of subsection (a) to furnish information ... shall be treated as being not earlier than the last day on which (as shown to the satisfaction of the Secretary) reasonable cause existed for failure to furnish such information.”
b) Review of Provisions of §§ 6048(b) and 6677
As just discussed, § 6048(b) requires every United States person who is treated as the owner of any portion of a foreign trust under the Grantor Trust Rules to submit
However, penalties under § 6677 will not be imposed “on any failure which is shown to be due to reasonable cause and not due to willful neglect.”
2. Reasonable Cause and Lack of Willful Neglect
a) In General
Reasonable cause is determined on a ease-by-case basis, taking into account all of the facts and circumstances.
(b) Facts and circumstances taken into account — (1) In general. The determination of whether a taxpayer acted with reasonable cause and in good faith is made on a case-by-case basis, taking into account all pertinent facts and circumstances. (See paragraph (e) of this section for certain rules relating to a substantial understatement penalty attributable to tax shelter items of corpo*578 rations.) Generally, the most important factor is the extent of the taxpayer’s effort to assess the taxpayer’s proper tax liability. Circumstances that may indicate reasonable cause and good faith include an honest misunderstanding of fact or law that is reasonable in light of all of the facts and circumstances, including the experience, knowledge, and education of the taxpayer. An isolated computational or transcriptional error generally is not inconsistent with reasonable cause and good faith. Reliance on an information return or on the advice of a professional tax advisor or an appraiser does not necessarily demonstrate reasonable cause and good faith. Similarly, reasonable cause and good faith is not necessarily indicated by reliance on facts that, unknown to the taxpayer, are incorrect. Reliance on an information return, professional advice, or other facts, however, constitutes reasonable cause and good faith if, under all the circumstances, such reliance was reasonable and the taxpayer acted in good faith ...
The Court must stress that, as in its analysis of the Debtors’ attempted use of reliance on the advice of counsel to negate fraudulent intent under § 6663 and to establish reasonable cause for avoidance of fraud penalties under § 6664, this regulation is a helpful guide but is not controlling. This is because this regulation does not expressly apply to penalties under §§ 6663, 6038(c)(4)(B), or 6677(d), and— unlike under § 6664 — the Court need not evaluate whether the Debtors here have displayed “good faith” in order to relieve them of liability for International Penalties. Rather, as relevant here, the Debtors need only establish “reasonable cause” under § 6038(c)(4)(B) and both “reasonable cause” and lack of “willful neglect” under § 6677(d).
In the context of establishing reasonable cause for failing to file a return on time, the Supreme Court stated in U.S. v. Boyle
b) Reliance on the Advice of Professionals
The Debtors rely almost exclusively on the fact that they relied on the advice of professionals in order to establish their reasonable cause defenses to their liability for International Penalties. The Court discussed the legal standards relevant to establishing reasonable cause by relying on the advice of tax professionals earlier in this opinion in its discussion of Sam’s attempt to use his purported reliance on the advice of counsel to negate fraudulent intent under § 6663 and to establish reasonable cause for avoidance of fraud penalties under § 6664.
To reiterate, when a professional advises a taxpayer on a matter of tax law, such as whether a liability exists or whether a return must be filed, it is reasonable for the taxpayer to rely on that advice without seeking a second opinion, even if that advice turns out to be wrong.
To establish reasonable cause through reliance on the advice of a tax adviser, the taxpayer must meet the following three-prong test, laid out in Neonatology Assocs., P.A. v. Commissioner,115 T.C. at 98 -99: (1) the adviser was a competent professional who had sufficient expertise to justify reliance, (2) the taxpayer provided necessary and accurate information to the adviser, and (3) the taxpayer relied in good faith on the adviser’s judgment.1334
Before proceeding to analyze whether the Debtors have met their burden of establishing their reasonable cause defenses here, one final set of legal principles must be analyzed. Specifically, can a taxpayer establish his reasonable cause defense based on an “honest difference of opinion?”
c) Honest Difference of Opinion
The Debtors assert what they characterize as a separate reasonable cause argument from their reliance on the advice of professionals argument. Specifically, the Debtors argue that there was an honest difference of opinion as to whether the Sam International Penalty Trusts and the Charles and Dee International Penalty Trusts were non-grantor trusts, and that this honest difference of opinion establishes reasonable cause for the Debtors’ failure to file Forms 3520-A and 5471.
Throughout their Pre-Trial Brief, the Debtors maintain' that reasonable cause can be established when there is an honest difference of opinion on the law.
However, as applied here, this Court sees little, if any, difference between the Debtors’ “honest difference of opinion” argument and their reliance on the advice of counsel argument. Indeed, the Debtors meld the two arguments in their own pleadings. For example, in the Debtors’ Amended Proposed Findings of Fact and Conclusions of Law dedicated to their honest difference of opinion argument, the Debtors ask the Court to find that:
When the law is unsettled or unclear, a belief based on a review of the existing authorities establishes reasonable cause for failure to file a form ... Given the complexity and uncertainty of the law during the years at issue, it was entirely reasonable for the Wylys to rely on their professional advisors and believe their advice that the IOM trusts were indeed not grantor trusts to Sam and Charles and that they had filed all required tax returns and forms.1340
As this proposed finding makes clear, the Debtors’ “honest difference of opinion” argument is identical to their “reliance on the advice of professionals” argument. In fact, the argument has to be the same because there is no evidence in the record that the Debtors had any “honest difference of opinion” about how to interpret the relevant tax law independent of the analy-ses provided to them by their tax advisors. Neither Sam nor Dee ever read any of the legal opinions that form the basis of their reliance on the advice of counsel argument,
This Court’s conclusion that these are not separate bases upon which to establish a reasonable cause defense here is bolstered by examining cases where courts have found that a taxpayer had reasonable cause based on an honest difference of opinion. Generally, the “honest difference of opinion” argument is used by courts to provide relief to taxpayers who did not rely on counsel or other professional advis-ors but made a legal mistake when confronted with a confusing provision of the tax law that they interpreted on their own.
Here, the Wylys did not analyze the law independently. They relied on their advis-ors to analyze the law for them. As such, the Court will treat the Debtors’ “honest difference of opinion” and “reliance on counsel” reasonable cause arguments as one and the same.
d) Application to Both Debtors
In their pre-trial briefing, the Debtors sum up their reasonable cause defenses to International Penalties in this way:
As already described above, the Wylys were continually told by their advisors that the 1992 IOM trusts were non-grantor trusts and that the 1994 and 1995 IOM trusts were grantor trusts to Messrs. King and Cairns, respectively. Consistent with this advice, the Wylys properly filed Forms 3520 for the IOM trusts for the years they created and funded such trusts, and filed the Forms 3520-A (required for grantor trusts owned by a U.S. person) annually for the IOM grantor trusts they created until they were terminated in 1996.
No further Forms 3520 or 3520-A were filed, and no Forms 5471 were filed, because the Wylys’ advisors did not tell them to make any additional filings. Based on the conclusions reached by these advisors regarding the characterization of the trusts and the nature of certain other transactions, no such additional information returns should have been filed.
Furthermore, even after the Wylys were told in 2003 that Morgan Lewis thought there was a risk that the 1992 trusts could be treated as grantor trusts to Sam and Charles, they were not advised of any potential need to.file these forms. Although the IRS continues to focus on the views of Morgan Lewis to support these penalties, Debtors reiterate that (i) other advisors (principally Messrs. Chatzky, Tedder, and French, and Meadows Owens) interpreted the same statutory provisions differently, (ii) Morgan Lewis could not (and did not) point to conclusive authority supporting its views because such authority did not exist, (iii) when the Wylys learned about Morgan Lewis’ contrary views, they began disclosing the issues on their federal income tax returns, and (iv) even after being informed of Morgan Lewis’ concerns, the Debtors were not advised to file these information reports. The contrary views were not resolved until the Disgorgement Opinion was issued in 2014. This is further evidence that the state of the law was unclear.
On their advisors’ counsel, the Wylys properly filed all of the tax forms their advisors told them to file, including Forms 3520 for the IOM trusts they settled and funded, Forms 3520-A each year for the trusts those advisors told them were grantor trusts to them, and other obscure forms when advised to file them, such as FBARs .and Forms 8938.
% ^ * •
At no point during the 22-year period at issue in these Cases were Sam and Charles Wyly ever advised by any of their lawyers they engaged to file the Forms 5471, 3520 or 3520-A at issue. And, furthermore, for the first 12 years of this period (until 2003), the Wylys were not advised that there was even a meaningful risk that the trusts were*584 grantor trusts — the prerequisite finding necessary to trigger the Form 3520-A and 5471 filing requirements.
Moreover, the Debtors rely upon the Supreme Court’s decision in U.S. v. Boyle
The IRS objects to the Debtors’ reasonable cause defenses on multiple grounds; specifically that: (i) Tedder and Chatzky (and at times Meadows Owens’ attorneys) are promoters of the Wyly offshore system on whose advice the Wylys may not rely, (ii) the advice that Sam and Charles was given regarding the offshore system was based on facts that Sam and Charles knew to be false, (iii) the Debtors never actually heard any of the advice on which they purport to rely firsthand, and (iv) the Debtors cannot actually produce any of the advice that was supposedly given to them by Meadows Owens or substantiate what facts were given to Meadows Owens to produce that advice.
In 1991, the memorandum to the Wylys included advice from Tedder stating that (1) Form 3520 must be filed when a foreign trust is formed; (2) attach a copy of the Trust Agreement to the Form 3520 for safety; and (3) file Form 3520-A annually to keep confirming that the Trust is in existence. Tedder specifically advised “Always over disclose to the IRS.” Throughout the time that the Offshore System was operating, the Wy-lys also received additional advice as to these forms. In December 2002, Keeley Hennington, the Wylys agent, acknowledged the Form 3520 filing requirement and awareness of the same. In August 2003, Lubar, another Wyly agent, informed Keeley Hennington and Boucher, two additional Wyly agents, that Form 5471s must be filed. In October 2003, Todd Welty, then with the Meadows firm, also discussed the penalties associated with not filing a Form 3520 and 5471 with Keeley Hennington. While silence of advisors is not sufficient to establish a reasonable cause defense, the record here is clear that the Wylys were actually advised to file these forms and received this advice as early as 1991 in advance of their implementing the Offshore System.
(1) As to Sam
As to Sam, the IRS asserts International Penalties beginning in 1996.
As previously found, Sam never received an opinion that the Bulldog IOM Trust was- a non-grantor trust as to him.
Sam next argues that French told him that the Bulldog IOM Trust was a non-grantor trust. But, there are numerous problems with Sam relying on any tax advice French allegedly gave him, as discussed supra at pp. 501-13. First, French was not competent to give Sam advice regarding the proper legal characterization of the Bulldog IOM Trust as he was a securities, lawyer, not a tax lawyer. That French was not competent to give such advice is demonstrated by the fact that the Wylys hired expert tax lawyers to advise them — ie., Lubar, Owens, Pulman, Chamberlain Hrdlicka, DeCastro West, and arguably Tedder and Chatzky. Further, that Larry Bean, a tax lawyer at French’s law firm (Jackson Walker), reviewed the offshore system as proposed by Tedder early on and advised French that it “might work,” after stating that their firm, Jackson Walker,
As previously found, on May 19, 1993, Sam did receive opinion letters from Ted-der, Chatzky & Berends
As previously found, in 1993 Sam’s trusted advisor and agent, French, sought and received an opinion regarding the proper legal characterization of the 1992 IOM trusts that Sam had settled — ie., Bulldog IOM Trust, Lake Providence IOM Trust, and Delhi IOM Trust. French was concerned about the conclusions reached by Tedder and Chatzky and so French went to an international tax specialist, Lu-bar, for advice on the Wylys’, behalf.
As previously found, Sam turned to Owens for legal advice on tax issues beginning around 1998. However, as previously found, there is no credible evidence in the record that Owens’ firm, Meadows Owens,independently analyzed the proper legal characterization of the Sam International Penalty Trusts until late October 2003.
As discussed above, Sam’s liability for International Penalties flows from the characterization of the Sam International Penalty Trusts as grantor trusts to Sam. For the reasons just explained, Sam failed to prove that he received advice on which he can reasonably rely that characterizes the Sam International Penalty Trusts as non-grantor trusts as to him and his reasonable cause defense fails.
For the sake of completeness, one final argument will be addressed — ie., Sam’s argument that his professionals never advised him to file Forms 3520-A and 5471 and that he relied upon this failure in concluding that he had filed all required forms. As the Debtors’ note in their briefing, the failure of Sam’s professionals to advise him to file Forms 3520-A and 5471 was “[biased on .the conclusions reached by these advisors regarding the characteriza
The Court takes no issue with the Debtors’ contention that an advisor’s failure to mention that a form must be filed can constitute advice that the form does not need to be filed.
What is more, Sam was aware that there were reporting requirements whose applicability depended upon the proper legal characterization of the Wyly offshore trusts as non-grantor trusts as to Sam or as foreign grantor trusts as to King and Cairns. As Sam’s counsel noted, Sam filed Forms 3520-A for offshore trusts that he was advised were grantor trusts as to him — ie., certain of the offshore trusts involved in the 1996 private annuity transactions.
Thus, the evidence shows that Sam was aware — at least to some extent — of the reporting requirements that flowed from his status as a U.S. citizen grantor of foreign trusts. More importantly, Sam was aware that all of the advice he was given about tax consequences and reporting requirements regarding the Wyly offshore system depended on the fact that he was not the grantor of the Sam International Penalty Trusts. And, for the reasons discussed above and in the Court’s analysis of Sam’s reasonable cause defense to the imposition of fraud penalties, Sam had no advice on which he could reasonably rely that established this crucial fact. For all of these reasons, Sam has not established his reasonable cause defense under either § 6088(c)(4)(B) or § 6677(d).
Although Sam’s lack of reasonable cause is enough to make him liable for International Penalties under both §§ 6038(c)(4)(B) and 6677(d), the Court also finds that Sam displayed willful neglect in failing to file Forms 3520-A and 5471 in relation to the Foreign Corporations. Sam’s failure to file these forms was due to “a conscious, intentional failure or reckless indifference.”
As with Sam’s tax fraud, there is little direct evidence that .Sam intentionally failed to file Forms 3520-A and 5471. This is unsurprising. It would be unrealistic to expect Sam — in a Perry Mason moment — to confess that he knew all along that he needed to file these forms but did not. The evidence does show, however, that Sam was aware that the decisions he was making regarding the offshore system were not based on a foundation of uniform, reliable tax advice. For the reasons explained below, this fact, among others, establishes that Sam’s decisions to not file Forms 3520-A and 5471 regarding the Foreign Corporations for over two decades was a product of at least reckless indifference.
. Sam was aware from the outset of his offshore system that the tax positions he was taking regarding the 1992 IOM trusts and the annuity transactions he undertook through them were aggressive.
Sam testified at trial that he hired tax professionals because he realized that the United States tax laws were complicated, and that he needed experts to assist him in complying with those laws, going so far as to testify 'that he was not competent to even read his own tax returns due to their complexity.
The Court agrees that Sam should not be charged with the responsibility to independently evaluate the correctness of the tax advice he received. Moreover, the Court does not expect Sam to be competent to determine which of his expert
So, what did Sam do when he learned in 1993 that his expert advisers disagreed over the proper legal characterization of the 1992 IOM trusts and the tax consequences flowing from the annuity transactions undertaken through them? Similarly, what did Sam do knowing that the factual predicate underlying Lubar’s advice regarding the characterization of the Bessie IOM Trust and the La Fourche IOM Trusts as grantor trusts as to King and Cairns, respectively, was wrong?
In short; Sam did nothing. He simply-ignored their disagreement and the factual lies upon which the 1994 and 1995 IOM trusts were predicated and proceeded to undertake more annuity and other business transactions through the Sam International Penalty Trusts for the next decade until his hand was forced by a chance encounter that Boucher had with Lubar in the Cayman Islands in 2003. At that time Boucher learned of Lubar’s 1993 advice to Sam’s agent, French,
Specifically, Boucher and Hennington, also acting as Sam’s agents, met with Lu-bar in London (just as French had done literally a decade earlier) and, after understanding Lubar’s earlier concerns, Boucher and Hennington prepared a written memorandum addressed to their principal, Sam (among others), disclosing what they had learned.
And, as previously found, after a failed anonymous meeting with the IRS to try to resolve the Wyljfs looming tax problems that Lubar undertook on Sam’s and Charles’ behalf in August 2003, Henning-
So, once again, the question must be asked — what did Sam do to resolve the •legal uncertainty and clarify his reporting obligations? The answer this time is slightly different but, as relevant here, the difference is not meaningful. While Sam did nothing to attempt to resolve the legal uncertainty, he did start filing Forms 8275 with the IRS disclosing the possibility that the IOM trusts were grantor trusts as to him, that there were possible funding issues with the 1994 and 1995 trusts, and that property had been exchanged with subsidiaries of these foreign trusts in exchange for private annuities.
And, in early 2004, the IRS began its audit of Sam, the focal point of which was Sam’s offshore system and the transactions undertaken offshore as Hennington testified.
But, again, what did Sam actually do? Nothing of real consequence — he simply waited for the IRS to come after him, all the while continuing his offshore activities. Such a caviler attitude towards his reporting obligations for 20 plus years reflects, at a minimum, reckless indifference. For these reasons, the Court concludes that Sam acted with willful neglect when he failed to file Forms 3520-A and 5471.
(2) As to Dee
Since the Court found that Dee is not liable for fraud penalties under § 6663, the Court has not previously examined Dee’s reasonable cause defenses. Like Sam, Dee attempts to establish her reasonable cause and lack of ■willful neglect by her purported reliance on the advice of professionals. According to Dee, her reasonable cause defense boils down to this:
Dee Wyly reasonably relied on her husband to handle the' couple’s financial, tax, and legal affairs. Dee Wyly never had any reason to suspect that Charles Wyly ever engaged in illegal or fraudulent activity, and there is no evidence that he ever did. Dee Wyly had no reason to suspect that the legal, financial, and tax professionals retained by her husband provided anything other than competent professional advice and counsel.1397
Under 26 C.F.R. § 1.6664-4 (which the Court acknowledges is not controlling here but is nevertheless helpful), advice “is any communication, including the opinion of a professional tax advisor, setting forth the analysis or conclusion of a person, other than the taxpayer, provided to (or for the benefit of) the taxpayer and on which the taxpayer relies, directly or indirectly.”
However, if Dee is to rely on professionals through her reliance on Charles, then there is an argument that her reliance can only establish reasonable cause to the same extent as Charles’ reliance could. This is important, because, like Sam, any reasonable cause defense asserted by Charles (or more accurately, by his probate estate) would fail here for the same reasons Sam’s reasonable cause defenses failed. A brief reminder is appropriate. Although the names of Charles’ offshore trusts and corporations were different than Sam’s, and he established fewer offshore trusts and corporations than Sam, Charles’ actions and the advice he received is identical, in all material respects, to that of Sam. In short, the two brothers implemented a substantively identical system of offshore trusts and corporations in the IOM through which they undertook substantively identical transactions from 1992 through 2011 when Charles died. Thus, for the reasons just explained as to Sam, Charles would not be able to prove that he received advice on which he can reasonably rely that characterizes the Charles and Dee International Penalty Trusts as non-grantor trusts as to him. And, for the same reasons that Sam’s reasonable cause defenses to the imposition of International Penalties failed, any such defenses asserted by Charles (or his probate estate) would also fail.
Despite the problems Charles (or his probate estate) would have establishing a reasonable cause defense here, the case of Reset v. C.I.R.
The taxpayers in Reset were a husband (“Don”) and wife (“Rebecca”), both of whom were highly educated and had obtained their law degrees.
Tax issues arose when Don attempted to claim losses related to DRPC on his tax return.
The IRS also sought to recover various penalties from Don and Rebecca related to the overstated losses stemming from the Frost Bank loans.
Stewart Goodson, the certified public accountant who prepared the returns here, testified that John Gwaltney, DRPC’s accountant, told him to treat loans listed on the financial statements as coming from the bank as loans from [Don], and that such loans were in fact from [Don]. Mr. Goodson, an agent of DRPC, thus treated the loans as loans from [Don], In light of our finding that there was no separate loan from [Don] to [DRPC], we find that [Don’s] reliance on Mr. Good-son was not reasonable, as based on inaccurate information that Mr. Goodson made no effort to verify, and that appears to have been furnished to him on [Don’s] instructions.
Apparently not eager to be held liable for tax penalties because of a dubious tax position taken by her husband, Rebecca also attempted to obtain penalty relief based on the innocent spouse defense.
Petitioner wife, an attorney, signed the 1987 tax return. She undoubtedly noticed that the losses attributable to her husband’s corporation would act to shelter her income. Given the ’ circumstances, we find that a reasonably prudent taxpayer should have known that the tax liability stated was erroneous, or that further investigation was warrant*596 ed. We find that petitioner wife should have investigated whether the losses were properly deductible.
Since we hold that petitioner wife should have known, or was on reasonable notice, that the loss was improper, we must conclude that she does not qualify for treatment as an innocent spouse under section 6013(e).
Thus, the tax court held that Rebecca was liable for both tax and penalties because her husband claimed erroneous deductions on their joint tax return.
Rebecca, but not Don, appealed the tax court’s decision to the Fifth Circuit.
The relevant factors that we are to consider indicate that [Rebecca] did not know and did not have reason to know that the deductions in question would give rise to a substantial understatement on the 1987 joint return. First, [Rebecca’s] education, albeit advanced, provided her with no special knowledge of complex tax issues such as basis computation. She had a background in history and practiced personal injury law. Second, [Rebecca] was not personally involved with DRPC’s business and financial affairs to any significant degree; rather, she was engaged full-time in her law practice and was the family’s sole source of financial support. In addition, she gave birth to their second child in 1987. Third, the record is devoid of evidence of lavish or unusual expenditures compared to the Resers’ normal standard of living and spending patterns, which exhibits no notable changes during the years in question. To the contrary, they invested most of [Rebecca’s] income into DRPC and consumed the rest on the family’s living expenses. In addition, they incurred substantial debt when borrowing money to invest in DRPC. And ultimately, the Resers divorced, and Don filed for bankruptcy. Finally, [Rebecca] cannot be penalized for Don’s discredited efforts to recast the Frost Bank loan in a tax-favorable light. Indeéd, [Rebecca] was not even aware of the second set of “promissory notes” until 1991, several years after she had signed the 1987 joint return.
The Fifth Circuit also noted that the ultimate conclusion that these losses were not deductible by Don and Rebecca rested on the application of “an extremely difficult and technical process” that had been hotly contested and on which IRS agents had reached two different conclusions.
Had [Rebecca] asked Don, [or the accountants] about the deductions, they would have told her what they believed-that DRPC’s losses were properly deductible in full. Neither the court nor the law will penalize [Rebecca] for failing to perform the hollow act of asking questions, the answers to which would have provided no new or different information.
On this basis, the Fifth Circuit found that the tax court had been clearly erroneous in finding that Rebecca was not an innocent spouse.
However, there were certain penalties for which Rebecca did not qualify for innocent spouse relief based on a technicality, namely that the tax liability from which she sought relief was not a high enough amount.
The relevant inquiry for the imposition of a negligence penalty is whether the taxpayer acted reasonably in claiming the loss. The Tax Court found that [Rebecca’s] reliance on Stewart Good-son, the CPA who prepared the 1988 joint' return, was not reasonable, as based on inaccurate information, in light of its decision that there was no separate loan from Don to DRPC. We find clear error in this conclusion of the Tax Court. For the same reasons that we concluded that [Rebecca] did not have reason to know of the substantial understatement on the 1987 joint return, we conclude that she acted reasonably in relying on the professionals who prepared the 1988 joint return. In fact, but for her failure to meet a technical requirement, she would have been an innocent spouse for purposes of the 1988 joint return. Goodson and Bryan, two CPA’s at a national accounting firm, both agreed that the Resers’ basis in DRPC was sufficient to claim the losses as deductions. As we stated in Chamberlain v. Commissioner, “[t]o require the taxpayer to challenge the [expert], to seek a ‘second opinion,’ or try to monitor [the expert] on the provisions of the Code himself would nullify the very purpose of seeking the advice of a presumed expert in the first place.” Furthermore, [Rebecca] was wholly unaware of Don’s belated attempt to recast the Frost Bank loan to his tax advantage.
The Fifth Circuit then considered whether, in addition to not being negligent, Rebecca had established that she had acted with reasonable cause and good faith.
We have just concluded that [Rebecca] acted reasonably in relying on the professionals who prepared the 1988 joint return and would have been an innocent spouse for purposes of that return but for her failure to meet a technical requirement ... we exonerate her from liability for this penalty. Any other con-*598 elusion would be absurdly inconsistent with our earlier holdings.
In this way, Rebecca escaped all liability for taxes or penalties related to erroneous deductions taken by her husband on their joint return.
Thus, in Reset, the Fifth Circuit stated that it would be “absurdly inconsistent” to hold that an innocent spouse who had no actual knowledge or reason to know of a tax liability caused by her husband’s actions did not also have reasonable cause in relation to penalties caused by those same actions. The Fifth Circuit reached this conclusion in part on the basis that a spouse who did not know that the professional advice she relied on was based on incorrect facts provided by her husband could still rely on that advice, especially when that advice was regarding complicated tax law. There was no indication in the Fifth Circuit’s reasoning that it was important whether Rebecca relied on this advice on her own or “through her husband,” and the court’s admonition against punishing Rebecca based on the hollow act of asking Don or the accountants questions would be inconsistent with a need for direct reliance. If Rebecca had been relying on advice directly, she would not have needed to ask questions, because she would have known the advice’s contents already.
Finally, the Fifth Circuit held that Rebecca had acted with reasonable cause despite the fact that she was a highly educated lawyer who was at least somewhat involved in her husband’s financial affairs.
There are numerous similarities between Dee’s situation here and Rebecca’s situation in Reset. Like Rebecca, Dee has been found to be an innocent spouse with respect to their income tax underpayments because she did not know or have reason to know of the income coming in from the offshore system.
The evidence shows that even to this day Dee is completely unaware of the intricacies of the offshore system Charles established.
Just as Rebecca in Reser was unaware that her husband had mischaracterized the nature of the DRPC loans to his professionals in seeking their advice, Dee was unaware (i) of the specifics of the advice that Charles had received, (ii) whether the advice actually addressed the relevant factual and legal issues that needed to be addressed, (iii) what factual assumptions served as the predicate for the advice, and (iv) whether there was anything wrong with the advice that was given to her husband by the many professionals that were consulted on his behalf regarding the offshore system. Although Charles is charged with knowledge of the contents of the advice that he received, albeit mostly indirectly through French, Robertson, Hennington and Boucher, and Charles is also charged with the knowledge that there were missing legal opinions, conflicting legal opinions, and legal opinions based on false factual assumptions that all impacted the tax status of the offshore system and his obligation to file reports about it with the IRS, Dee had no way of knowing any of that. In fact, had Dee sought out this information regarding the offshore system she — even more so than Rebecca in Reser — would in all likelihood have been told that nothing was amiss. Sam has consistently proclaimed his innocence of any wrongdoing here because, according to him, every professional he consulted told him all was fine with the offshore system. There is no reason to believe that Charles would have said anything different. And, while the Court has not found Sam’s testimony credible given its review of the actual advice on which Sam purports to rely, Dee would have had no way of knowing that reassurances from Sam and Charles, if given, were untrue.
The Fifth Circuit refused to penalize Rebecca in Reser “for failing to perform the hollow act of asking questions, the answers to which would have provided no new or different information,” especially when she had no knowledge that Don had falsely told their accountants that he had
Dee’s case is also similar to Rebecea’s in Reser in that Dee is not entitled to innocent spouse relief for International Penalties due to a technicality. The technicality in Reser was that, at that time, only tax liabilities greater than 25% of the adjusted gross income for the preadjustment year were eligible for innocent spouse relief.
While the legal and factual issues are not identical, the similarity of Dee’s situation to that of Rebecca in Reser strongly suggests that the Fifth Circuit would conclude that Dee acted with reasonable cause and not with willful neglect for the purposes of §§ 6038(c)(4)(B) and 6677(d). As the Fifth Circuit noted, it would be absurdly inconsistent to hold that Dee is an innocent spouse for the purposes of Charles’ and her income tax underpayments but that she is not able to establish reasonable cause for the purposes of avoiding liability for the International Penalties, which flow from the same legal characterization of the Charles and Dee International Penalty Trusts as grantor trusts.
At trial, Dee credibly testified that, after Charles’ death, she continued to rely on the Wyly family office to prepare her tax returns and to handle her finances, and that she has never had any reason to suspect that they were deficient in their duties.
In light of all of these facts and the legal principles articulated in Reser, the Court holds that Dee has established that she acted with reasonable cause and without willful neglect for all of the tax years at issue. Thus, Dee has established her reasonable cause defenses with respect to her liability for the International Penalties.
In coming to its conclusion as stated above, this Court has reviewed the cases
Mr. Molever always prepared joint Federal income tax returns for himself and [Mrs. Molever], and [Mrs. Molever] relied on him, as an accountant, to do it properly. If she questioned anything he did, he thundered at her and accused her of ignorance. He assured her that he was in frequent consultation with two certified public accountants in Phoenix. In fact, Mr. Molever was deducting the expenses of his litigation as business expenses, assuring petitioner that he had “loss carryforwards.” Among these expenses he deducted 40 percent of the Molevers’ living expenses (rent, electricity, water, and telephone). Mr, Molever insisted that petitioner file a Form W-4 for 1987 on which she claimed 10 dependency exemptions. For 1988, petitioner filed a Form W-4 claiming 2 exemptions. Mr. Molever became enraged when he learned of this, and insisted petitioner again claim 10 exemptions for 1989. When correspondence or calls from the IRS arrived, petitioner directed them to Mr. Molever and relied on him to handle all tax matters.
* * *
In early 1988, Mr. Molever was very ill with cancer and emphysema. After the episode in which he threatened petitioner with a gun, Mr. Molever’s doctor advised petitioner that shortage of oxygen to his brain could explain his irrational episodes. Eventually, he required oxygen full-time. On April 10,1991, Mr. Molever died.
Even in this situation, involving a wife faced with an irrational and violent husband who actively resisted her attempts to do what was right under the Internal Revenue Code, the tax court held that the taxpayer was negligent for not filing her tax return on time, and that reliance on her husband was insufficient to establish reasonable cause.
Dee’s situation is distinguishable from the above cases in an important respect.
For all of these reasons, the Court concludes that Dee has established her reasonable cause defenses to her liability for the International Penalties under 26 U.S.C. §§ 6038(c)(4)(B) and 6677(d). ■
I. Does the Imposition of the International Penalties Violate the Eighth Amendment?
1. Applicable Supreme Court Precedent
The Debtors final argument to avoid liability for the International Penalties is that those penalties constitute excessive fines under the Eighth Amendment of the United States Constitution, which provides, as relevant here, that: “[e]xcessive bail shall not be required, nor excessive fines imposed, nor cruel and unusual punishments inflicted.”
In contrast, while the IRS does not dispute the importance of these four Supreme Court decisions, it argues that under their holdings: (i) the International Penalties are not “fines” as that term is defined for purposes of the Excessive Fines Clause, and (ii) even if the International Penalties are “fines,” they are not excessive. The
For the reasons explained below, the Court largely agrees with the IRS and concludes that the International Penalties are not fines. Alternatively, the Court concludes that if the International Penalties are properly construed as fines, they (i) are not excessive as applied to Sam, and (ii) are excessive as applied to Dee.
a) The Supreme Court Decisions
The Debtors rely upon U.S, v. Halper,
Thus, the Halper Court addressed the question of “whether a civil sanction, in application, may be so divorced from any remedial goal that it constitutes ‘punishment’ for the purposes of double jeopardy analysis.”
It is important to stress that Habper is a double jeopardy case, and that a later Supreme Court case — Hudson v. U.S. — “in large part disavowed] the method of analysis used in United States v. Halper” in the double jeopardy context and called the. Halper framework “ill considered” and “unworkable.”
The second case relied upon by the Debtors here is Browning-Ferris Indus. of Vt., Inc. v. Kelco Disposal, Inc.,
The Debtors next rely upon Austin v. U.S.,
The Excessive Fines Clause limits the government’s power to extract payments, whether in cash or in kind, “as punishment for some offense.” [Browning-Ferris,492 U.S. at 265 , 109 S.Ct-2909.] (emphasis added). “The notion of punishment, as we commonly understand it, cuts across the division between the civil and the criminal law.” United States v. Halper,490 U.S. 435 , 447-448,109 S.Ct. 1892 , 1901,104 L.Ed.2d 487 (1989). “It is commonly understood that civil proceedings may advance punitive as well as remedial goals, and, conversely, that both punitive and remedial goals may be served by criminal penalties.” Id., at 447,109 S.Ct., at 1901 . See also United States ex rel. Marcus v. Hess,317 U.S. 537 , 554,63 S.Ct. 379 , 389,87 L.Ed. 443 (1943) (Frankfurter, J,, concurring). Thus, the question is not, as the United States would have it, whether forfeiture under §§ 881(a)(4) and (a)(7) is civil or criminal, but rather whether it is punishment.
In considering this question, we are mindful of the fact that sanctions frequently serve more than one purpose. We need not exclude the possibility that a forfeiture serves remedial purposes to conclude that it is subject to the limitations of the Excessive Fines Clause. We, however, must determine that it can only be explained as serving in part to punish. We said in Halper that “a civil sanction that cannot fairly be said solely to serve a remedial purpose, but rather can only be explained as also serving either retributive or deterrent purposes, is punishment, as we have come to understand the term.”490 U.S., at 448 ,109 S.Ct., at 1902 .
The Austin Court noted that the determination of whether a sanction was a punishment and therefore a fine under the Excessive Fines Clause was governed by Halper: “[u]nder [Halper], the question is whether forfeiture serves in part to punish, and one need not exclude the possibility that forfeiture serves other purposes to reach that conclusion.”
In Halper, we focused on whether “the sanction as applied in the individual case serves the goals of punishment.”490 U.S., at 448 ,109 S.Ct., at 1902 . In this case, however, it makes sense to focus on §§ 881(a)(4) and (a)(7) as a whole. Halper involved a small, fixed-penalty provision, which “in the ordinary case ... can be said to do no more than make the Government whole.” Id., at 449,109 S.Ct,, at 1902. The value of the conveyances and real property forfeitable under §§ 881(a)(4) and (a)(7), on the other hand, can vary so dramatically that any relationship between the Government’s actual costs and the amount of the sanction is merely coincidental. See Ward,448 U.S., at 254 ,100 S.Ct., at 2644 . Furthermore, as we have seen, forfeiture statutes historically have been understood as serving not simply remedial goals but also those of punishment and deterrence. Finally, it appears to make little practical difference whether the Excessive Fines Clause applies to all forfeitures under §§ 881(a)(4) and (a)(7) or only to those that cannot be characterized as purely remedial. The Clause prohibits only the imposition of “excessive” fines, and a fine that serves purely remedial purposes cannot be considered “excessive” in any event.
The Austin Court did not articulate a test for determining whether a particular forfeiture or other type of punishment is excessive under the Excessive Fines Clause. Instead, it held only that payments to a sovereign that are made as punishment for some offense are subject to the limitations of the Excessive Fines Clause, and that a sanction is punishment under the Excessive Fines Clause if it serves a retributive or deterrent purpose.
Finally, the Debtors rely upon U.S. v. Bajakajian.
The Bajakajian Court adopted the Austin Court’s analysis, and stated that “[f]or-feitures — payments in' kind — are thus ‘fines’ if they constitute punishment for an offense.”
Applying this standard, the Supreme Court held that the forfeiture imposed on Bajakajian was grossly disproportional to the gravity of his offense, and thus violated the Excessive Fines Clause because
Respondent’s crime was solely a reporting offense. It was permissible to transport the currency out of the country so long as he reported it. Section 982(a)(1) orders currency to be forfeited for a “willful” violation of the reporting requirement. Thus, the essence of respondent’s crime is a willful failure to report the removal of currency from the United States. Furthermore, as the District Court found, respondent’s viola*608 tion was unrelated to any other illegal activities. The money was the proceeds of legal activity and was to be used to repay a lawful debt. Whatever his other vices, respondent does not fit into the class of persons for whom the statute was principally designed: He is not a money launderer, a drug trafficker, or a tax evader ... And under the Sentencing Guidelines, the maximum sentence that could have been- imposed on respondent was six months, while the maximum fine was $5,000.
# $
The harm that respondent caused was also minimal. Failure to report his currency affected only one party, the Government, and in a relatively minor way. There was no fraud on the United States, and respondent caused no loss to the public fisc. Had his crime gone undetected, the Government would have been deprived only of the information that $357,144 had left the country.
# # *5»
Comparing the gravity of respondent’s crime with the $357,144 forfeiture the Government seeks, we conclude that such a forfeiture would be grossly disproportional to the gravity of his offense. It is larger than the $5,000 fine imposed by the District Court by many orders of magnitude, and it bears no articulable correlation to any injury suffered by the Government.
Thus, these cases — beginning with Halper and ending with Bajaka-jian — lay out a framework for how to
apply the Excessive Fines Clause. In sum, to be constrained by the Excessive Fines Clause, a sanction must be (i) a fine, and (ii) excessive.
b) Lower Courts’ Interpretations of Supreme Court Precedent
The most recent of the Supreme Court cases just discussed, Bajakajian, was decided over fifteen years ago. Since Baja-kajian was decided, lower courts have had ample opportunity to apply its holdings to monetary sanctions. Significantly, neither party has cited a case to the Court, nor has the Court been able to locate one through its own research, invalidating a non-forfeiture, legislative civil penalty under the Excessive Fines Clause.
2. Are the International Penalties “Fines”?
Various courts of appeals have categorically refused to extend Austin and Bajakajian into the realm of civil tax penalties. For example, in McNichols v. C.I.R.,
Using Austin as a springboard, petitioner argues that the additions to the income tax were punitive, and that, by seizing his property and then subjecting that same property to an income tax along with penalties and interest, the IRS has violated the proportionality requirements of the Eighth Amendment. We decline to take the giant leap that petitioner urges for several reasons. First there is an insurmountable wall of tax cases, discussed infra, holding that the government.has a right to do precisely what it has done here. Second, the instant case is a civil income tax not a forfeiture case as was Austin. And Austin does not directly or impliedly suggest that either its holding or statements to the effect that a forfeiture can be an excessive fíne under the Eighth Amendment are or should be applicable to any actions other than forfeitures under 21 U.S.C. §§ 881(a)(4) and (a)(7). Nor, under the facts of this case, do we perceive any reason for applying the principles of Austin to petitioner. Petitioner agreed to the forfeiture. He stipulated to the tax court that he derived unreported taxable income in 1981 and 1982 from the sale of marijuana. The plea agreement warned petitioner that income tax might be due. Indeed, prior to signing the plea agreement, petitioner was sent a notice of deficiency assessing*610 taxes and penalties for the years 1981 and 1982. The Supreme Court in James v. United States,366 U.S. 213 ,81 S.Ct. 1052 ,6 L.Ed.2d 246 (1961) made an observation that applies to petitioner:
We should not continue to confound confusion, particularly when the result would be to perpetuate the injustice of relieving embezzlers of the duty of paying income taxes on the money they enrich themselves with through theft while honest people pay their taxes on every conceivable type of income.
Id. at 221,81 S.Ct. at 1056 . We find no Eighth Amendment violations.
As is obvious from its decision, the First Circuit refused to read the Austin Court’s definition of “fines” as encompassing civil tax penalties. The McNichols court also rejected an attempt to use Halper for the purpose of characterizing civil tax penalties as fines, stating that “[t]o use Halper as a base for vaulting into the tax arena would be to misapply the case and distort its holding.”
The remedial character of sanctions imposing additions to a tax has been made clear by this Court ... They are provided primarily as a safeguard for the protection of the revenue and to reimburse the Government for the heavy expense of investigation and the loss resulting from the taxpayer’s fraud.
Holding that Helvering v. Mitchell was “the foundation stone” for “the wall of cases” that barred McNichols’ Excessive Fines Clause defense, the First Circuit concluded that the Helvering Court’s characterization of civil tax penalties as remedial meant that civil tax penalties are not fines, and that because they are not fines they are not subject to the Excessive Fines Clause’s limitations.
While the Fifth Circuit has not spoken as directly as some of the other circuits on the issue of whether civil tax penalties can ever be “fines” under Austin, decisions of the Fifth Circuit that touch upon this issue also counsel against a holding that the International Penalties are fines. For example, in the context of a double jeopardy analysis, the Fifth Circuit noted that a civil penalty for failure to file an information return “is analogous to the fraud penalty at issue in Helvering,” and for that reason found the civil penalty for failure to file an information return to be remedial rather than punitive for double jeopardy purposes.
As relevant here then, under Austin, a monetary sanction is a “fine” if it is “payment to a sovereign as punishment for some offense,”
The Congress was informed that certain U.S. settlors established foreign trusts, including grantor trusts, in tax haven jurisdictions. Income from such foreign grantor trusts was taxable on a current basis to the U.S. grantor, but the Congress understood that there was noncompliance in this regard. The Congress was concerned that the prior-law civil penalties for failure to comply with the reporting requirements applicable to foreign trusts established by U.S. persons had proven to be ineffective. In order to deter noncompliance, the Congress believed that it is appropriate to expand the reporting requirements relating to activities of foreign trusts with U.S. grantors or U.S. beneficiaries and to increase the civil penalties applicable to a failure to comply with such reporting requirements.1513
The “prior-law civil penalties” that the Joint Committee on Taxation described had been limited to a maximum of $1,000.
The explanation of the Joint Committee on Taxation cited above indicates that the International Penalties are aimed at preventing — or deterring — the precise actions that the Wylys have engaged in here — i.e., surreptitious transactions by U.S. taxpayers with foreign trusts on whose income tax should have been paid, and whose existence and taxability went undetected for many years, in part because reporting requirements were not followed. The International Penalties represent more than housekeeping requirements. As the IRS notes, the International Penalties “are connected to tax evasion.”
Under Austin, this deterrence factor weighs in favor of holding that the International Penalties have at least some punishment purpose, and are therefore fines that can be limited by the Excessive Fines Clause. However, there are also numerous factors that weigh against such a holding. Even the Austin Court noted — citing Halper — that in the ordinary case a small, fixed-penalty provision “can be said to do no more than make the government whole” and that such penalties are therefore remedial.
The parties have not cited, nor has the Court located through its own research, a single case that holds that a tax penalty such as the International Penalties is a fine under the Excessive Fines Clause, let alone an excessive fine. As discussed above, most circuit courts that have considered the question of whether it is appropriate to treat tax penalties as fines under the Excessive Fines Clause have answered that question with a categorical “no,” and the tax court has followed suit. The one circuit court that has left the door open to even the possibility of a tax penalty being treated as a fine under the Excessive Fines Clause has stated that such penalties could only be fines where “no remedial purpose” was served or where such penalties are “several times greater than necessary to achieve a remedial purpose.”
Such a strong consensus among the circuit courts — as well as the tax court — that Austin and Bajakajian should not be extended into the tax realm counsels against
From this Court’s perspective, a holding that the International Penalties are not fines is consistent with relevant Supreme Court precedent, including Austin and Ba-jakajian. First, both of those eases were decided within the narrow context of forfeitures related to crimes, and extending their holdings to the realm of civil tax penalties would be, as the First Circuit said, a “giant leap.”
Second, when the Supreme Court disavowed the reasoning of Halper in Hudson v. U.S., it observed that “all civil penalties have some deterrent effect.”
In sum, those courts that have been faced with the dilemma of how to apply an Excessive Fines Clause analysis to civil tax penalties have all arrived at largely the same answer — i.e., civil tax penalties such as the International Penalties are not fines, and therefore the Excessive Fines Clause is not applicable to them. This Court likewise concludes that the International Penalties are not fines, adopting the reasoning of those courts.
Alternatively, even if this Court concluded that the International Penalties are fines, lower court cases interpreting Baja-kajian make strong arguments that fines such as the International Penalties under § 6677 can almost never be excessive. In Bajakajian, the Supreme Court held that in order to determine if a forfeiture is excessive, a court must: “compare the amount of the forfeiture to the gravity of the defendant’s offense. If the amount of the forfeiture is grossly disproportional to the gravity of the defendant’s offense, it is unconstitutional.”
Even assuming arguendo that the Excessive Fines Clause is implicated in this case, there is no basis for concluding that the $44,068 sanction is excessive. If the addition to tax is always calculated as fifty percent of the tax deficiency regardless of the means by which the income is accrued, the sanction could not be excessive as to one person, but not excessive as to another. All persons forced to pay additions to tax for civil fraud are treated in the same manner.
Moreover, the tax court agreed with the Thomas court’s observation in a post-Ucyo-kajian context in Gorra v. C.I.R.,
There is also a strong argument that a fixed-penalty provision such as the $10,000 fine assessed under § 6038 should rarely be considered excessive. The Supreme Court in Halper noted that “the Government is entitled to rough remedial justice, that is, it may demand compensation according to somewhat imprecise formulas, such as reasonable liquidated damages or a fixed sum plus double damages” without such a sanction being labeled as punishment.
Another factor counseling against declaring the International Penalties excessive here is that even in the realm of forfeitures — where offenders may be punished with a total surrender of property on top of the maximum statutory fine — courts have been reluctant to find that those forfeitures are “grossly disproportional.” For example, in US. v. Wallace,
The Eleventh Circuit explained the rationale for this conclusion in U.S. v. 817 N.E. 29th Drive, Wilton Manors, Fla.,
Translating the gravity of a crime into monetary terms — such that it can be proportioned to the value of forfeited property — is not a simple task. Fortunately for us, this task has already been performed by two very competent bodies. The first is Congress, which, in enacting criminal laws, has specified the maximum permissible fine for a given offense. Because Congress is a representative body, its pronouncements regarding the appropriate range of fines for a crime represent the collective opinion of the American people as to what is and is not excessive. Given that exces-siveness is a highly subjective judgment, the courts should be hesitant to substitute their opinion for that of the people. Consequently, if the value of forfeited property is within the range of fines prescribed by Congress, a strong presumption arises that the forfeiture is constitutional.
The Eleventh Circuit also noted in Wilton Manors that “[i]t is important to remember that the Excessive Fines Clause was drafted in an era in which the amount of a fine was determined solely by the judiciary; the Clause was thus intended as a limitation on courts, not legislatures.”
Here, the International Penalties represent the very maximum fine that the Fifth Circuit would use as a benchmark for assessing proportionality. Moreover, the Fifth Circuit in Wallace also noted that the pilot’s violation was more serious than the one at issue in Bajakajian, as it was a continuing violation occurring over the course of seven years as opposed to a onetime violation.
Both Wallace and an additional Fifth Circuit case — Newell Recycling Co., Inc. v. U.S. E.P.A.
a) As to Sam
With these standards in mind, we turn to the International Penalties at issue here. According to the Computation Stipulations, Sam owes $427,614,822 in International Penalties related to failures to file Forms 3520-A and 5471,
First, it is important to note that the International Penalties are an inherently different type of penalty than the forfeitures at issue in Austin and Bajakajian. Unlike fixed penalty provisions such as the International Penalties, “forfeiture of property is a penalty that has absolutely no correlation to any damages sustained by society or to the cost of enforcing the law.”
Here, that disconnect is lacking. Section 6677(b) penalizes United States persons who are treated as owners of foreign trusts under the Grantor Trust Rules.
What is more, many courts — including the Fifth Circuit — have held that a forfeiture that involves property of a value that falls within the maximum statutory fíne that could be imposed for the same offense is strongly presumed to be constitutional.
An assessment of the Bajakajian factors also leads the Court to the conclusion that the International Penalties are not grossly disproportional as to Sam. The first Bajakajian factor — the essence of the violator’s wrongdoing and its relation to other illegal activity
Just as Sam avoided SEC reporting requirements by structuring the securities held in the offshore system so that no single entity held a reportable amount of stock in order to avoid an SEC position that was inconsistent with his tax position, Sam avoided filing Forms 3520-A and 5471 in order to conceal the extent of the Wyly offshore system and to avoid an IRS audit.
The second Bajakajian factor — whether the violator fits into the class of persons for whom the statute was principally designed
The third Bajakajian factor — the nature of the harm caused by the violator’s conduct
While interesting, Sam’s argument lacks force. First, Sam has no one to blame but himself for the enormous amount of International Penalties he is liable for. As early as 1993, Sam’s trusted agent, French, was made aware that there was a signifi
Second, the harm caused by Sam’s reporting violations should not be measured merely against the amount of Sam’s tax liability. Sam should have paid the taxes he owes without the need for a lengthy audit and a multi-year federal court proceeding. Moreover, Sam had the use of the $121 million of income taxes he owed for the period that he failed to pay his tax obligation. Obviously, the ongoing harm of Sam’s reporting violations — in addition to the base amount of taxes owed — is compounded by: (i) the time value of money lost by the government, (ii) the significant costs incurred by the government in pursuing Sam, (iii) the general blow to the integrity of the tax system caused by Sam’s conduct, and (iv) the risk of collection the government now faces given the passage of time and the dissipation of Sam’s assets. While the penalties assessed against Sam are vast, so too is the harm that he caused. Thus, the third Bajakajian factor weighs against a finding that the International Penalties are grossly disproportional to the gravity of Sam’s offense.
The final Bajakajian factor — the maximum non-forfeiture sentence and fine that could have been imposed
At such time as the gross reportable amount with respect to any failure can be determined by the Secretary, any subsequent penalty imposed under this subsection with respect to such failure shall be reduced as necessary to assure that the aggregate amount of such penalties do not exceed the gross reportable amount (and to the extent that such aggregate amount already exceeds the gross reportable amount the Secretary shall refund such excess to the taxpayer).
For the purposes of Sam’s violations of § 6048(b), “gross reportable amount” is defined as “the gross value of the portion of the trust’s assets at the close of the year treated as owned by the United States person.”
For all of these reasons, even if the International Penalties are fines, they are not excessive fines as applied to Sam.
b) As to Dee
According to the Computation Stipulations, Dee owes $277,312,325 in International Penalties related to failures to file Forms 3520-A and 5471.
In assessing whether the International Penalties are grossly disproportional to the gravity of Dee’s violation, the Court is guided by the Second Circuit’s decision in van Hofe v. U.S.
This series of events came about because Harold had engaged in a relatively small-time marijuana cultivation operation in the couple’s basement.
Mrs. von Hofe’s offensive conduct boils down to her joint ownership of 32 Medley Lane and silence in the face of her husband’s decision to grow marijuana in their basement almost thirty years into their marriage. And yet she is being punished as if she were distributing drugs, when the district court concluded as a matter of fact that she had no knowledge of any distribution or remuneration. The government cannot justify forfeiture of Mrs. von Hofe’s interest in 32 Medley Lane, for the punishment bears no reasonable correlation either to her minimal culpability or any harm she caused.
The Second Circuit reached the opposite conclusion regarding Harold, holding that “Mr. von Hofe’s lengthy and extensive involvement in the manufacture and distribution of marijuana from his basement, the seriousness of his offenses and their relationship to his other criminal activity, allow us to easily conclude that forfeiture of his one-half interest in 32 Medley Lane is not an excessive fine.”
The key takeaway that this Court draws from von Hofe is the need to apply the Bajakajian factors in view of each offender’s particular involvement in the relevant offense. For example, in assessing the harm factor against Dee, it is the harm caused by Dee, not the harm caused by the reporting failure in the abstract that is relevant. With this in mind,' the Court applies the Bajakajian factors to Dee.
The first Bajakajian factor — the essence of the violator’s wrongdoing and its relation to other illegal activity
The second Bajakajian factor — whether the violator fits into the class of persons for whom the statute was principally designed
The third Bajakajian factor — the nature of the harm caused by the violator’s conduct
The final Bajakajian factor — the maximum non-forfeiture sentence and fine that could have been imposed against. Dee, does weigh against a holding that the International Penalties are grossly disproportional to the gravity of Dee’s offense. As with Sam, the International Penalties are the relevant, non-forfeiture fines that can be imposed against Dee.
After assessing the Bajakajian factors as they apply to Dee, this Court concludes that the International Penalties — both under §§ 6038 and 6677 — are excessive fines as to Dee. In spite of its general concerns about finding a percentage-based or flat fine (such as the International Penalties) excessive, the Court cannot ignore the extent to which the Bajakajian factors favor Dee. Of course, one last reminder, this conclusion that the International Penalties as applied to Dee are excessive fines under the Eighth Amendment is an alternative conclusion to an alternative conclusion. The Court’s primary conclusions are that: (i) Dee is not liable for International Penalties because she established her reasonable cause defenses, and (ii) the International Penalties are not “fines” under the Excessive Fines Clause. The Court’s conclusion that the International Penalties are excessive as to Dee is only reached if one or both of its other conclusions are held to be in error.
1. Does Laches Apply Here?
The Debtors argue that those IRS claims that are not barred by a statute of limitations should be barred by laches. Laches is an equitable defense,
While the Debtors state that the Fifth Circuit’s decision in Sage v. U.S.
Even if all of the IRS’ claims here were not subject to an express statute of limitation, Fifth Circuit precedent has also clearly established that the doctrine of laches may not be invoked by taxpayers in order to prevent the IRS from collecting taxes or penalties. In discussing whether a debtor in bankruptcy could invoke the doctrine of laches in order to prevent the IRS from collecting taxes and penalties, the Fifth Circuit stated in In re Fein:
We need not reach the substantive issue of whether the circumstances of this case are appropriate for the invocation of laches, as laches “may not be asserted against the United States when it is acting in its sovereign capacity to enforce a public right or protect the public interest.” See United States v. Popovich,820 F.2d 134 , 136 (5th Cir.), cert. denied,484 U.S. 976 ,108 S.Ct. 487 ,98 L.Ed.2d 485 (1987). The timeliness of government claims is governed by the statute of limitations enacted by Congress. See United States v. Summerlin,310 U.S. 414 , 416,60 S.Ct. 1019 , 1020,84 L.Ed. 1283 (1940); Chevron, U.S.A., Inc. v. United States,705 F.2d 1487 , 1491 (9th Cir.1983). Fein admits that the government timely asserted the federal tax liabilities.
The Fifth Circuit has relied upon this well-known rule in multiple situations where the United States sought to collect outstanding tax deficiencies.
It is beyond dispute that the United States is enforcing its own rights when it seeks to collect taxes and penalties, as it is doing here. As the Seventh Circuit noted in U.S. v. Administrative Enterprises, Inc.,
Since the doctrine of laches may not be used in order to bar the United States from collecting taxes, the Debtors’ defense of laches cannot succeed.
Alternatively, even if the doctrine of laches was applicable here, the Debtors have failed in their proof. Under Fifth Circuit precedent, “[t]o establish that a cause of action is barred by laches, the defendant must show (1) a delay in asserting the right or claim; (2) that the delay was not excusable; and (3) that there was undue prejudice to the defendant.”
The [IRS] claims are extremely late; they were filed a dozen years after attorney Charles Lubar met on behalf of the Wylys with senior IRS officials in Washington in August 2003, in which meeting the IRS advised that it was going to appoint a “champion” to address and resolve all offshore-related issues not only with the IOM trusts related to the Wylys but also any other similarly situated taxpayers’ trusts, and after the Wylys had first included Form 8275 in their annual tax returns. The claims come eleven years after the IRS commenced audits of Charles and Sam’s 2000 returns in early 2004, and nine years after a Senate investigation made public the same facts on which the IRS relies; and four years after a key witness, Charles Wyly, died. The delay is not excusable and it has prejudiced the Debtors, subjecting the IRS Proofs of Claim, not to limitations, but to the defense of equitable laches; and the Debtors so assert.1606
Putting aside for the moment the fact that the Debtors lump together all of the tax years for which the IRS has filed a Proof of Claim as if the delay alleged was equal for all of the years at issue (which it is not), the Debtors have presented no evidence that an eleven-year period between the commencement of an audit and the filing of a proof of claim constitutes an
This same complexity makes the IRS’ delay — if in fact it has delayed — excusable. The Cases involve dozens of offshore entities that engaged in a myriad of complicated financial transactions that were designed — by the Wylys and their sophisticated advisors — to be difficult to unravel.
Finally, the Debtors have failed to show that the IRS’ supposedly inexcusable delay has unduly prejudiced them. Although the Debtors allege that Charles was a key witness, they fail to point to any additional facts or insights that Charles would have provided here that Sam or Evan was not capable of providing. The evidence presented at trial shows that Sam and Charles largely moved in lockstep with respect to their respective offshore systems and the transactions undertaken through them. In fact, from the mountain of evidence presented at trial, it appears to this Court that Sam was the instigator of moving Wyly wealth offshore and that Charles simply followed in his brother’s footsteps. In short, the Debtors’ failed to offer any evidence to support their argument that Charles’ passing has unduly prejudiced them. If anything, Charles’ passing may have strengthened Dee’s other defenses, as there is no witness available to question her testimony about what Charles and she discussed throughout their marriage.
For all of these reasons, the Debtors’ defense of laches fails.
2. Does Estoppel Apply Here?
The Debtors also assert that estoppel should bar the IRS’ claim(s) again them. Estoppel is an equitable doctrine, and it may be invoked in order to avoid injustice in a particular case.
(1) affirmative misconduct by the government, (2) that the government was aware of the relevant facts and (3) intended its act or omission to be acted upon, (4) that the party seeking estoppel had no knowledge of the relevant facts and (5) reasonably relied on the government’s conduct and as a result of his reliance, suffered substantial injury.1610
There are strong policy reasons underlying courts’ reluctance to apply equitable estoppel against the government. As the Supreme Court has pointed out:
When the Government is unable to enforce the law because the conduct of its agents has given rise to an estoppel, the interest of the citizenry as a whole in obedience to the rule of law is undermined. It is for this reason that it is well settled that the Government may not be estopped on the same terms as any other litigant.1614
In terms of when it might be appropriate to apply equitable estoppel against the government, the Fifth Circuit and the Supreme Court agree that “estoppel might be appropriate when the public interest in ensuring that the Government can enforce the law free from estoppel is outweighed by the countervailing interest of citizens in some minimum standard of decency, hon- or, and reliability in their dealings with their Government.”
Here, the Debtors have failed in their proof. Specifically, the Debtors have not proven the first element of their estop-pel defense against the government — ie., that the IRS engaged in any affirmative misconduct. The Debtors allege that es-toppel should apply here for largely the same reasons that they believe that laches should apply — because of “the IRS’s failure to act during its interminable auditing process.”
The only conduct that the Debtors’ arguably point to that could potentially qualify as an affirmative misrepresentation or affirmative concealment by the IRS is that allegedly. “the IRS advised that it was going to appoint a ‘champion’ to address and resolve all offshore-related issues not only with the IOM trusts related to the Wylys but also any other similarly situated taxpayers’ trusts.”
Furthermore, a rebuttal witness called by the IRS who attended the anonymous meeting in August 2003, Danielle Grimm (“Grimm”), specifically denied that it was ever represented at that meeting that an issue champion would be appointed.
Moreover, it is also important to remember that cases on equitable estoppel against the government generally state that the government can only be bound by the acts or statements of its agents that are within the scope of those agents’ authority.
appointed to resolve the Wylys’ tax issues, the IRS could not be estopped by such a statement if that promise was not within the scope of those IRS lawyers’ authority. As Grimm testified, and as the notes from the meeting indicate, no one present at the meeting had the authority to appoint an issue champion.
In Fredericks, the taxpayer (“Freder-icks”) filed a form consenting to an unlimited extension of the statute of limitations for the assessment of taxes.
Moreover, in Fredericks, the IRS used silence for the specific purpose of creating a misapprehension of the facts in the mind of the taxpayer.
Here, however, there is simply no evidence that the IRS intended to cause the Wylys to take any action one way or the other as a result of its lawyers’ alleged representations at the August 2003 meeting or due to the time it took to conduct its audit of Sam’s and Charles’ tax returns. In the first place, there is no evidence that the IRS knew at the time of the August 2003 meeting with Lubar that it was speaking with a Wyly representative.
Similarly, there is no evidence that the fifth element of estoppel — that the Debtors reasonably relied on the government’s conduct and as a result of their reliance, suffered substantial injury — is satisfied here. This is because there is no evidence that the Wylys’ actions were influenced in any way by the IRS’ conduct at the August 2003 meeting or over the course of the audit. The basic structure of the offshore system has not changed since its inception. The idea that Sam and Charles — who are/ were incredibly sophisticated businessmen and who have/had the advantage of incredibly sophisticated counsel — could reasonably rely on the fact that the IRS indicated it might appoint an issue champion and that the IRS had begun auditing the offshore system to continue on their present course without change defies common sense. If anything, these facts — which so clearly indicated that the IRS thought there was something amiss with the offshore system — should have caused Sam and Charles to consider unravelling the offshore system or at least start reporting based upon the potential that the reporting was required. Had Sam and Charles taken this step, much of the sting of the IRS’ so-called delay would be removed, as almost ten years’ worth of taxes, fraud penalties, and International Penalties would not be in dispute today. As the Supreme Court has pointed out: “the party claiming the estoppel must have relied on its adversary’s conduct in such a manner as to change his position for the worse[,] and
The Debtors have also not proven the second and fourth elements of estoppel. The second element of estoppel is that the government was aware of the relevant facts and the fourth element of estoppel is that that the party seeking estoppel had no knowledge of the relevant facts.
Because the Debtors have not satisfied any of the elements necessary for the Court to invoke the rare remedy of estop-ping the government, the Court rejects the Debtors’ estoppel defense.
3. Does the Court have Discretion to Alter the Penalty Amounts?
Although the Joint Pre-Trial Order filed by the parties indicates that one of the issues to be resolved is “[wjhether the Bankruptcy Court has discretion regarding the assessment or amounts of any penalty sought by the IRS,” this issue does not appear to be discussed in any of the Debtors’ briefing or in their proposed findings of fact and conclusions of law.
For these reasons, the Court has no discretion to modify the penalties Congress imposed by statute on the Wylys in these Cases.
K. Suspension of Interest Under 26 U.S.C. § 6404(g)
The Debtors also argue that they are entitled to mandatory interest suspension for tax years 1998 through 2010
(g) Suspension of interest and certain penalties where Secretary fails to contact taxpayer.—
(1) Suspension.—
(A) In general. — In the case of an individual who files a return of tax imposed by subtitle A for a taxable year on or before the due date for the return (including extensions), if the Secretary does not provide a notice to the.taxpayer specifically stating the taxpayer’s liability and'the basis for the liability before the close of the 36-month period[1649 ] beginning on the later of—
(i) the date on which the return is filed; or
(ii) the due date of the return without regard to extensions,
the Secretary shall suspend the imposition of any interest, penalty, addition to tax, or additional amount with respect to any failure relating to the return which is computed by reference to the period of time the failure continues to exist and which is properly allocable to the suspension period.
(B) Separate application. — This paragraph shall be applied separately with respect to each item or adjustment. If, after the return for a taxable year is filed, the taxpayer provides to the Secretary 1 or more signed written documents showing that the taxpayer owes an additional amount of tax for the taxable year, clause (i) shall be applied by substituting the date the last of the documents was provided for the date on which the return is filed.
According to the Debtors: (i) both Sam and Dee timely filed their 1998 through 2010 tax returns, as stipulated by the parties,
1. This Court has Jurisdiction to Determine the Amount of Interest Payable by the Debtors, Including Whether the Debtors Are Entitled to Mandatory Interest Suspension under 26 U.S.C. § 6404(g)
Before turning to the IRS’ argument that this Court lacks jurisdiction, it is helpful to understand the process involved when a taxpayer believes he is entitled to interest suspension under 26 U.S.C. § 6404(g). As explained in Revenue Procedure 2005-38:
taxpayers may notify the Service that interest was assessed in violation of section 6404(g) by submitting Form 843, “Claim for Refund and Request for Abatement.” Taxpayers should write “Section 6404(g) Notification” at the top of the Form 843. The Service will review the Form 843 notification, decide whether to abate interest under section 6404(a), and notify the taxpayer of its decision. Because section 6404(g) is an interest suspension provision, rather than an interest abatement provision, and because section 6404(b) generally bars claims for abatement with respect to income tax, the notification to the taxpayer of the Service’s abatement determination does not constitute a final determination letter from which the taxpayer can petition the Tax Court under section 6404(h).[1657 ]
If the Service does not exercise its authority under section 6404(a) to abate interest alleged to have been assessed in violation of section 6404(g), the taxpayer may pay the disputed interest assessment, file an administrative claim for refund and, if that claim is denied or not acted upon within six months from the date of filing, bring suit for refund under section 7422 and 28 U.S.C. § 1346(a)(1).
Returning to the statute, 26 U.S.C. § 6404(h) provides that:
[t]he Tax Court shall have jurisdiction over any action brought by a taxpayer who meets the requirements referred to*637 in section 7430(c)(4) (A) (ii) [providing net worth limitations] to determine whether the Secretary’s failure to abate interest under this section was an abuse of discretion, and may order an abatement, if such action is brought within 180 days after the date of the mailing of the Secretary’s final determination not to abate such interest.
The Supreme Court interpreted 26 U.S.C. § 6404(h) in the case of Hinck v. U.S.,
[Section 6404(h)] is a precisely drawn, detailed statute that, in a single sentence, provides a forum for adjudication, a limited class of potential plaintiffs, a statute of limitations, a standard of review, and authorization for judicial relief. And Congress enacted this provision against a backdrop of decisions uniformly rejecting the possibility of any review for taxpayers wishing to challenge the Secretary’s § 6404(e)(l)[1659 ] determination. Therefore, despite Congress’s failure explicitly to define the Tax Court’s jurisdiction as exclusive, we think it quite plain that the terms of § 6404(h) — a precisely drawn, detailed statute filling a perceived hole in the law — control all requests for review of § 6404(e)(1) determinations. Those terms include the forum for adjudication.
In Corbalis v. C.I.R.,
According to the IRS, the reasoning in Hinck and Corbalis applies equally here, leaving the tax court with exclusive jurisdiction to consider the Debtors’ claims for interest abatement under § 6404(g). As explained below, this Court disagrees.
Notably, both Hinck and Corbalis are procedurally distinct from the Cases. There, the taxpayers requested abatement or suspension, and the IRS issued a final
Instead, from this Court’s perspective, the relevant statute is 11 U.S.C. § 505(a), which states in relevant part:
(a)(1) Except as provided in paragraph (2) of this subsection, the court may determine the amount or legality of any tax, any fine or penalty relating to a tax, or any addition to tax, whether or not previously assessed, whether or not paid, and whether or not contested before and adjudicated by a judicial or administrative tribunal of competent jurisdiction.
(2) The court may not so determine—
(A) the amount or legality of a tax, fine, penalty, or addition to tax if such amount or legality was contested before and adjudicated by a judicial or administrative tribunal of competent jurisdiction before the commencement of the case under this title[.]
As explained by the Fifth Circuit in In re Luongo,
2. Mandatory Suspension of Interest Does Not Apply in Any Case Involving Fraud, Precluding Suspension for Sam in the Relevant Years
As set forth in 26 U.S.C. § 6404(g)(2)(B), interest suspension shall not apply to “any interest, penalty, addition to tax, or additional amount in a case involving fraud.” As explained by the Code of Federal Regulations,
does not apply to any interest, penalty, addition to tax, or additional amount for a year involving a false or fraudulent return. If a taxpayer files a fraudulent return for a particular year, paragraph (a) [suspension] of this section may apply to any other tax year of the taxpayer that does not involve fraud. Fraud affecting a particular item on a return precludes paragraph (a) of this section*639 from applying to any other items on that return.
Although few courts have addressed the meaning of “fraud” in relation to § 6404(g), those addressing it have interpreted the term consistent with its use in other portions of the statute:
The dispute underlying this motion is whether Sala’s return is a “case involving fraud” under § 6404(g). While no court has addressed fraud under this statute, it is well established that the Government must prove fraud in other parts of the tax code by clear and convincing evidence. Upshaw’s Estate v. C.I.R.,416 F.2d 737 , 741 (7th Cir.1969); Hebrank v. C.I.R.,81 T.C. 640 , 642,1983 WL 14880 (1983); Petzoldt v. C.I.R.,92 T.C. 661 , 699,1989 WL 27845 (1989). I conclude that the Government’s burden of proof under 6404(g) is also clear and convincing evidence.
Thus, to the extent that this Court has found fraud in existence for any given tax year, interest suspension under § 6404(g) is not available for any item on the return.
With respect to Sam, the Court has found fraud in each of tax years 1998 through 2010, the years for which Sam claims to be entitled to interest suspension under § 6404(g).
3. Interest Suspension is Moot as to Dee Because She Did Not Commit Tax Fraud and She is Entitled to Innocent Spouse Relief from the Income Tax Underpayments to Which § 6404(g) Interest Suspension Would Apply
Section 6404(g) states that “[i]n the case of an individual who files a return of tax imposed by subtitle A [titled “Income Tax”] ... the Secretary shall suspend the imposition of any interest, penalty, addition to tax, or additional amount with respect to any failure relating to the return which is computed by reference to the [relevant time period].” On its face, § 6404(g) applies only to income tax-related interest, penalties, additions to tax, or additional amounts. And, as previously found, Dee did not commit fraud
Y. CONCLUSION
Although there were numerous other issues to be addressed (as is obvious from our over 400-page opinion), the heart of the Motions largely boiled down to the Court answering two questions. First, did Sam and Charles commit tax fraud?
And, as noted at the outset of this opinion, the parties’ respective views on how these questions should be answered varied widely. The Court acknowledged at the outset of this opinion that its responsibility was to thoughtfully evaluate the evidence and the parties’ legal arguments in order to come to its own determination of what happened.
After (i) three weeks of trial, (ii) days spent reading designated portions of deposition testimony or trial testimony from the SEC Action of eleven (11) witnesses who did not offer live testimony here,
The Wylys’ version of the truth is simply too glib. We received all this tax advice from a myriad of capable professionals, so we cannot have committed tax fraud. Now, we didn’t read any of the advice ourselves, or hear most of the advice directly, but what we were told about the advice by French, Robertson, Boucher, and Hennington was enough to make our hearts pure.
But, to accept the Wylys’ explanation requires the Court to be satisfied that it is appropriate for extraordinarily wealthy individuals to hire middlemen to do their bidding in order to insulate themselves from wrong-doing so that, when the fraud is ultimately, exposed, they have plausible deniability. To put a finer point on it— here is the Court’s version of what happened, which it has come to after much thought and analysis.
Sam likes what Tedder has to sell in 1991 — a scheme to put hundreds of millions of dollars of wealth offshore in exchange for unsecured private annuities that will only be taxed — at ordinary income rates — when Sam actually receives annuity payments years in the future. So Sam tells his chief outside lawyer, French, who is not a tax lawyer (French is a securities lawyer), to make it happen from a legal perspective, while telling the chief financial officer of the Wyly family office, Robertson, to make it happen from an administrative perspective.
So, it happens — Sam settles the Bulldog IOM Trust with $100 in early 1992 and then enters into six extremely complicated private annuity transactions in February 1992 involving six newly created domestic corporations and six newly created IOM corporations, all of which are owned, directly or indirectly, by Bulldog IOM Trust. Why so many entities to do the private annuity transactions in 1992? Simple — the options Sam assigned to the Nevada corpo
No tax is paid when these annuity transactions are undertaken. Why? Because Sam received — although he never read — written legal opinions from the lawyer who promoted the scheme to him that there would be no tax consequences ’ to him at the time of implementation. However, a key predicate for that legal advice was that the Bulldog IOM Trust had to be a valid foreign non-grantor trust. And, while that’s certainly what the trust formation documents say, surprisingly, in the one hundred formal written legal opinions Sam received over the years concerning the offshore system (including for the 1992 annuity transactions), he never received a written legal opinion stating that the Bulldog IOM Trust was a valid foreign non-grantor trust — from the promoter or anyone else — until 2003, when he got conflicting advice from two different tax professionals Hennington hired on his behalf — Lubar (in mid-2003) and Pulman (in late October 2003), both pieces of advice relayed to him by Hennington, about the characterization of the Bulldog IOM Trust as a grantor or non-grantor trust — Lubar opining that it was a foreign grantor trust as to Sam and Pulman opining that Sam had a “reportable position” that it was not. Of course, simple math tells us that this advice was received over twenty-one years after the Bulldog IOM Trust was established and began conducting business offshore tax-free. But we get ahead of ourselves in the Court’s version of what happened here.
Returning to the 1990s, Sam’s trusted securities lawyer, French, has lingering concerns about the tax consequences flowing from the 1992 annuity transactions, so French goes to London in 1993 to meet' with an extremely well-credentialed international tax lawyer, Lubar, to get a second opinion concerning the status of the Bulldog IOM Trust as a foreign non-grantor trust and the tax consequences flowing from Sam’s 1992 private annuity transactions. French learns that Lubar has concluded that there is a “significant risk” that the Bulldog IOM Trust (and two other similar trusts established in late 1992) will be characterized as foreign grantor trusts to Sam, which dramatically changes the tax consequences flowing from Sam’s 1992 private annuity transactions and any other business transaction undertaken through the Bulldog IOM Trust along with Sam’s reporting obligations.
Although Sam- never directly testified he did not know about the fact that French got this advice from Lubar in 1993, we are asked to conclude that Sam did not know about this advice because the IRS failed to prove that Sam knew about it. In fact, Sam wants us to believe that he did not even know that French went to see Lubar to get a second opinion (again because the IRS failed to prove that he did), although the Court reasonably infers from the trial record that Lubar did not work for free, but instead billed the Wylys for his advice and that the Wyly family office paid those bills.
Given Lubar’s conclusions about the offshore structure used in 1992, French asks Lubar about an alternate structure that might work better and Lubar advises that a foreign grantor trust settled by an individual who is a nonresident alien of the United States could be a better device through which to accomplish the Wylys’ goals. In February 1994, Lubar issues a
French apparently told Sam about at least part of this advice from Lubar, because an individual residing in the IOM who Sam barely knew, King, settled a trust in February 1994 naming Sam and his family members as beneficiaries.
Then, in 1995, another purported foreign grantor trust — La Fourche IOM Trust — is settled,
I wanted to take this opportunity to let you know what a pleasure it has been knowing you over the past years and*643 dealing with you on both business and social matters. I appreciate your many courtesies. As you know, I have established a trust with Wychwood Trust Limited, called The La Fourche Trust, for the benefit of you and your family, and have provided this trust with the sum of $25,000.00. This is to show my gratitude for your loyalty to our mutual ventures and your personal support and friendship. I hope that, wisely managed, this trust fund can grow for many years and inure to the benefit of many generations of your family.
All of this is a lie, except that the La Fourche IOM Trust was established with Wychwood Trust Limited.
The Court has no idea why Buchanan would ask a friend of his to lie for the Wylys, wealthy Americans Cairns had never laid eyes on, although it is likely explained by the fact that Buchanan continued to serve as a trustee of the Bessie IOM Trust through 1998,
Although the Deed of Settlement for the La Fourche IOM Trust states that Cairns settled the trust with $25,000, that too was a lie. And, once the La Fourche IOM Trust was purportedly “settled,” Sam starts transacting business through it offshore including undertaking another complicated private annuity transaction in 1996.
Once again, Sam wants to rely on Lu-bar’s advice as contained in the February 15, 1994 memorandum addressed to French for the tax consequences flowing from transactions undertaken by him through the La Fourche IOM Trust — i.e., no tax (or other reporting) is due because Cairns is not subject to tax or reporting in the United States, but Sam denies knowing the predicate factual assumptions upon which that favorable advice depended— ie., that Cairns had known Sam for a considerable period of time, that Cairns established the La Fourche IOM Trust as < an entirely gratuitous act, and that Cairns would not benefit from his settling of the trust, all of which were untrue.
From this Court’s perspective, Sam cannot have the good without taking the bad. Sam never actually read any of the legal opinions or memoranda he received in connection with the offshore system and that he claims his reliance upon defeats his fraudulent intent or proves his reasonable cause and good faith defense; nor was he required to do so, as he can receive advice indirectly under the tax regulation at issue. Moreover, Sam rarely dealt directly with a lawyer, choosing again to deal with them through middlemen — ie., French, Robertson, Hennington, and Boucher, which the tax regulation also permits. But it is hard to believe that those middlemen chose to only tell Sam about the favorable aspects of the advice they were given on his behalf by the tax professionals they hired on his behalf. We certainly know Hennington and Boucher didn’t, as reflected by what happened in 2003 when Boucher had a chance meeting with Lubar in the Cayman Islands, which led to Hen-nington’s and Boucher’s discovery of many disconcerting facts about the Wyly offshore system and the tax consequences of the transactions undertaken through the offshore system, all of which were reported to Sam, among others, in writing, in detail, immediately.
That Sam may have only heard what he wanted to hear from some of those middlemen — i.e„ the favorable aspects of the advice upon which he purports to rely here— is certainly possible, but the Court rejects the argument that he never knew or understood the assumptions upon which that favorable advice depended. In short, Sam cannot rely on the favorable portions of the professional’s advice he sought, while feigning ignorance of the factual predicates upon which that advice relied for its accuracy. For example, did Sam not wonder why King and Cairns, one individual he barely knew and the other who he did not know at all, each settled a trust with $25,000 in the IOM and named him and his wife and children as beneficiaries? Perhaps that happens all the time in Sam’s life, but if it happened in mine, I would be asking questions — lots of them.
Sam is a sophisticated and well-educated businessman that accumulated great wealth through his business acumen and hard work. And, while he may be an “idea guy” that leaves the day-to-day business details to professional managers and advis-ors he hires, it is clear that he expects results and is knowledgeable about the results they obtain on his behalf. He does not simply turn his wealth over to others and wish them luck. As relevant here, the Court is convinced Sam knew what was happening in connection with the offshore system and that no money or assets moved within that system without Sam’s knowledge and express direction. Let me be clear, that Sam’s directions to the offshore trustees was usually done through the formality of Sam making his “wishes.” known to them — directly or through the trust protectors he appointed — is of little conse
The Court does not believe that the law permits Sam to hide behind others and claim not to have known what was going on around him. This Court has taken its responsibility to sift through the mountains of evidence presented here seriously; it had the benefit of seeing the witnesses and evaluating their credibility and it spent countless hours.reviewing the documents introduced into evidence, including those that were created to attempt to shield Sam from the fraud that the Court is convinced — by clear and convincing evidence — occurred here.
At the same time, the Court is equally convinced that Dee is innocent of any wrongdoing. That she did not know the details of what Sam and Charles had done offshore is clear. And, there was nothing that should have “tipped her off’ that something was amiss. She did not commit fraud, she did not participate in any fraud, she was not willfully blind, and she is entitled to the benefit of the innocent spouse defense.
Orders reflecting these rulings shall be entered separately in each of the Cases. The Court hereby directs the parties’ counsel to confer with each other and attempt to submit agreed forms of orders to the Court consistent with this Memorandum Opinion and allowing the IRS’ claims in agreed amounts within thirty days of the entry of this Memorandum Opinion on the Court’s docket. If no agreement can be reached, each party shall submit its own proposed form of order on or before the forty-fifth day after entry of this Memorandum Opinion on the Court’s docket, along with an explanation of why the other side’s proposed order is improper.
Attachment
Collateral Estoppel Findings
1. Between 1992 and 1996, Sam and Charles Wyly created a number of IOM trusts, each of which owned several subsidiary companies. Michael French, the Wylys’ family attorney, Sharyl Robertson, the Chief Financial Officer (“CFO”) of the Wyly family office, and Michelle Boucher, the CFO of the Irish Trust Company, a Wyly-related entity in the Cayman Islands, served as protectors of the IOM trusts. French, Robertson, and Boucher conveyed the Wylys’ investment recommendations to the trust management companies administering the Wylys’ IOM trusts (the “IOM trustees”). All of the IOM trustees’ securities transactions were based on the Wy-lys’ recommendations and the IOM trustees never declined to follow a Wyly recommendation.
2. The Wylys served as directors of Michaels Stores, Sterling Software, Sterling Commerce, and Scottish . Annuity and Life Holdings, Ltd. (“Scottish Re”). As part of their compensation, the Wylys received stock options and warrants. “Between 1992 and 1999, Sam and Charles Wyly sold or transferred to the [IOM] -trusts and companies stock • options in Michaels Stores, Sterling Software and Sterling Commerce” in exchange for private annuities while simultaneously disclaiming beneficial ownership over the securities in public filings with the SEC. Between 1995 and 2005, the IOM trusts and companies exercised these options and warrants,*646 separately acquired options and stock in all four companies, and sold the shares, without filing disclosures.
3. The jury found that the Wylys were beneficial owners of the Issuer securities transferred to, held, and sold by the IOM trusts because the Wy-lys, directly or indirectly, had or shared voting and/or investment power over these securities. Thus, the jury concluded that the Wylys failed to accurately disclose the extent of their beneficial ownership in the Issuer securities under sections 13(d) and 16(a) of the Securities Exchange Act (the “Exchange Act”). The jury also found that the Wylys caused the Issuers to violate section 14(a) of the Exchange Act, because the Wylys misrepresented the extent of their beneficial ownership to the Issuers in their Director and Officer (“D & 0”) questionnaires, which were incorporated by the Issuers in proxy statements.
4. In addition to these disclosure violations, the Wylys were found liable for securities fraud in violation of section 10(b) of the Exchange Act and section 17(a) of the Securities Act of 1933 (the “Securities Act”), and for aiding and abetting the Issuers’ and the IOM trusts’ securities law violations.
5. In early to mid-1991, Sam Wyly asked Robertson to attend a seminar held by lawyer and trust promoter David Tedder on the use of foreign trusts as a method of asset protection and tax deferral. Shortly thereafter, the Wylys, Robertson, and French attended another Ted-der seminar in New Orleans. Ted-der, French, and the Wylys then had a private meeting at Sam Wyly’s house in Malibu, California. At that meeting, Tedder “talked about establishing trusts that would provide tax deferral, and how the Wylys could transfer assets to those trusts and get tax deferral on the growth of those assets.”
6. Specifically, Tedder recommended transferring the Wylys’ stock options in Sterling Software and Mi-chaels Stores to a foreign trust in exchange for a private annuity “in a tax-free kind of transaction.” Under Tedder’s plan, it was “expressly intended that [the Wylys] ... irrevocably surrender the enjoyment, control, ownership, and all economic benefits attributable to the ownership of the [options] which are sold in exchange for the private annuity.”
7. The Wylys pursued the offshore program primarily for its tax advantages.
8. However, because Tedder suggested transferring stock options in publicly traded companies — Sterling Software and Michaels Stores — any such transaction would implicate the securities laws. French testified that he raised concerns about whether the Wylys would continue to have filing obligations as directors of Sterling Software and Michaels Stores, even after the transfers. Tedder responded that making SEC filings could threaten the Wylys’ tax benefits, because “disclosure of the offshore trusts in SEC filings may lead the IRS to discover and investigate the tax issue, and ... the IRS might use the Wylys’ SEC filings against them if the tax issue was ever litigated.”
9. But Sam Wyly corroborated French’s account by testifying that*647 Tedder told him that SEC filings “could trigger tax problems if you had these things on file and [were] reporting the trust shares on [Schedule] 13Ds.” Further, it would be logical to draw an inference that the Wylys would have been concerned about taking inconsistent positions in their SEC and IRS filings when millions of dollars of tax sav- ■ ings were at stakp.
10. The jury found that the Wylys always had beneficial ownership over the options, warrants, and securities held by the IOM trusts.
11. Thus, the Wylys were obligated to disclose, on the filings required by sections 13 and 16, any time they or the trusts transacted in those securities. Because beneficial ownership under the securities laws turns on having voting and/or investment power, truthful SEC filings would have forced the Wylys to admit having some element of control over the securities held by the trusts. To the Wylys, this would mean conceding some element of control over the trustees. But the Wylys believed — rightly or wrongly — that it was critical to conceal their control of the trustees in order to maintain the tax-free status of the trusts, including income from transactions in the Issuer securities,
12. Footnote 91, (Sam Wyly) (“We took steps to avoid control, and those are steps to create the appearance of avoiding control. It’s reality and it’s appearance. You want the appearance to match the reality.”) Accord PX 890 (11/3/00 email from Robertson to Evan Wyly) (“Remember that it is critical from a U.S. tax standpoint that there is no appearance that the Wyly’s [sic] are in control of the trusts or the protectors.”).
13. Because the Wylys made public filings showing the transfer of options to foreign trusts, and at other times publicized their relationship to the foreign trusts, the Wylys also took, affirmative steps to minimize the trusts’ SEC filings to conceal the ultimate exercise and sale of those options. For example, the Wyly family office tracked the percentage of ownership each trust management company had in a particular Issuer to avoid triggering mandatory SEC reporting. Thus, as Sam Wyly testified, not making SEC filings was logically “something that consistently went on” throughout the duration of the offshore system.
14. Even when it would have been otherwise helpful to assert beneficial ownership over the stock held by the foreign trusts, such as during Sam Wyly’s proxy battle for control of Computer Associates (the acquirer of Sterling Software) in February 2002, the Wylys chose not to do it in fear of inconsistent tax positions. From these facts, it is logical to draw the inference that making misleading statements in SEC filings, or not making SEC filings at all, was part of the Wylys’ plan to maintain the appearance of separation and independence from the foreign trusts.
15. Footnote 95. See PX 1101 (2/26/02 email from Keeley Hennington, tax director and, starting in 2000, CFO of the Wyly family office, to Boucher, attaching Hennington’s note to Sam Wyly) (“The trusts are record*648 owners of the shares on Computer] Associates]’ books. If it is represented [that] there are $2.9 shares [sic], I think it is likely CA may say we show the Wyly’s [sic] only own 1.5M options and again the difference would need to be explained ... Our friendly IRS agent is still looming around and although he has verbally agreed not to look further at any foreign entities or trusts, I would not want to give him any fresh ammunition.”).
16. The Wylys ultimately hired Tedder to help establish thé first group of offshore trusts and subsidiary companies in 1992 (together with the Plaquemines Trust, the “Bulldog Trusts”). These trusts were settled by Sam or Charles Wyly and had beneficiaries including the Wy-lys’ wives and children and several charitable organizations. The trust deeds permitted the protectors to “add[ ] or substitute]” a charitable organization “by notice in writing to the trustees.” These trusts were explicitly set up as “non-grantor trust[s] rather than [ ] grantor trust[s] under Section 671-678 of the Code.” Under the terms of the trusts, no United States beneficiary could receive a distribution from the trust until two years after the settlor’s death.
17. Footnote 97. (Robertson). The 1992 Trusts relevant to the remedies phase are: 1) the Bulldog Non-Grantor Trust; 2) Lake Providence International Trust; 3) the Delhi International Trust; 4) the Pitkin Non-Grantor Trust; and 5) the Castle Creek International Trust. In 1995, the Bulldog Trust settled the Plaquemines Trust, which had a class of beneficiaries including Sam Wyly’s children. These trusts are referred to as the “Bulldog Trusts” for purposes of this Opinion and Order. The terminology was coined by defendants’ expert, Professor Robert Danforth, and has been adopted by the parties in their briefing and argument.
18. In 1993, French approached the law firm of Morgan, Lewis & Brockius (“Morgan Lewis”) to discuss whether the Bulldog Trust was a “grantor or non-grantor trust.” Morgan Lewis prepared a memorandum concluding 1) that there was a “significant risk that the [Bulldog] Trust will be characterized as a grantor trust under § 679 [because] income is being currently accumulated for the benefit of U.S. beneficiaries,” and 2) that “[i]t is also likely that the Trustee’s power to add or substitute other foreign charities (within the class [of beneficiaries]) causes the Trust to be characterized as a grantor trust under § 674. Charles Lubar, the partner at Mor- ■ gan Lewis retained to work on this matter, gave the memorandum to French and spoke with him about its conclusions.
19. The following year, French asked Lubar to advise the Wylys about whether a trust settled by “a foreign person who had done business with Sam Wyly” would be treated ■ as a grantor trust. Lubar advised that “as long as there wasn’t an indirect transfer of assets by the • U.S. person and the foreign person put . the money up, and there were certain powers in the trust, then it would be a foreign grantor trust,*649 and the distributions then would not be taxable.” For the purposes of rendering his opinion, Lubar assumed that the foreign grantor would be the “sole transferor of property to the trust[ ],” unless the taxpayers transferred funds “on an ‘arm’s length’ basis.”
20. In 1994 and 1995, two foreign citizens established several trusts for the benefit of the Wylys and their families (collectively, the “Bessie Trusts”). The Bessie Trust and the Tyler Trust were purportedly settled by Keith King, an individual associated with Ronald Buchanan, an IOM trustee selected by the Wylys, with initial contributions of $25,000 each. However, no such contribution was ever made. The trusts “were settled with a factual dollar bill ... plus an indebtedness of $24,999 each on the part of Keith King as settlor.” That indebtedness was immediately forgiven.
21. Footnote 107. The 1994/1995 trusts relevant to this Opinion and Order are: 1) the Bessie Trust; 2) the La Fourche Trust; 3) the Red Mountain Trust; and 4) the Tyler Trust. These trusts will be referred to as the “Bessie Trusts,” as per Professor Danforth’s grouping.
22. The La Fourche Trust and the Red Mountain Trusts were purportedly settled by Shaun' Cairns, another individual associated with Buchanan, also with initial contributions of $25,000 each. Cairns testified that French prepared letters stating that Cairns was establishing the trusts “to show [his] gratitude for [the Wylys’] loyalty to our mutual ventures and [their] personal support and friendship,” and asked Cairns to sign them. In truth, Cairns had never met nor dealt with the Wylys before establishing the trusts, and had provided only $100 towards the trusts. Shortly after these trusts were settled, Cairns’s trust management company was hired to serve as trustee for some of the Wylys’ IOM trusts.
23. These' transactions were shams intended to circumvent the grantor trust rules. French and Buchanan, acting as the Wylys’ agents, recruited King and Cairns to create a falsified record of a gratuitous foreign grantor trust. The trust documents are admittedly false — King and Cairns never contributed $25,000 towards the initial settlement.
24. There were no gratuitous transfers here. First, I am doubtful that King provided even the factual $1 towards the trusts. In a November 26, 1995 fax to French, Bu- ■ chanan writes that “Keith never produced the money.” Buchanan explains that the King-related trusts “were settled with a factual dollar bill” only so that “there [was] no question of the[ ] [trusts] being voidable by reason of the absence of assets” pending the Wy-lys’ transfer of options. Even if King had contributed the $1, the premise that an unreimbursed dollar bill is sufficient to establish a tax-free foreign grantor trust cannot be taken seriously. Second, Cairns’s transfer of $100 cannot be considered gratuitous because shortly after settling these trusts, he received lucrative work from the Wylys as trustee. Finally, in light of the falsified trust deeds and supporting documentation sur*650 rounding these trusts, it would be unjust to consider anyone but the Wylys to be the true grantors of these trusts.
25. The trusts were administered by professional asset management companies located on the Isle of Man. The trustees were selected by the Wylys or the protectors. The protectors, all of whom were Wyly agents, had the authority to remove and replace trustees. As mentioned earlier, the protectors also transmitted the Wylys’ investment recommendations to the trustees. Defendants have presented no evidence of an investment made by the IOM trusts that did not originate with the Wylys’ recommendations. Nor have defendants presented evidence of an IOM trustee rejecting a Wyly recommendation.
26. The SEC, on the other hand, has identified several transactions where the Wylys bypassed the trustees altogether. In October 2001, Keeley Hennington, who replaced Robertson as the head of the Wyly family office in June 2000, called Lehman Brothers and directed it to sell 100,000 shares of Mi-chaels Stores held by Quayle Limited, an IOM company, at Charles Wyly’s request. Neither Wyly nor Hennington contacted the trustees before placing the sell order. On another occasion in June 2002, Sam Wyly contacted a broker directly and instructed him to “hold on” to 100,000 shares of TYCO stock, overriding a previous order from the IOM trustee, based on an earlier Wyly recommendation, to sell all TYCO shares.
27. The SEC also presented evidence of transactions that no independent trustee would reasonably initiate.
28. For example, on September 26, 1998, Boucher contacted an IOM trust to recommend a ten million dollar investment in the Edinburgh Fund. On September 28, Boucher told the trustee for the first time that the Edinburgh Fund was a fund run by Sam Wyly’s son-in-law and that it did not have a prospectus or subscription documents. Despite knowing nothing about the investment beyond its connection to the Wyly family, the trustee agreed to “forward the necessary instructions to Lehman Brothers.” One day later, Boucher followed up with the trustee “to ask for an update on progress with regard to making funds available for the proposed investment • in the Edinburgh Fund.... [Boucher] mentioned that the Fund had already commenced trading and that the funds would therefore be required urgently.”
29. Some of the Wylys’ recommendations had nothing to do with securities at all. Among the many ■ personal purchases, loans, and investments the Wylys directed the IOM trustees to make, were businesses for Wyly children and family members, real estate, artwork, jewelry, collectibles, and furniture.
30. “In April 1992, Sam and Charles Wyly transferred 960,000 Michaels Stores options and 1,983,588 Sterling Software options to ten Nevada companies indirectly owned by two Isle of Man trusts in exchange for deferred private annuity agreements.” In 1995 and 1996, the Wy-lys transferred 1,350,000 Michaels*651 Stores options, 2,650,000 Sterling Software options, and 4,600,000 Sterling Commerce options to the IOM trusts, also in exchange for annuities.
31. In June 1997, French approached Morgan Lewis to discuss the tax consequences of the private annuity transaction. Lubar remembers that he was “really concerned about the transaction” and “worried that the transfer of the options to a company that didn’t have any other assets in exchange for a private annuity raised a question about whether that was an arms-length transfer.” However, Lubar acknowledged that “other tax lawyers would look at a transfer of a private annuity in different ways.”
32. After studying the issue, Lubar advised French that the transfers created potential problems under sections 674 and 679, amongst other provisions.
33. Ordinarily, a company granting stock options as compensation issues a Form 1099 or W2 reporting income to the director or officer and takes a corresponding deduction for the compensation expense when the option is exercised. When the Wylys transferred- their stock options to the IOM trusts in exchange for private annuities, the Issuers of the options — that is, Sterling Software and Michaels Stores — had to decide whether that transfer was a taxable event that .required issuing a Form 1099 or W2 to report income to the Wylys. . To address these concerns, Tedder sent an opinion letter to both companies explaining that the Wylys should not have to recognize income because the annuity did not require payment until a date certain in the future.)
34. Jeannette Meier, general counsel of Sterling Software, asked French’s law firm, Jackson Walker, to give a “back up” tax opinion to support Tedder’s letter. French provided a draft opinion, but never finalized the letter. Nevertheless, based on French and Tedder’s representations, Sterling Software decided not to issue a Form 1099 to the Wylys and declined to take a corresponding deduction for compensation expense. But Meier testified that the company was “concerned about ... whether, not having gotten a backup opinion from Jackson Walker, [it] was on good ground not to have to put [the compensation expense] in the [Section] 10-Q [financial statements.]” The value of the options was “a big number” and “would have affected the accuracy of the public filings” if Sterling Software had decided to report it ■ as compensation.
35. Michaels Stores treated the transfer of options identically. In addition, French instructed Mark Beasley, general counsel for Michaels Stores, not to issue Form 1099s for -any of the foreign trust entities upon those companies’ exercise of stock options.
36. In March 2000, SBC Communications Inc. (“SBC”) acquired Sterling Commerce, which had been spun off from Sterling Software in 1995. “As part of [the] acquisition ... all outstanding options to purchase shares of Sterling [Commerce] were canceled. All option holders received cash .., based on the excess of the stock purchase*652 price over the option price.” On January 11, 2001, SBC notified the Wylys that it was planning “to issue a Form 1099 to [the respective Wylys]/[their] trusts showing taxable income” in the total amount of $73,912,500. The Wylys, through Boucher and Robertson, reached out to Rodney Owens, a partner at the Meadows Owens law firm in Dallas, to write a memo to SBC explaining why a 1099 should not be issued. On January 26, 2001, Owens wrote in a letter to SBC that “it is-not appropriate for SBC to file a 1099 or any other reporting papers regarding this transaction because [the IOM entity] is a foreign corporation, and the income from the purchase of the stock is not subject to U.S. taxation.” After receiving the letter, SBC sought additional information about the private annuity transaction, including whether the transfer of options had been recognized as a taxable event at the time of the original transaction, and if not, what the schedule of annuity payments was. Although French’s relationship with the Wylys had broken down by this point, he agreed to write a memorandum supporting the tax treatment of the annuities.
37.All in all, between 1992 and 2004,-the Issuers never reported income related to the exercise of options or warrants transferred to the foreign trusts. Their decision not to report was a result of the Wylys’ deceptive behavior and affirmative misrepresentations. Because the Wy-lys disclaimed beneficial ownership of the options upon transfer, convinced the Issuers that the private annuity transactions were not taxable events, and did not disclose their beneficial ownership of the securities held by the IOM trusts in their Director and Officer questionnaires, the Issuers did not attribute taxable income to the Wy-lys.
38. The annuity payments for the original option transfers had been due to commence in the late 1990s, but that period was extended to 2004. In early 2003, Boucher and Hen-nington approached Lubar to discuss potential issues arising from the upcoming annuity payments. Lubar told Hennington and Boucher that, as he explained to French years before, he believed the trusts were grantor trusts under either sections 674 or 679 and should have been taxable to the Wylys all along. Further, Lubar believed the IRS would challenge the private annuity transactions. Lubar and other Morgan Lewis attorneys suggested approaching the IRS “on a no-name basis” to see “where the negotiations with the IRS might lead” in the event the Wylys wanted to pursue a voluntary disclosure.
39. Boucher and Hennington summarized Lubar’s advice in a July 2, 2003 memorandum to Sam Wyly, Charles Wyly, Evan Wyly, and Donald Miller. The memorandum addressed several concerns about the “logistical problems of paying the annuities.” Hennington and Boucher were concerned that “[i]t is almost certain given the large amount of these payments that the reporting will result in an IRS audit. [Further], [t]here is also a high likelihood that as a result of this audit the entire structure of*653 the foreign system will be audited by the IRS.”
40. Additionally, Hennington and Boucher reported that [t]he annuity payments will bankrupt several of the IOM companies, which could bring the validity of the annuity transaction into question. [And] [a]fter a few years ■ of payments, [other] companies will be left with non-liquid assets, which will result in payments being made in kind ... [which] may also call into question the validity of the transaction and the ‘arms length’ nature of the transaction.
41. On August 13, 2003, several attorneys representing the Wyly family met with Internal Revenue Service (“IRS”) officials. Lubar gave the IRS some details about the trusts, and admitted that there was a “serious risk [that] they were grantor trusts from the beginning.” Lubar also explained the private annuity transactions, and told the IRS, after questioning, that the options were for stock in publicly traded corporations, that no income was reported upon exercise, and that the corporations claimed no deductions.
42. According to attorney notes memorializing the meeting, an IRS officer asked if the taxpayers were “significant enough shareholders that their holdings would be listed on SEC filings” and asked if the “SEC filings show[ed] beneficial interest in shares.” Lubar said that he believed they were significant enough shareholders for “at least [the] first two [companies]” but did not know if the filings showed beneficial ownership. Hennington and Boucher reported to the Wylys that the IRS was primarily interested in the structure of the annuity, but added that one of the IRS representatives “seemed very interested in any SEC reporting of the initial transactions [even though] [t]his seems out of their area of expertise or control.”
43. The Wylys did not proceed with Morgan Lewis on a voluntary disclosure path. But by February 2, 2004, Charles Wyly received a notice of audit. Shortly thereafter, Sam Wyly asked Hennington, Boucher, and Charles Pulman, another attorney at Meadows Owens, “to explore what happens [for purposes of .taxation] if he is not a U.S. citizen.” The firm concluded that an expatriate U.S. citizen who has a net worth of more than $622,000 “will be treated as having a principal purpose of tax avoidance” and will continue to be taxed pursuant to several special provisions.
44. From May to August 2004, the IRS sent a number of information document requests (“IDRs”) to both Sam and Charles Wyly. In at least one of the IDRs, the IRS requested additional information about a transfer of Michaels Stores options to an independent trust, such as “the identity of all original and current beneficiaries, including their nationality, place of residence, and current mailing address” as well as the identity of “the grantor(s) of the trust(s).” At an October 21, 2004 meeting between attorneys representing the Wyly family and the IRS, an IRS agent said that the IDRs regarding the options transfers were based on information “pulled from SEC filings.” At that*654 meeting, the IRS agents also asked questions about the trusts, including about why Keith King set up the Tyler Trust.
45. The SEC has not shown that the Wylys’ or Issuers’ SEC filings • launched the IRS audit of the Wy-lys and the offshore system, or even that accurate filings would have been likely to trigger an earli- ■ er examination. However, it is evident from the IDRs and from the October 2004 meeting, that once the IRS investigation was under way, agents and investigators were consulting SEC filings as part of their fact finding process and identified numerous issues and misstatements.
46. The IOM trusts sold 1.8 million shares of unregistered stock between June and December 1997, at prices ranging from approximately $21 per share in the summer to approximately $35 per share in the fall. The trusts sold 200,000 of these shares less than one year after the December 1996 private placement, in violation of the terms of the purchase agreement. In 1998, the IOM trusts sold a small number of shares at approximately $32 per share. In 2000 arid 2001, the IOM trusts sold approximately 1.2 million shares at prices ranging from approximately $40 per share in September 2000 to approximately $55 per share in November 2001.
47. Defendants must concede that if I .conclude that the Wylys were the real grantors of the Bessie Trusts, then the profits earned on the sale of Issuer securities by those trusts are taxable to the Wylys, not the purported foreign grantors. Because I conclude that the purported foreign grantors made no gratuitous contributions, “the trusts at issue [are] clearly grantor trusts taxable to the domestic grantors.”
48. Section 674(a) provides that: “[t]he grantor shall be treated as the owner of any portion of a trust in respect of which the beneficial enjoyment of the corpus or the income therefrom is subject to a power of disposition, exercisable by the grantor or a nonadverse party, or both, without the approval or cori-sent of any adverse party.” Quoting a prominent tax treatise, defendants concede that the “power of disposition” includes “powers to ‘effect such major changes in the enjoyment of a trust’s income and corpus as the addition and elimination of beneficiaries’ as well as ‘minor and customary power[s]’ over income and corpus distribution.” Because a non-beneficiary trustee is considered a non-adverse party under the. statute, “[s]ection 674(a) captures virtually every trust, including the [IOM] trusts.” Thus, defendants concede that “[ultimate liability under [s]ection 674[ ] ... turns on whether any of the statutory exceptions apply.”
49. According to defendants, the Bulldog Trusts are not grantor trusts because they fall under the section 674(c) exemption. Under that exemption, section 674(a) does not apply to “certain powers that are exercisable by independent trustees.” According to the corresponding IRS regulation, which summarizes the statute, [t]he powers to which section 674(c) apply are powers (a) to distribute, apportion, or accumulate income to or for a beneficiary*655 or beneficiaries, or to, for, or within • a class of beneficiaries, or (b) to pay out corpus to or for a beneficiary or beneficiaries or to or for a class of beneficiaries (whether or. not income beneficiaries). In order for such a power to fall within the exception of section 674(c) it must be exercisable solely (without the approval or consent of any other person) by a trustee or trustees none of whom is the grantor and no more than half of whom are related or subordinate parties who are subservient to the wishes of the grant- or.
50. To determine whether the Bulldog Trusts are covered by this exception, it is necessary to answer three questions: 1) Did the IOM trustees have the power to “distribute, apportion, or accumulate income” or “pay out coipus” to or for a beneficiary or beneficiaries?; 2) Were the IOM trustees a) the grantor, or b) a “related or subordinate” party as defined by the statute?; and 3) Were the trustees able to “exer-cis[e] [those powers] solely (without the approval or consent of any other person)”?
51. The first two questions are straightforward. First, the IOM trustees certainly had the power, as set out in the trust deeds, to “distribute, apportion, or accumulate income” or “pay out corpus” to or for a beneficiary. Second, the IOM trustees were neither the grantor, nor one of the individuals on the exclusive list of “related or subordinate” parties defined by the stab ute. The only remaining question is whether the IOM trustees were able to exercise those powers “solely” or “without the approval or consent of any other person.”
52. The Wylys, through the trust protectors who were all loyal Wyly agents, retained the ability to terminate and replace trustees. The Wylys expected that the trustees would execute their every order, and that is exactly what the trustees did.
53. The evidence amply shows that the IOM trustees followed every Wyly recommendation, whether it pertained to transactions in the Issuer securities, making unsecured loans to Wyly enterprises, or purchases of real estate, artwork, collectibles, and other personal items for the Wylys and their children. The trustees made no meaningful decisions about the trust income or corpus other than at the behest of the Wylys. On certain occasions, such as the establishment of the Bessie Trusts, the IOM trustees actively participated in fraudulent activity along with the Wylys. The Wylys freely directed the distribution of trust assets for personal purchases and personal use. Because the Wylys and their family members were beneficiaries, the IOM trustees were thus “distributing” income for a beneficiary at the direction of the grantors — the Wylys.
54. Footnote 218. Because I conclude that both the Bulldog and Bessie Trusts were grantor trusts under Section 674, I need not reach the issue of whether they were also grantor trusts under Section 679.
55. The Wylys engaged in a thirteen year fraud, creating seventeen trusts and forty subsidiary companies, employing numerous IOM trustees, a veritable “army of law*656 yers,” hiring an offshore accountant to hold records outside the United States, and delegating several domestic employees to handle the administration of the trusts.
56. Reasonable and savvy businessmen do not engage in such activity unless it is profitable. Of course it was profitable — by transferring property, including valuable options and warrants, to the trusts, exercising the options and trading in secret, and using the proceed to reinvest in other ventures, the Wylys were able to accumulate tremendous tax-free wealth.
57. The jury found that the Wylys were beneficial owners of all of the Issuer securities — from the time the options were transferred to the trusts to the time, the trusts exercised the options or otherwise acquired stock to the time they were sold. The jury also found that the Wylys’ pervasive failure to disclose beneficial ownership constituted securities fraud. There is no evidence in the record that the purpose of this fraud was to manipulate or distort the market.
58. There is ample evidence, however, that the driving purpose of the securities fraud was to conceal the Wylys’ relationship to the IOM trusts and preserve the preferential tax treatment, on secret offshore profits for as long as possible.
59. First, defendants’ motivation to preserve tax benefits was important to their decision to misrepresent their beneficial ownership. Admitting beneficial ownership would have forced defendants to take conflicting positions with two separate government agencies. Even if admission of “beneficial ownership” on a schedule 13D would not immediately reveal a fact that would establish control of an offshore trust, it would at .least be facially inconsistent with a tax reporting position that did not include the profits from trades made by that offshore trust. It would have been reasonable, and in fact, prudent, for the Wylys to be concerned about taking conflicting positions in public SEC filings and on their tax returns because that SEC filing could constitute an admission for purposes of future tax litigation.
60. Given the Wylys’ high profile background, tremendous wealth, and history of litigation with the IRS, the possibility of an IRS audit was not remote. In fact, it was highly likely. Thus, even if the Wylys had no reason to believe that SEC filings could trigger an audit, they certainly had reason to believe and fear that the IRS would consult all public filings in the event of an audit.
61. Second, the securities fraud was intimately connected to protecting the tax benefits in other ways. The Wylys took numerous steps to prevent the. Issuers from issuing Forms 1099 to report income to either the Wylys in an individual capacity or to the offshore entities. The Issuers did- not report income to the Wylys after the 1992 private annuity transaction because of the Wylys’ misrepresentations about disclaiming beneficial ownership over the options, and French and Tedders’ misrepresentations about the economic substance of that transaction.- In 2001, nearly ten years later, the Wylys continued*657 the fraud by convincing SBC not to issue 1099s based on the same misrepresentations. None of the four Issuers reported income to the Wy-lys in connection with the options granted as compensation and transferred to the trusts, even though the Wylys certainly enjoyed the benefit of those options once they were exercised and the stock was sold.
62.The Wylys engaged in securities fraud to conceal their relationship to and control of the IOM trusts in order to maintain the secrecy of the offshore system and preserve their tax benefits. The unlawful gains causally related to the securities violations found by the jury, is an amount equivalent to the taxes avoided on the profits the Wylys realized on the sale of Issuer securities.
63. The Wylys’ securities violations helped them establish the offshore system, conceal their trading profits, and use those trading profits to invest in other ventures and amass tremendous untaxed wealth.
64. Sam Wyly engaged in a large securities fraud spanning thirteen years, involving multiple trusts and entities and hundreds, if not thousands, of misstatements, all while being subject to a previous injunction entered in 1979.
. See Debtor Sam Wyly’s Objection to Proof of Claim No. 18 Filed by the IRS [ECF No. 938] and Debtor Caroline D. Wyly's Amended Objection to Claim Number 11 of the Department of Treasury — Internal Revenue Service [Case No. 14-35074, ECF No. 75].
. To the extent that a finding of fact is more properly construed as a conclusion of law, or vice versa, it should be so construed.
.11 U.S.C. § 505 expressly provides that a bankruptcy court may determine a debtor’s tax liability:
(a)(1) Except as provided in paragraph (2) of this subsection, the court may determine the amount or legality of any tax, any fine or penalty relating to a tax, or any addition to tax, whether or not previously assessed, whether or not paid, and whether or not contested before and adjudicated by a judicial or administrative tribunal of competent jurisdiction.
(2) The court may not so determine—
(A) the amount or legality of a tax, fine, penalty, or addition to tax if such amount or legality was contested before and adjudicated by a judicial or administrative tribunal of competent jurisdiction before the commencement of the case under this title[J
. See I.R.S. v. Luongo (In re Luongo),
. The Court wishes to express its appreciation to the parties for the enormous efforts that went into simplifying this trial whenever possible. The Joint Stipulations and the Computation Stipulations saved weeks of trial testimony.
. Dee is Charles’ widow. Dee and Charles were married for 56 years and they filed joint tax returns throughout their marriage.
. SEC v. Wyly,
. See Memorandum Opinion Exhibit A. The Court will cite to these findings by the' number assigned to each on Exhibit A (e.g., Collateral Estoppel No. 1).
. This Court heard substantial evidence that overlaps with that the jury and the SDNY Court heard in the SEC Action. While various witnesses who testified there were not called here, the parties agreed to rely on their testimony in the SEC Action here. While this Court did not retry the legal determination of whether the Bulldog Trusts and the Bessie Trusts (as defined by the SDNY Court) were grantor trusts to Sam and Charles, having decided to apply collateral estoppel to that determination of the SDNY Court at the IRS’ request, many of the factual findings made there (and to which this Court has applied collateral estoppel) were proven here also. Where the Court quotes from findings of fact made in the SEC Action in this Memorandum Opinion to which it has applied collateral estoppel, the Court will also note if that finding was independently proven here too. Unless the Court specifically notes otherwise, the finding here was proven by clear and convincing evidence.
, At certain points in this Memorandum Opinion, the Court refers to understatements of income instead of underpayments of income taxes. The parties agree that it is the Debtors’ respective understatements of income that resulted in their respective underpayments of income taxes here.
. This agreement is contingent upon (i) the SDNY Court's determination of foreign grant- or trust status being affirmed on appeal, which appeal is currently pending before the Second Circuit Court of Appeals, and/or (ii) this Court’s collateral estoppel decision being affirmed on appeal, assuming such an appeal is taken.
. 26 U.S.C. § 7701(a)(31). Prior to August 20, 1996, a "foreign” trust was defined as a trust "the income of which, from sources without the United States which is not effectively connected with the conduct of a trade or business within the United States, is not includible in gross income under subtitle A.” 26 U.S.C. § 7701(a)(31) (1996).
. 26 U.S.C. § 7701(a)(30)(E).
. Robert T. Danforth, et al. TAX TREATMENT OF GRANTOR TRUSTS ¶7.01,
. 26 U.S.C. § 671-79.
. Tr. Trans. 331:18-24 (Cole).
. Appendix to Rubenstein Motion [ECF No. 926] at App. 0004.
. Id.
. Askanase v. Fatjo,
. See Fed. R. Evid. 702; Daubert v. Merrell Dow Pharm., Inc.,
. See Rubenstein Motion at 20-22.
. See Askanase,
. See Askanase,
. Tr. Trans. 450:20-452:4 (Rubenstein). Citations in this Memorandum Opinion to "Tr, Trans.” refer to the transcript of the January 2016 trial on the Motions and Claim Objections, while citations to "SEC Tr. Trans.” refer to the trial transcript in the SEC Action. The pin cites are pagedine— pagedine.
. See, e.g., id. at 468:22-469:13 (Rubenstein) (discussing uncertainty among practitioners during the relevant time period as to how to treat a trust with only contingent United States beneficiaries under 26 U.S.C. § 679).
. Appendix to Rubenstein Motion [ECF No. 926] at App. 0004.
. Owen v. Kerr-McGee Corp.,
. U.S. v. West,
.
.
. Burton,
. As explained infra at pp. 371-74, 413-16, French (who served as the Wylys primary counsel and trusted agent for about twenty years, IRS Ex, 1199 ¶ 4 (p. 6)) learned in 1993 that an experienced international tax lawyer, Charles Lubar, who French hired on the Wy-lys’ behalf, believed that the 1992 IOM trusts were properly characterized as foreign grant- or trusts as to Sam and Charles. The Court imputes this knowledge to Sam and Charles under agency principles.
. See pp. 371-74, infra.
. See Tr. Trans. 513:23-514:22 (Ruben-stein).
. There is no evidence suggesting that Dee was involved in any decisions regarding the structure of the offshore system at issue here. Nor is there any evidence suggesting that Dee knew of any uncertainty in the law during the relevant time period. Thus, Rubenstein’s testimony has virtually no relevance as to Dee.
. Askanase,
. As explained by Rubenstein, a trust protector is an intermediary between the settlor of a trust and its beneficiaries, on the one hand, and the trustee, on the other hand. Trust protectors are usually individuals. Tr. Trans. 355:9-16 (Rubenstein).
. As explained by Rubenstein, an accommodation grantor describes a situation where a third party creates and forms a trust as an accommodation to the person who is going to grow the wealth in that trust. Id. at 479:2-8 (Rubenstein).
.
.
. Gibbs v. Gibbs,
. See Seatrax, Inc. v. Sonbeck Intern., Inc.,
. See U.S. v. Tucker,
. Daubert,
.
.
. See Skidmore v. Precision Printing and Pkg., Inc.,
. Kumho Tire Co., Ltd.,
. Tucker,
. See Fed. R. Evid. 702 advisory committee’s note to 2000 amendment (“it might also be important in some cases for an expert to educate the factfinder about general principles, without ever attempting to apply these principles to the specific facts of the case ... The amendment does not alter the venerable practice of using expert testimony to educate the factfinder on general principles.”); see also Daubert,
. See Tr. Trans. 511:24 (Rubenstein) ("I’m not opining on what the Wylys did,”),
. See Tr. Trans. 513:23-514:22 (Ruben-stein).
. Cf. Daubert,
. See Wyly Ex, QN (Rubenstein's CV detailing his extensive experience); Hr’g Trans. January 5, 2016 46:1-51:20 (Rubenstein’s testimony at the Daubert hearing regarding his qualifications), 51:21-59:25, 68:8-11 (Ruben-stein’s testimony at the Daubert hearing discussing how he formed his opinions); Tr. Trans. 333:9-335:16 (additional trial testimony by Rubenstein discussing his qualifications); 418:16-22 (additional trial testimony by Rubenstein discussing how he formed his opinions).
.* See Tr. Trans. 499:9-15 (Rubenstein).
.
. See id.
. Gulf State Util. Co. v. Ecodyne Corp.,
. See Rubenstein Motion at 20-22.
. Roman v. Western Mfg., Inc.,
. Dixon v. Int’l Harvester Co.,
. Hidden Oaks Ltd. v. City of Austin,
. See Wyly Ex. QN (Rubenstein’s CV).
. See Hr’g Trans. January 5, 2016 55:1-15 (Rubenstein) (‘‘Well, the private annuity rules don’t make any difference on the private annuity side whether you do it with an individual with a domestic trust or foreign trust. There are different estate tax concerns when you do them with trusts, specifically foreign trusts, that make it riskier. So during that time period, I did that for people in their individual capacities as opposed to adding the estate tax complications.”).
. Tr. Trans. 390:18-25(Sam).
. Id. at 390:19-394:10(Sam).
. Id. at 398:9-400:6(Sam).
. Id. at 401:22-402:22(Sam).
. Id. at 402:23-408:5(Sam).
.Id. at 408:15-409:8(Sam),
. Id. at 409:9-411:19(Sam).
. Joint Stipulations ¶ 2.
. Id. '
. Id. ¶ 4.
. Id.
. id. 115.
. Id.
. IdA 3.
. Id.
. Id. ¶ 8.
. Id. ¶ 10.
. IdA 9.
. IdA 6.
. IdA 16.
. Id. ¶ 16; Tr. Trans. 423:6-24(Sam).
. Joint Stipulations ¶ 17.
. Id.
. IdA 11.
. Id.
. SEC Tr. Trans. 1697:9-12 (French).
. Id. at 1697:11-12 (French).
. Id. at 1698:6 (French).
. Id. at 1697:9-10 (French).
. Tr. Trans. 698:17-699:14(Sam).
. SEC .Tr. Trans. 1710:19-25, 1711:9-15 (French); IRS Ex. 1199 ¶ 25 (p. 10) (Annex A, Admissions of Defendant Michael C. French),
. IRS Ex. 1199 ¶ 26 (p. 10) (Annex A, Admissions of Defendant Michael C. French).
. Id.
. Joint Stipulations ¶ 12.
. Tr. Trans. 149:20-15:14(Dee).
. See Appendix to Debtor Caroline D. Wyly's Motion for Partial Summary Judgement [ECF No. 880] at app. 46 (deposition excerpt).
. Tr. Trans. 150:24-15 l:7(Dee) (one of the children did not survive to adulthood), 168:5-15(Dee).
. Id. at 168:5-15(Dee).
. Id. at 151:8-152:2(Dee).
. Id. at 151:8-152:2(Dee), 168:5-15(Dee).
. Collateral Estoppel No. 5; SEC Tr. Trans. 156:25-157:7 (Robertson); Robertson Dep. Tr. 76:19-77:2; IRS Ex. 85 (June 12, 1991 memorandum from Robertson to Sam, Charles, Evan, French, and Ethel Ketter, in-house CPA for the Wyly family office, discuss
. IRS Ex. 85.
. Id. at SEC00150261 (under section titled "Goals”).
. At trial, Sam admitted that the term “creditor” includes the IRS, which is the largest creditor in the Cases. Tr. Trans. 1047:24-1048:8, 1364:2-4 ("Q. By 'asset protect,’ you meant the risk that creditors could get to your assets, is that correct? A. Yes. Q. And one of those creditors would include the Internal Revenue Service. Is that correct? A. Yes.”).
. IRS Ex. 85 atSEC00150261.
. Id. at SEC100150263 (under heading "Items to be Prepared to Do”),
. Id. at SEC100150281 (under heading "Problems").
. IRS Ex. 525.
. Id. at SWYLY004776.
. Collateral Estoppel No. 5; Tr. Trans. 696:23-627:16 (Sam, however, testified that he did not attend the New Orleans conference); SEC Tr. Trans. 168:2-12 (Robertson testifying that she attended the New Orleans seminar along with Sam, Charles, and French), 1716:14-1717:3 (French testifying he attended the New Orleans seminar with Sam and Charles).
. French Depo Tr. 1717:1-20.
. Collateral Estoppel No. 5; Tr. Trans. 1050:19-1059:ll(Sam); IRS Ex. 525; SEC Tr. Trans. 1718:4-8 (French).
. Tr. Trans. 1050:23-1059-30(Sam); SEC Tr. Trans. 1719:7-17 (French); IRS Ex. 525.
. Collateral Estoppel No. 6; Tr. Trans. 1050:19-105 l:16(Sam), 1052:9-1059:ll(Sam); SEC Tr. Trans. 1719:3-17 (French); IRS Ex. 525 (written information Sam received from Tedder titled "An Overview of Asset Protection Estate and Income Tax Reduction Using Domestic and International Structures”).
. Joint Stipulations 110-111 (stipulations as to formation and ownership structure); SEC Tr, Trans. 1008:6-1011:20 (Boucher testifying that documents were moved and kept offshore to, among other reasons, make them more difficult for third parties to obtain); IRS Ex. 1199 ¶61 (p. 15) (Annex A, Admissions of Defendant Michael C. French) ("One purpose of Boucher’s employment was to maintain records for the Isle of Man Trusts and the Offshore Companies in the Cayman Islands so that the records would not be maintained in the United States.”); Tr. Trans. 1370:1-6 (Sam testifying that one of the purposes for hiring Boucher was so that records would not be maintained in the United States); IRS Ex. 95 at SWYLY013049, § l.C (Memorandum dated May 12, 2000 from Robertson to Sam, Evan, and others expressing a concern regarding future regulations that may require submission of audited financial statements and access to offshore trust documents, and stating the "solution” of hiring a " 'lawyer’ custodian to hold the trust deeds, which disclose beneficial ownership. The lawyer would be instructed by the protectors and the trustee not to release the trust deeds to anyone without joint consent. This would slow the process of delivery of the trust deeds down, giving the ability to flee the jurisdiction if it was deemed necessary.”).
.Joint Stipulations ¶ 68; Tr. Trans. 556:24-557:12 (Evan).
. Tr. Trans. 1744:1 l-16(Sam).
. Id. at 556:24-557:12 (Evan).
. Id. at 556:24-557:12, 559:1-14 (Evan): Joint Stipulations ¶ 113..
. Joint Stipulations ¶ 113.
. SEC Tr. Trans. 987:4-988:4 (Boucher).
. Id. 995:25-996:17 (Boucher).
. Tr. Trans. 787:19-21, 912:18-913:3 (Evan).
. IRS Ex, 409.
. Id. at 81822-823 (emphasis added).
. French’s concerns about the proper tax treatment of the 1992 IOM trusts and his decision to get a second opinion from Lubar’s firm are discussed in detail infra at pp, 413-16.
. Tr, Trans. 1925:3-1968:9 (Hennington testifying regarding the series of events that occurred after Boucher's chance meeting with Lubar at a conference in the Cayman Islands).
. IRS Ex. 96 (memorandum dated June 30, 2003 prepared by Hennington to inform the Wyly family of the issues that Lubar had raised); Tr. Trans. 1945:17-1949:21 (Hen-nington prepared the memo for the purpose of "relaying all of the issues that Lubar had raised” and to provide the "worst-case scenario” to the family), 1949:22-1954:19 (Hen-nington recounts a meeting with the Wyly family to discuss the worst-case scenario and Lubar's recommendation that he meet with the IRS on their behalf on an anonymous basis),
. Tr. Trans. 592:19-596:8 (Evan), 844:5-8, 960:9-17 (Evan) ("This was a sutprise_ In fact, this was a surprise because it was the opposite of what we had been hearing all along.”), 970:10-24 (Evan), 1776:18-24 (Cousins) (“I believe that they were very, very upset because Mr. Lubar indicated there was a problem with the '92 trusts, and they didn’t know that there was going to be a problem and didn't know what to do about it.”), 1944:16-19 (Hennington) (“Q: Did you understand Mr. Lubar to be raising issues that were inconsistent with the advice previously given by Meadows Owens concerning the trusts? A: Absolutely,”), 1349:20-1349:24 (Donnie Miller) (“Q. Was it fair to say that pretty much Charles Wyly, Sam Wyly, Evan Wyly, everyone intimately connected with this offshore structure was discomposed, to say the least, by this memo. A. Yeah. We were surprised,”), 1358:3-1359:9 (Donnie Miller) (Surprised by memo in 2003 because “I thought we were always compliant with regulations”).
.Tr. Trans. 1409:9-1423:16 (Sam's testimony regarding IRS Ex. 96, which contains the mid-2003 memoranda in which Henning-ton and Boucher expressed Lubar’s conclusions regarding issues surrounding the trusts). Sam’s testimony consists mainly of him acknowledging that the IRS’ counsel correctly • read the document into the record. Although Sam claims he does not remember the memorandum, he admits that he likely would have received it due to its importance and the fact it was sent by Hennington and Boucher. Further, when asked whether French had conveyed Lubar's concerns raised in 1993 regarding the status of the 1992 trusts, Sam simply testified "I don’t know.” Id. at 1419:5-11. And, when questioned as to whether this was too important of a topic for French not to have informed Sam, Sam testified: “[i]t’s certainly an important topic, but it’s the sort of thing delegated to attorneys — to Mr. French and other attorneys.” Id, at 1420:17-21. Sam, however, did not testify as to any surprise in 2003 when he heard the news; he simply testified that he could not remember whether he was previously told. Remarkably, on redirect, Sam unequivocally testified that neither Owens, French or any of Sam’s lawyers or CPAs ever told him that was anything seriously wrong with the IOM trusts “as a tax matter.” Id. 2935:12-23(Sam). This is just one example of the many times that Sam’s memory on redirect was superior to that during cross.
. Id. at 976:9-18 (Evan), 1936:6-1944:1 (Hennington), 1956:12-19 (Hennington).
. Id. at 1956:20-1958:23 (Hennington).
. Meadows Owens gave no formal written opinion letters to the Wylys. Rather, Meadows Owens’ advice was provided orally or in less formal writings. As will be discussed in detail in connection with the Court’s analysis of Sam’s reasonable cause and good faith defense, he received advice from numerous lawyers and other professionals about the offshore system and the tax consequences of it to him from 1992 to the present. See pp. 475-513, infra.
. Tr. Trans. 970:25-971:6, 976:2-8 (Evan).
. Id. at 1774:4-5 (Cousins) (Owens passed away in July 2003); 1970:5-1972:13 (Hen-nington).
. IRS Ex. 98 at WYLYSEC01105084 (Notes from October 8, 2003 meeting between various Meadows Owens attorneys and Henning-ton detailing options and recommending the filing of a Form 8275), Joint Ex. 106 (Sam’s 2002 tax return) at SWYLY021498-500 (Attachment to Form 8275).
. Joint Ex. 130 (Dee and Charles’ 2003 tax return) at SWYLY029540-542 (Attachment to Form 8275).
. Tr. Trans. 2073:21-2074:13 (Hennington) (‘‘[The IRS] made clear that [the foreign trusts and annuities] was the focus of their audit when they started in ’04.”).
. Id. at 2114:9-16 (Hennington).
. Id. at 2114:20-2115:21 (Hennington).
. Upon the Debtors’ applications, Lan was retained as special tax counsel here, after notice and a hearing. See employment orders at ECF No. 261 and 367 (Kroney Morse Lan, PC employment orders) and 749 and 750 (Lan Smith Sosolik, PLLC employment orders).
. Tr. Trans. 2076:21-2078:24 (Henning-ton).
. See IRS Ex. 1199 (Consent of Michael C. French).
. SEC v. Wyly,
. In the body of this Memorandum Opinion, the Court will refer to a specific Bankruptcy Rule of Procedure as "Bankruptcy Rule” followed by the applicable rule number.
. Fed. R. Bankr. P. 3001(f); see In re Fidelity Holding Co., Ltd.,
. Fidelity Holding Co., Ltd.,
. Simmons v. Savell (In re Simmons),
. Raleigh v. Illinois Dept. of Revenue,
. See In re 1701 Commerce, LLC,
. Debtors' Brief in Support of Motion for Order Determining the Respective Burdens of Proof [ECF No. 936] ("Debtor’s Burden of Proof Brief ”) ¶ 3.
. Id. ¶11.
. Id. ¶ 14.
. Id. ¶ 18.
.Id. ¶¶ 16-17.
.The Fifth Circuit, agreeing with many other courts that have explored the operation of burden shifting in the tax context, has pointed out that “the operation of this burden-shifting scheme is irrelevant when both parties have met their burdens of production and the preponderance of the evidence supports one party.” Brinkley v. C.I.R.,
The parties here have presented mountains of evidence, and so the Fifth Circuit's observations that allocation of burden of proof is sometimes unimportant may well apply here. Of course, this “it makes no difference” caveat does not apply to the IRS’ burden for its assertion of fraud penalties, as the IRS must prove fraud by clear and convincing evidence, not a preponderance of the evidence. Out of an abundance of caution, however, this Court undertakes the burden of proof analysis.
. See Case No. 14-35043, Claim No. 18 at 3; Case No. 14-35074, Claim No. 11 at 3.
. See Case No. 14-35043, Claim No. 18 at 3; Case No. 14-35074, Claim No. 11 at 3.
. Fed. R. Bankr. P. 3001(c)(2)(D)(i).
. Tr. Trans. 1582:23-1596:1 (Herrick).
. Id. at 2766:21-2769:5 (Pfiffner),
. Fed. R. Bankr. P. 3001 advisory committee's note to 2011 Amendments (emphasis added).
. See, e.g., Tr. Trans. 1633:1-1637:23 (Carey).
. In re Fuller,
.Tr. Trans. 1648:7-12 (Carey).
. In re Today's Destiny, Inc.,
. See Debtors’ Burden of Proof Brief [ECF No. 936] ¶ 20.
. See Carlisle v. Dept. of Justice (In re Carlisle),
. Tr. Trans. 2766:21-2769:5 (Pfiffner).
. In re Davis,
. Debtors' Burden of Proof Brief [ECF No. 936] ¶ 4.
. In re Simmons,
. Debtors’ Burden of Proof Brief [ECF No. 936] ¶ 4.
.
. Id.
. In re Margaux City Lights Partners, Ltd.,
. The Internal Revenue Code imposes obligations on U.S. taxpayers to report certain information about certain foreign business en-tides that they control. The failure to timely file these information returns on, as relevant here, Forms 3520, 3520-A, and 5471, results in the imposition of penalties for the taxpayer's failure to file the required form. See pp. 550-76, infra.
.See, e.g., Tr. Trans. 627:7-628:2 (Evan), 632:3-628:16 (Evan), 1515:14-1519:1 (Laurie), 1565:21-1566:13 (Laurie), 2141:13-2142:15 (Hennington), 2185:4-2192:6 (Hennington).
. See pp. 385-86, infra.
. See pp. 475-513, infra.
. See, e.g., Debtors’ Post-Trial Brief [ECF No. 1118] at 51-87.
. Raleigh,
. While the Court acknowledges that the parties have stipulated to the amount of the income tax deficiencies, thus mooting the burden of proof dispute as to these deficiencies, this analysis would have applied to them if the dispute remained live.
. Helvering v. Taylor,
. Yoon v. C.I.R.,
. Neilson v. U.S. (In re Olshan),
.
. Data Indus. Corp. of Texas v. I.R.S. (In re Data Indus. Corp. of Texas),
. The Court notes that the parties have not argued to the contrary.
. See Debtors’ Burden of Proof Brief [ECF No. 936] 19-22.
. 356 F,3d at 1084 (internal citations and quotations omitted).
. Portillo,
. In re Olshan,
. Id. at 1084-85.
. Portillo,
.
. Id. at 1131.
. Id.
. Id.
. Id. at 1134.
. Id. at 1133.
. Id. at 1134
. U.S. v. Janis,
. The Debtors rely upon Pearce v. C.I.R.,
. See Stobie Creek Inv., LLC v. U.S.,
. See Southgate Master Fund, LLC ex rel. Montgomery Capital Advisors, LLC v. U.S.,
. See pp, 513-50, infra.
. H.R. CONF. REP. 105-599, 241, 1998 U.S.C.C.A.N, 288, 310; see also Southgate Master Fund, L.L.C.,
.Southgate Master Fund, L.L.C.,
. See e.g., IRS Exs. 412 (fax dated July 10, 1995 from French to Buchannan stating "(pjlease dispose of this fax after reading, as there will be ample documentation as needed”) and 413 (fax dated July 10, 1995 from French to Cairns stating ‘‘[a]s with my other fax, I suggest that you dispose of this one as there will be adequate subsequent documentation of any transaction").
. Tr. Trans. 638:3-14 (Evan), 639:6-9 (Evan), 1895:12-1897:5 (Hennington).
. See p. 394 n. 261 & p. 550, infra,
. S. Rep. No. 105-174, 45,
. Tr. Trans, 1759:6-1763:25 (Cousins generally discussing his strategy for representing clients during the IRS audit process, including steps to keep the audit focused), 1794:7-1798:25 (Cousins discussing Meadows Owens’ involvement in the 2004 audit, including responses to IRS document requests).
. Id. at 1578:10-1583:4 (Herrick).
. Brinkley,
. See 26 U.S.C. § 7454(a) ("In any proceeding involving the issue whether the petitioner has been guilty of fraud with intent to evade tax, the burden of proof in respect of such issue shall be upon the Secretary.''); Tax Court Rule 142(b) ("In any case involving the issue of fraud with intent to evade tax, the burden of proof in respect of that issue is on the respondent, and that burden of proof is to be carried by clear and convincing evidence.”).
. See, e.g., Estate of Lisle v. C.I.R.,
. See, e.g., Maciel v. C.I.R.,
. 26 U.S.C. § 7454(a); Putnam v. C.I.R.,
. See Carreon,
. Brown v. C.I.R.,
. 26 U.S.C. § 6663(b); cf. Toussaint,
. 26-U.S.C. § 6663(c).
. Debtors’ Pre-Trial Brief [ECF No. 1015] ¶ 138 ("The IRS has the burden of proving exceptions to the general limitations period. To meet this burden, the IRS must, again, satisfy the two-prong fraud test for each year. Thus, the IRS again must prove (1) that the Wylys underpaid their tax for that year, and (2) that some part of that underpayment , for that year was due to intentional wrongdoing with the specific purpose to evade a tax believed to be owing.” (internal quotation marks omitted)); IRS’ Pre-Trial Brief [ECF No. 1018] at 3 (“The United States asserts that the statute of limitations for the income and gift tax periods at issue is open due to the fact that the Wylys committed civil tax fraud.”); see Jacoby v. C.I.R.,
. 26 U.S.C. § 7491(c); accord McLauchlan v. C.I.R.,
. 26 U.S.C. § 6664(c)(1) provides that "[n]o penalty shall be imposed under section 6662 or 6663 with respect to any portion of „ an underpayment if it is shown that there was a reasonable cause for such portion and that . the taxpayer acted in good faith with respect to such portion.”
. Id. at § 6677(d) provides that '‘[n]o penalty shall be imposed by this section on any failure which is shown to be due to reasonable cause and not due to willful neglect. The fact that a foreign jurisdiction would impose a civil or criminal penalty on the taxpayer (or any other person) for disclosing the required information is not reasonable cause.”
. Id. at § 6038(c)(4)(B) provides that ”[f]or purposes of this subsection and subsection-(b), the time prescribed under paragraph (2) of subsection (a) to furnish information (and the beginning of the 90-day period after notice by the Secretary) shall be treated as being not earlier than the last day on which (as shown to the satisfaction of the Secretary) reasonable cause existed for failure to furnish such information.”
. See Moore v. U.S.,
. Klamath Strategic Inv. Fund ex rel. St. Croix Ventures v. U.S.,
. See CNT Investors, LLC v. C.I.R.,
. See 26 U.S.C. § 6013(d)(3) ("if a joint return is made, the tax shall be computed on the aggregate income and the liability with respect to the tax shall be joint and several.”); Cheshire v. C.I.R.,
. Cheshire,
. 26 U.S.C. § 6015; Cheshire,
. 26 U.S.C. § 6015(c)(1) (referring to subsection (d) for instructions on how to calculate this separate amount); Cheshire,
. Cheshire,
. Hollimon v. C.I.R.,
. Richard v. C.I.R.,
. Given the SDNY Court's determinations that the relevant IOM trusts were grantor trusts to Sam and Charles, and subject to (i) that decision being affirmed on appeal, and (ii) this Court’s decision to apply collateral estoppel effect to that determination not being
. Gagliardi v. U.S.,
. That Sam loves his family, and vice versa, is obvious. The same is true for Dee. Throughout trial, the courtroom has been filled with a combination, albeit sometimes different combinations, of the Debtors’ children and perhaps grandchildren. Two of Sam’s children testified at trial, Evan and Laurie, and their love and respect for their father was clear. It is also clear that Sam has instilled in his children the importance of family remaining close through family trips, periodic but regular family meetings, a focus of which is simply staying in touch and letting each other know what is going on in their respective lives, and the like. Dee’s son-in-law, Donnie Miller, who is married to Dee’s eldest daughter, Martha, and who is the executor of Charles’ probate estate, also testified at trial and it is clear that Donnie was close to Charles and is close to Dee.
.Sam told a story of malting a modest and innocent mistake on an early tax return he filed which taught him that the tax laws were complicated and that he should hire professionals to assist him in complying with them, which he has done ever since. The mistake there cost him $134. Tr. Tran. 379:5-388:1; 694:4-1 l(Sam).
. As used here “wishes” is a term of art and much evidence will be discussed throughout this Memorandum Opinion about how Sam and Charles made their "wishes” known to the trustees of the IOM trusts, who then implemented those "wishes” even when sound business judgment might have suggested it was imprudent to do so.
. Collateral Estoppel No. 43; see also IRS Exs. 396 (February 2, 2004 audit letter from the IRS to Dee and Charles referencing the transfer of stock options to foreign trusts), 380 (email dated February 3, 2004 from Hen-nington to Boucher and Pulman stating "Sam really wants us to explore what happens if he is not a U.S. citizen — we can discuss tomorrow, I just did not want to forget.”), 381 and 382 (internal Meadows Owens memoranda dated February 4 and 28, 2004, respectively, analyzing taxation of expatriates); ,Tr. Trans. 1018:17-1025:3(Sam).
. Cf. Richardson v. C.I.R.,
. Although the IRS claimed one during its closing argument through a misstatement of what eliminations on a consolidated financial statement mean.
. See Richardson,
. See, e.g., Estate of Trompeter v. C.I.R.,
. See Richardson v. C.I.R.,
. Prowse,
. 26 U.S.C. § 6662(b)(6) states that: “[a]ny disallowance of claimed tax benefits by reason of a transaction lacking economic substance (within the meaning of section 7701 (o)) or failing to meet the requirements of any similar rule of law.”
. The Court does not accept the Debtors’ argument that reliance on the advice of counsel can negate fraudulent intent as a matter of law if there is clear and convincing circumstantial evidence of sufficient badges of fraud to prove fraudulent intent indirectly. If the Debtors' argument were true, there would be no need for the reliance on advice of counsel defense set forth in the statute. That reliance would simply be used to negate fraudulent intent as a matter of law as the Debtors assert here, precluding the IRS from carrying its burden of proof in every such case.
. Almost all of the badges of fraud found applicable to Sam are equally applicable to Charles since his actions offshore are virtually in lockstep with Sam's actions. Although Charles’ probate estate is not a formal party to the Motions, its counsel was present throughout the trial as was its executor, Donnie Miller, after he provided this Court with his testimony and was released from the rule. Because Dee and Charles filed joint tax returns until his death in 2011, and because Dee asks this Court to determine her liability to the IRS during those joint return years and thereafter, the Court has concluded that it must decide if Charles committed tax fraud for at least two reasons: (i) to decide if the statute of limitations on those years (1992— 2011) remains open given the IRS’ assertion of tax fraud against Dee and Charles, and (ii) to decide the extent to which Dee participated in Charles’ alleged fraud.
. See Niedringhaus,
. The other "usual” badges of fraud are simply not present here. Specifically, there is no credible evidence in the record that the Wylys (i) failed to keep adequate records or kept a double set of books and records, (ii) failed to file tax returns or make estimated tax payments, (iii) engaged in criminal activities, and/or (iv) dealt in cash. The fact that these badges of fraud are not present supports a finding of no fraudulent intent. However, as the case law makes clear, the use of badges of fraud is not a simple process of counting up the badges and seeing how many are on each side of the fraud or no fraud equation. Rather, the presence of several badges suggesting fraudulent intent can outweigh those that do not. Cf. Sanchez v. C.I.R.,
. Joint Stipulations ¶ 18.
. See pp. 513-50, infra.
. Joint Stipulations ¶ 19.
. Joint Ex. 1 (Trust Agreement of the Bulldog Non-Grantor Trust) ¶ 5.9(a) (stating the trustee shall not "[k]knowingly take any action or do any act which may cause this Trust to become a grantor trust for United States income tax purposes.”).
. Joint Stipulations ¶ 19-.
. Joint Ex. 1 ¶¶ 1(a), 5.2(a) & Schedule A.
. Joint Stipulations ¶ 21.
. Id. ¶ 22.
. Joint Ex. 2 (Trust Agreement of the Lake Providence International Trust) ¶ 5.9(a) (stating the trustee shall not "[k]knowingly take any action or do any act which may cause this Trust to become a grantor trust for United States income tax purposes."),
. Joint Stipulations ¶ 22.
. Joint Ex. 2 ¶¶ 1(a), 5.2(a) & Schedule A.
. Joint Stipulations ¶ 24.
. Id. 1125,
. Joint Ex. 3 (Trust Agreement of Delhi International Trust) ¶ 5.9(a) (stating the trustee shall not "[k]knowingly take any action or do any act which may cause this Trust to become a grantor trust for United States income tax purposes.”).
. Joint Stipulations ¶ 25.
. Joint Ex. 3 ¶¶ 1(a), 5.2(a) & Schedule A,
. Joint Stipulations ¶ 27.
. /d. ¶ 28, Joint Ex. 4.
. SEC Trial Tr.. 3751:24-3752:4, 3752:15-18 (French); IRS Ex. 806 at WYLY-SEC00010968 (February 16, 1994 memorandum from Lubar to French "Re: Foreign Trusts" in which Lubar states that trusts settled by nonresident aliens — i.e., King and Cairns — “will be ‘grantor trusts' for all U.S. federal income tax purposes ... [but] because the Grantor [King and/or Cairns] is a nonresident alien as to the United States ..., the Grantor will have no actual U.S. tax liability or obligation to file a U.S. income tax or information return.”).
. Joint Exs. 4 ¶ l(2)(e) & Schedule 3 (SWY-LY053814), 5, 6, 8, and 10.
. Joint Stipulations ¶ 36. The other corporations wholly owned by Bessie IOM Trust are Mi Casa Limited (IOM), Cottonwood I Limited (IOM), Cottonwood II Limited (IOM), Spitting Lion Limited (IOM), and Rosemary’s Circle R Ranch Limited (IOM).
, Tr. Trans, 2091:6-2092:19 (Hennington). That the liquidation occurred in 2006 is reflected in the demonstrative exhibits submitted by the parties. See Memorandum Opinion Exhibits D-G. The charts attached to this Memorandum Opinion are, for the most part, agreed demonstrative exhibits. Although the Debtors and the IRS submitted competing charts regarding the Cottonwood Ventures properties and Stargate Horse Farm, the exhibits agreed as to the basic ownership structure of the properties, which is the purpose for which they are being used here.
. Joint Stipulations ¶ 43.
. See Memorandum Opinion Exhibit D.
. Joint Stipulations ¶ 44.
. See Memorandum Opinion Exhibit E.
. Joint Stipulations ¶ 45.
. See Memorandum Opinion Exhibit F.
. Joint Stipulations ¶ 46.
. Id.
. See Memorandum Opinion Exhibit G.
. Joint Stipulations ¶ 47.
. Id.
. Id.
. See Memorandum Opinion Exhibit H.
. Joint Stipulations ¶ 48, Joint Ex, 17.
. SEC Trial Tr. 3751:24-3752:4, 3752:15-18 (French); IRS Ex. 806 at WYLY-SEC00010968 (February 16, 1994 memorandum from Lubar to French "Re: Foreign Trusts” in which Lubar states opines that trusts settled by nonresident aliens — i.e., King and Cairns — "will be 'grantor trusts’ for all U.S. federal income tax purposes ... [but] because the Grantor [King and/or Cairns] is a nonresident alien as to the United States ..., the Grantor will have no actual U.S. tax liability or obligation to file a U.S. income tax or information return.”).
. Joint Exs. 17 ¶ l(2)(e) & Schedule 3 (SWYLY053 8 60), 19, 20, 21, and 23.
. Joint Stipulations ¶ 56.
. See Memorandum Opinion Exhibit B. The date Relish Limited (IOM) was formed is not in the record.
. Joint Stipulations ¶ 57.
. Id.
. Id.
. Joint Ex. 25 ¶ l(2)(f) & Schedule 3 (SWY-LY001310).
. Joint Stipulations t 60.
. Id.
. Id.
. Joint Ex. 26 ¶ l(2)(f) & Schedule 3 (SWY-LY053892).
. Joint Stipulations ¶ 62.
. Id.
. Id.
. Joint Ex. 27 ¶ l(2)(f) & Schedule 3 (SWY-LY00887).
. Joint Stipulations ¶ 64.
. Id,
. Joint Ex. 28 ¶ l(2)(f) & Schedule 3 (SWY-LY000942).
. Joint Stipulations ¶ 75.
. Joint Ex. 35 (Trust Agreement of Pitkin Non-Grantor Trust) ¶ 5.9(a) (stating the trustee shall not "[k]knowingly take any action or do any act which may cause this Trust to become a grantor trust for United States income tax purposes.”),
. Joint Stipulations ¶ 75.
. Joint Ex. 35 ¶¶ 1(a) & Schedule A at § 2.
. Joint Stipulations ¶ 77.
. Id. ¶ 78.
. Joint Ex. 36 (Trust Agreement of the Lake Providence International Trust); id. at ¶ 5.9(a) (stating the trustee shall not "[k]knowingly take any action or do any act which may cause this Trust to become' a grantor trust for United States income tax purposes.”).
. Joint Stipulations ¶ 78.
. Joint Ex. 36 ¶¶ 1(a) & Schedule A at § 2.
. Joint Stipulations ¶ 80.
. Id, 1181, Joint Ex. 37.
. SEC Trial Tr. 3751:24-3752:4, 3752:15-18 (French); IRS Ex. 806 at WYLY-SEC00010968 (February 16, 1994 memorandum from Lubar to French "Re: Foreign Trusts” in which Lubar states .opines that trusts settled by nonresident aliens — i.e., King and Cairns — "will be 'grantor trusts’ for all U.S. federal income tax purposes ... [but] because the Grantor [King and/or Cairns] is a nonresident alien as to the United States., the Grantor will have no actual U.S. tax liability or obligation to file a U.S. income tax or information return.”).
. Joint Exs. 37 ¶ l(2)(e) & Schedule 3 (SWYLY016442), 38, 40, and 41.
. Joint Stipulations ¶ 87.
. Joint Stipulations ¶ 88, Joint Ex. 42.
. SEC Trial Tr. 3751:24-3752:4, 3752:15-18 (French); see IRS Ex. 806 at WYLY-SEC00010968 (memorandum to French dated February 16, 2004 in which Lubar opines that trusts settled by nonresident aliens — i.e., King and Cairns — “will be ‘grantor trusts’ for all U.S. federal income tax purposes ... [but] because the Grantor [King and/or Cairns] is a nonresident alien as to the-United States., the Grantor will have no actual U.S. tax liability or obligation to file a U.S. income tax or information return.”).
. Joint Exs. 42 ¶ l(2)(e) & Schedule 3 (SWYLY000763), 44, and 46.
. Joint Stipulations ¶ 94.
. Id. § 95.
. Id.
. Joint Ex. 48 ¶ l(2)(f) & Schedule 3 (SWY-LY000252).
. Joint Stipulations ¶ 98.
. Id.
. Joint Ex. 49 ¶ l(2)(f) & Schedule 3 (SWY-LY000183).
. Joint Stipulations ¶ 100.
. Joint Ex. 50 ¶ l(2)(f) & Schedule 3 (SECI0017268).
. Joint Stipulations 11119; Joint Ex. 58 (Private Annuity Agreement) § 3.1 ("The parties hereby agree that there is and shall be no
. Joint Stipulations ¶ 119; Lubar Depo, Tr. 39:7-40:5
. Id. ¶¶ 21, 119.
. Id. Ml 121, 123, 125, 127, and 129. See also Wyly Ex. B.
. Although certain annuity transactions were initiated in late December 2015, this Memorandum Opinion classifies them as part of the 1996 annuity transactions for ease of reference.
. Joint Stipulations ¶¶ 131, 133, 137, 139, and 141. See also Wyly Ex. B.
. Joint Stipulations ¶¶ 145, 147, 149, and 151.
. Id. ¶¶ 153, 155, 157, and 159.
. See Joint Exs. 59, 61, 63, 65, 67, and 69, whereby Sam deferred annuity payments scheduled to commence on his 65th birthday to his 70th birthday, and 71, 73, 75, 77, and 79, whereby Sam deferred annuity payments scheduled to commence on his 68th birthday to his 73 rd birthday. Although the record reflects that Sam entered into six annuity transactions in each of the relevant years, the record does not contain the Private Annuity Agreement or an Amendment to Private Annuity Agreement related to Yurta Faf Limited (IOM).
. Joint Stipulations ¶ 175 (annuity payments by year); Joint Exs. 58-79 (Annuity Agreements and Amendments to Annuity Agreements).
. See Joint Exs. 81, 82, and 85, whereby Charles deferred annuity payments scheduled to commence on his 65th birthday to his 70th
. Joint Stipulations 11173 (annuity payments by year); Joint Exs. 80-95 (Annuity Agreements and Amendments to Annuity Agreements). Then, beginning in late 1999, Dee' and Charles undertook a further highly complicated transaction in which all of the annuity agreements they had entered into which were held by an IOM corporation were transferred to Stargate Investments, Ltd, a Texas limited partnership (“Stargate Investments (Texas)”). A chart prepared by the parties depicting this transaction is attached as Exhibit K to this Memorandum Opinion. The evidentiary record is largely silent as to the reasons for the complexity of this further transaction. To date, in exchange for approximately $55 million worth of options, Dee and Charles have received — and paid tax on — approximately $112 million in annuity payments. As noted previously, Charles died in the summer of 2011, after which annuity payments on his life ceased. Dee continues to receive some annuity payments. More precisely, Stargate Investments (Texas) received all of the annuity payments, but Dee and Charles reported all of the annuity payments received by Stargate Investments (Texas) as ordinary income and as self-employment income on their joint federal income tax returns for the 2003 through 2011 tax years. Dee reported all of the annuity payments received by Stargate Investments (Texas) as ordinary income and as self-employment income on her individual federal income tax returns for 2012 and 2013. See Joint Stipulations §§ 161-162, 173, 174.
. Joint Stipulations ¶ 175.
. These corporations are (i) Tensas Limited (IOM), of which Sam forgave $14,913,153.13 in annuity payments, (ii) East Baton Rouge Limited (IOM), of which Sam forgave $20,947,937.97 in annuity payments, and (iii) East Carrol Limited (IOM), of which Sam forgave $25,111,130.26 in annuity payments.
As to Tensas Limited (IOM), see IRS Ex. 1131 at 582 (letter agreement whereby Sam agrees to accept Tensas Limited (IOM)’s assets valued at $2,068,000 in forgiveness of all past due annuily payments totaling $5,403,975 in principal, plus $787,742,13 in interest, and all future annuity payments) and IRS Ex, 1132 at 1495 (Tensas Limited (IOM)’s unaudited financial statement valuing future annuity payments owing to Sam, prior to forgiveness, at $10,789,436).
As to East Baton Rouge Limited (IOM), see IRS Ex. 1135 at 855 (letter agreement whereby Sam agrees to accept East Baton Rouge Limited (IOM)’s assets valued at $1,987,646 in forgiveness of all past due annuity payments totaling $3,416,187, plus interest of $252,553.97, and all future annuity payments) and IRS Ex. 1136 at 527 (East Baton Rouge Limited (IOM)’s unaudited financial statements valuing future annuity payments owing to Sam, prior to forgiveness, at $19,266,843). As to East Carrol Limited (IOM), see IRS Ex. 1134 at 4427 (letter agreement whereby Sam agrees to accept East Carrol Limited (IOM)’s assets valued at $1,283,807.74 in forgiveness of all past due annuity payments totaling $3,142,095 and all future annuity payments) and IRS Ex. 1133 at 607 (East Carrol Limited (IOM)’s unaudited financial statements valuing future annuity payments owing to Sam, prior to forgiveness, at $23,252,843). See Tr. Trans. 2647:23-267 l:70(Sam).
. See Amended Bankruptcy Schedule B, Exhibit B-16 [ECF No. 472] at p. 55 of 94. However, at trial, Sam testified he was not expecting any further payments from those entities at all. Tr. Trans. 2941:l-8(Sam). See also pp. 431-41, infra.
. IRS Ex. 96 at WYLYSECO1112402 (memorandum dated June 20, 2003 from Henning-ton and Boucher to, among others, Sam and Charles).
. Tr. Trans. 2671:3-7(Sam) ("Q. And the funds in the offshore system, including East Carroll, Tensas, and East Baton Rouge, funds were spent at your direction to buy homes, art, and invest in Wyly-related businesses. Correct? A. That sounds — that sounds correct.”).
. As will be further discussed, the IRS contends that the record supports a finding that the Wylys never intended for the annuities to be paid. According to the IRS, the Wylys didn't need for the money to come back to the United States through annuity payments that would be taxed to them as ordinary income when received, after they and their lawyers had devised complicated structures that enabled the family to enjoy the benefits of their offshore wealth in the United States tax-free. See pp. 423-31, infra.
. The Nevada entities were used to avoid payment of excise taxes on the transfers of the options and warrants. See Tr. .Trans. 1203:2-11) (Chatzky) ("the primary reason why the Nevada corporation was used is because it was believed ... that if a foreign corporation issued an annuity, that there would be an excise tax imposed on the foreign corporation in the amount of 1 percent of the consideration for the annuity. Subsequent research showed that that wasn’t the case.”). While the Court is not troubled by the use of a Nevada corporation to avoid excise tax, the use of so many and the reason that so many were used — i.e., to attempt to avoid SEC reporting requirements by keeping each entity’s ownership below the required reporting threshold as discussed infra at pp. 407-13 — is more problematic and indicative of fraud.
. Tr. Trans. 1269:20-25 (Chatzky).
. See pp. 407-13, infra.
. See pp. 513-36, infra.
. Joint Stipulations ¶ 36.
. IdA 87.
. See, e.g., Tr. Trans. 934:1-14 (Evan), 1561:11-1563:22 (Laurie), 2259:14-2262:6 (Hennington); Wyly Exs. QF (Possession Agreement dated April 2, 2004 between Laurie and her husband, on the one hand, and Audubon Asset Limited (IOM), on the other, permitting Laurie to hang various pieces of art, including Audubon plates and a Picasso painting, in her home); IRS Exs. 20, 22, 24, and 25 (invoices detailing substantial amounts of jewelry, art, antiques, and home furnishings purchased by Soulieana Limited (IOM) for use by Dee and Charles); IRS Ex, 21 at WYLYSEC00130636 (fax coversheet from Amy Browning of the Wyly family office to Huntsman Gallery directing that invoices for purchases by Dee be issued to Soulieana Limited (IOM) and that ‘‘[t]he Wyly name should not be noted on the invoices”); IRS Ex. 203 at 145098 (letter dated December 1, 2000 from Trident Trust to Man & Partners discussing drafting of Possession Agreements for assets owned by Soulieana Limited (IOM) and used by Dee and Charles, explaining that: “[w]e should appreciate your assistance in the preparation-of a Possession Agreement Letter in respect of personal chattels, owned by [Soulieana Limited (IOM) ], presently in the possession of individuals on an informal basis. * * * The schedule of chattels will be extensive and comprise items of antiques, furniture, paintings and prints, silverware, glassware, porcelain and ceramics, miscellaneous objects of art and jewelry. The value in total is in excess of $4 million.”). As reflected on IRS Ex. 444, sometime around December 2000, Charles agreed to purchase from Soul-ieana Limited (IOM) all items it purchased on his and Dee’s behalf with a cost of $10,000 or less, which totaled “around $381K,” and setting a minimum cost threshold of $10,000 for future purchases by Soulieana Limited (IOM). IRS Ex. 444 at SEC/ITC0104002; Tr. Trans. 2386:18-2390:18 (Hennington discussing Charles' purchase of the assets from Souliea-na Limited (IOM)).
. See pp. 446-47 n. 573-75, infra.
. Collateral Estoppel No. 1; Joint Stipulations ¶¶ 18-74 (Sam IOM entities), 75-109 (Charles IOM entities), 68 (Sam protectors), 104 (Charles protectors); SEC Tr. Trans. 1731:24-1732:1 (French discussing being a protector with Robertson); 1736:9-1737:15 (French testifying that the IOM trustees never refused a direction), 294:17-23 (Robertson testifying she does not recall an instance where an IOM trustee refused a recommendation), 555:3-8 (Robertson testifying that no material securities transactions were initiated without 'Sam’s or Charles' input), 997:5-10 (Boucher testifying all securities transactions were initiated by Charles or Sam), 1114:20-23 (Boucher testifying she does not recall a single instance between 1995 and 2005 where a trustee refused to implement a recommendation).
. Collateral Estoppel No. 2; Joint Stipulations ¶¶ 3-4, 8-10, and 13-14, (discussing positions the Wylys held with various companies) and 119-176 (discussing annuity and stock transactions); Tr. Trans. 1692:6— 1694:24 (Sam testifying that trust holdings were kept below 5% to avoid SEC filing requirements), 1696:7-1697:5 (Sam testifying that it wasn’t until 2005, and after the SEC investigation began, that he and Charles filed documents with the SEC disclosing that either of them beneficially owned securities in Michaels Stores, Sterling Software, Sterling Commerce, or Scottish Re), 1914:4-1915:8 (Hennington discussing compensatory nature of the options transferred to the IOM corporations).
. Collateral Estoppel No. 3.
. Collateral Estoppel No. 4.
. Collateral Estoppel No. 5; SEC Tr. Trans. 156:25-157:7 (Robertson); Robertson Depo. Tr. 76:19-77:2; IRS Ex. 85 (June 12, 1991 memorandum from Robertson to Sam, Charles, Evan, French, and Ethel Ketter, in-house CPA for the Wyly family office, discussing Tedder’s seminar on asset protection and tax deferral); Tr. Trans. 696:23-627:16 (Sam, however, testified that he did not attend the New Orleans conference); SEC Tr. Trans. 168:2-12 (Robertson testifying that she attended the New Orleans seminar along with Sam, Charles, and French); SEC Tr. Trans. 1716:9-1718:8 (French testifying regarding the various seminars and meetings); Tr. Trans. 1050:19-1059:11 (Sam testifying regarding the various seminars and meetings); IRS Ex. 525 (written information Sam received from Tedder titled "An Overview of Asset Protection Estate and Income Tax Reduction Using Domestic and International Structures”).
. Collateral Estoppel No. 6; Tr. Trans. 1050:19-1051:16(Sam), 1052:9-1059:ll(Sam); SEC Tr. Trans. 1719:3-17 (French); IRS Ex. 525 (written information Sam received from Tedder titled “An Overview of Asset Protection Estate and Income Tax Reduction Using Domestic and International Structures”).
. Collateral Estoppel No. 7; IRS Exs. 130 (November 11, 199Í memorandum from French to Sam discussing tax benefits of foreign trusts), 93 (tax savings chart reflecting a fax date of November 1, 1996 and bearing the notation "Sam likes the #'s!”), 85 (June 12, 1991 communication from Robertson to Sam, Charles, and others) at SEC100150261 (listing the six "goals” of the Tedder tax scheme, three of which are to avoid taxes — "(1) Never pay probate.... (2) Whenever possible eliminate inheritance tax_ (3) Wherever possible reduce income tax — both domestically and foreign.”).
. Collateral Estoppel No. 8; SEC Tr. Trans. 1719:7-1721:6 (French); IRS Ex. 1199 ¶ 9(p.7) (Annex A, Admissions of Defendant Michael C. French).
. Collateral Estoppel No. 9.
. Collateral Estoppel No. 10.
. Collateral Estoppel No. 11; Tr. Trans. 727:5-14(Sam); IRS Ex. 86 (email from Robertson to Evan dated November 3, 2000 and stating "[r]emember that it is critical from a U.S. tax standpoint that there is no appear
. While this may appear to be a formatting error in this Memorandum Opinion, it is not. Rather, when the IRS submitted its proposed collateral estoppel findings from the SEC Action, it submitted findings made by the SDNY Court in footnotes as well as in the body of the court’s opinion. So, footnote 91 as quoted here is footnote 91 in the SDNY Court’s opinion, which is Collateral Estoppel No. 12 on Exhibit A to this Memorandum Opinion. Anytime a footnote is quoted in this body of this Memorandum Opinion, it is a footnote finding of the SDNY Court in the SEC Action, to which this Court has given collateral estop-pel effect.
. Collateral Estoppel No. 12; Tr. Trans. 727:5-14(Sam); IRS Ex. 86 (November 3, 2000 email from Boucher to Evan).
. Collateral Estoppel No. 13; SEC Tr, Trans. 246:11-248:2 (Robertson testifying regarding tracking ownership of stock among trust management companies, transferring stock between companies, and hiring new trust' management companies to avoid any single company owning more than 5% of the issuer which triggers mandatory reporting); accord Harris Depo. Tr. 89:6-91:10 (reading from his dictated notes from a February 14, 1996 meeting with French and Robertson held in Dallas — "[o]ne of the reasons they [the Wylys] have a variety of offshore trusts is that holdings in Sterling Software or [Sterling Commerce] held by a trust company for various trusts ... are amalgamated for SEC purposes and any trust company holding an aggregate of more than 5% of any one class of shares in a company has certain fairly onerous filing requirements with the SEC. [French and Robertson] confirmed that they were always aware of this as far as the various Wyly entities were concerned and that we need not review this, but we might just need to think about other trusts possibly holding these stocks.”). Tr. Trans. 1382:8-1384:21 (Sam being impeached with his testimony from the SEC trial that ownership levels were kept under 5% in order to avoid reporting requirements).
.Collateral Estoppel No. 14; IRS Ex. 372 (February 26, 2002 email from Hennington and Boucher to Sam) at SEC/ITC0105445 (“There needs to be a good answer to the increase in shares from what was publicly represented during the CA proxy fight. I think that those watching this will raise this
. Collateral Estoppel No. 15; IRS Ex. 372 (February 26, 2002 email from Hennington and Boucher to Sam) at SEC/ITC0105445.
. Collateral Estoppel No. 16; SEC Tr. Tran. 169:10-12 (Robertson). See, e.g., Joint Ex, 1 (Trust Agreement of the Bulldog Non-Grantor Trust) ¶¶ 1(a) (definition of "Beneficiaries”), 4.2(b), 5.2(a),
. Collateral Estoppel No. 17; SEC Tr. Tran. 169:10-12 (Robertson). See, e.g., Joint Ex. 1 (Trust Agreement of the Bulldog Non-Grantor Trust) ¶¶ 1(a) (definition of "Beneficiaries”), 4.2(b), 5.2(a).
. See p. 410 n. 376, supra.
. See p. 410 n. 377, supra.
. Tr. Trans. 547:25-548:23, 553:11-23 (Evan testifying that the Wylys "always went to Mike first,” and that "Mike would be kind of the lead, but he would bring in whatever specialist he needed. And if there wasn’t someone at Jackson Walker that could do it, then he would bring in, you know, an outside attorney.”)
. A letter agreement dated January 24, 1997 signed by Sam and French set forth "certain arrangements with respect to (i) my retention by you as legal counsel in connection with all family and family-related business activities; (ii) my interest in the investment management business ... [Maverick Fund]; and (iii) an overall guaranteed level of income that I will have going forward from various activities on behalf of your families; and certain related or associated activities.” SEC Tr. Trans. 1706:11-20 (French). The letter stated that French was retained as “legal counsel for the Wylys” because Sam "insisted” that their conversations be subject to attorney/client privilege, "whatever I did.” Id. 1706:2-10 (French). See also Tr. Trans. 699; 15-21 (Sam) ("Q. Okay. What role did Mr. French play in setting up the Isle of Man trusts? A. Well, he was the chief — chief lawyer, chief architect, who — I mean, there were others who worked on it, but he was the — I would say the leader of a team of lawyers and certified public accountants who worked on it.”), 709:1-20 (Sam explaining how French was charged to oversee and recruit the legal specialists hired to establish the trusts); Joint Stipulations ¶ 11 ("Mr. French served as primary counsel for Sam Wyly and Charles Wyly until early 2001 when the relationship was severed.”).
.Joint Stipulations ¶ 11; p. 413 n. 391, supra.
. Collateral Estoppel No. 18. These facts were established here by clear and convincing evidence with the exception of whether French was given the Lubar memorandum. While the record here is clear that Lubar discussed its contents with French, it is equivocal on whether French was actually given a copy of the memorandum in 1993. See Lubar Depo. Tr. 93:13-25 (Lubar testifying that he had discussed the issues with French, but could not remember if he provided French with a copy of the memorandum).
. Lubar Depo. Tr. 13:10-14:6, 16:11-19:5 (discussing his initial contact with French and the results of his analysis). Although the underlying memorandum was not admitted into the record here, it is .thoroughly discussed in deposition testimony given by Lubar, which was admitted into the record by agreement of the parties. See id. at 17:6-19:5, 93:5-95:18.
. Id. at 9:12-18.
. Id. at 15:4-8.
. Id. at 15:12.
. Tr. Trans. 548:13-16 (Evan discussing how French was authorized to seek out other attorneys to give advice), 549:8-22 (Evan discussing how the Wylys perceived no material difference when French moved from Jackson Walker to Jones Day in 1995 "[a]nd while the secondary attorneys might have changed ... we still looked to him [French] first as kind of our trusted counsel on who should be the best person. And he continued to find outside attorneys if there wasn't a specialist inside Jones Day that could handle the situation.”), 553:19-23 (Evan) ("And Sam was in a really good — kind of at a high level, and so if Mike needed some kind of high-level direction, he would come and ask Sam, but then, you know, Mike would go off and, you know, handle the details.”), 709:1-20 (Sam explaining how French was charged to oversee and recruit the legal specialists hired to establish the 1994 and 1995 trusts); Joint Stipulations ¶ 11 ("Mr. French served as primary counsel for Sam Wyly and Charles Wyly until early 2001 when the relationship was severed.”).
. See pp. 417-23, infra, for a discussion of imputation.
. As discussed previously in this Memorandum Opinion, Lubar was consulted again in 2003 — this time by Hennington and Boucher acting as Sam’s and Charles’ agents — and he reconfirmed his 1993 conclusions then after reanalyzing the legal issues. See pp. 371-72, supra.
.Collateral Estoppel No. 19. Lubar Depo. Tr. 27:4-23; IRS Ex. 806 (February 15, 1994 memorandum from Lubar to French regarding "Tax Consequences of Grantor Trusts) at SYLYSEC00010967-0968.
. Collateral Estoppel No. 20; Joint Exs. 4 (Deed of Settlement, Bessie IOM Trust), 37 (Deed of Settlement, Tyler IOM Trust); SEC Tr, Trans. 3755:10-3757:22 (French testifying regarding King’s failure to fund); IRS Exs. 214 (November 16, 1995 fax from French to Buchanan regarding Boucher’s inability to find any records that King ever funded the Bessie IOM Trust, the Tyler IOM Trust, and the South Madison IOM Trust, and noting similar issues with the La Fourche IOM Trust and Red Mountain IOM Trust), 178 at 02517 (November 26, 1995 faxes from Buchanan to French regarding funding issues, stating the Bessie IOM Trust and Tyler IOM Trust had each been funded with "a factual Dollar bill”).
. Collateral Estoppel No. 21.
. Collateral Estoppel No. 22; Joint Exs. 17 (Deed of Settlement, La Fourche IOM Trust), 42 (Deed of Settlement, Red Mountain IOM Trust); IRS Ex. 414 (letter from Cairns to Sam dated July 18, 1995); Cairns Depo. Tr. 43:3-18 (French prepared the letter), 46:5-8; 56:9-12 (discussing Cairns’ failure to fund the trusts with $25,000), 46:18-47:4; 158:6-7 (Cairn’s admitting he did not know Sam and that the letter was provided. to him by French); Joint Stipulations ¶¶ 66 and 102 (showing that Cairn’s company, Wychwood Trust Limited, served as trustee for Delhi IOM Trust, La Fourche IOM Trust, and Red Mountain IOM Trust).
.Collateral Estoppel No. 23; p. 414 n. 404, supra (as to Cairns); p. 414 n. 402, supra (as to King); Tr. Trans. 583:23-584:7 (Evan testifying that King was a stockbroker who had done some, but not a. lot, of business with Maverick).
. Collateral Estoppel No. 24; Joint Stipulations ¶¶ 66 and 102 (showing that Cairn’s company, Wychwood Trust Limited, served as trustee for Delhi IOM Trust, La Fourche IOM Trust, and Red Mountain IOM Trust); Cairns Depo. Tr. 46:5-8; 56:9-12 (discussing his failure to fund the trusts with $25,000); IRS Exs. 214 (November 16, 1995 fax from French to Buchanan regarding Boucher’s inabilily to find any records that King ever funded the Bessie IOM Trust, the Tyler IOM Trust, and the South Madison IOM Trust, and noting similar issues with the La Fourche IOM Trust and Red Mountain IOM Trust) and 178 at 02517 (November 26, 1995 faxes from Buchanan to French regarding funding issues, stating the Bessie IOM Trust and Tyler IOM Trust had each been funded with "a factual Dollar bill”); Tr. Trans. 583:23-584:7 (Evan testifying that King was a stockbroker who had previously done some, but not a lot, of business with Maverick); SEC Tr. Trans. 3753:5-14 (French testifying that he believed that BCing had made substantial money previously dealing with the Wylys in South African bonds).
. Tr. Trans. 709:1-20 (Sam explaining how French was charged to oversee the legal specialists hired to establish the trusts), 703:11 — 25 (Sam explaining that "he [French] was sort of the coordinator or the commander of the lawyers who — who worked on it” while Sam considered himself more the "leader of the companies.”). Sam’s approach of letting French handle his transactions was confirmed by Evan. See id. 548:13-16 (Evan discussing how French would seek out other attorneys to give advice — “So Mike would be kind of the lead, but he would bring in whatever specialist he needed. And if there wasn't someone at Jackson Walker that could do it, then he would bring in, you know, an outside attorney.”), 549:14-22 (Evan discussing how the Wylys perceived no material difference when French moved from Jackson Walker to Jones Day in 1995 "[a]nd while the secondary attorneys might have changed ... we still looked to him [French] first as kind of our trusted counsel on who should be the best person. And he continued to find outside attorneys if there wasn’t a specialist inside Jones Day that could handle the situation.”), 553:19-23 (Evan) (“And Sam was in a really good — kind of at a high level, and so if Mike needed some kind of high-level direction, he would come and ask Sam, but then, you know, Mike would go off and, you know, handle the details.”).
. Davis-Lynch, Inc. v. Asgard Tech., LLC,
. Welch,
. Joint Stipulations ¶ 11; p. 417 n.. 407, supra.
. Tr. Trans. 570:4-11 (Evan).
. Id. at 587:12-588:3 (Evan).
. Id. at 703:4-25(Sam).
. Annotation, Imputing Agent’s Knowledge to Principal,
. Restatement (Third) of Agency § 5.03 (2006).
. Minter v. Great American Ins. Co. of New York,
. Victory v. State,
. Preston Farm & Ranch Supply, Inc. v. Bio-Zyme Enterprises,
. See, e.g., Standard Sav. & Loan Ass'n v. Fitts,
. Debtors' Post-Trial Reply [ECF No. 1121] at 16 (emphasis in original),
. Debtors’ Post-Trial Brief [ECF No. 1117] at 15,
. Id.
.
.
. Henry,
.
. Id. at 88.
.
. Debtors’ Post-Trial Brief [ECF No. 1117] at 29.
. Id.
. Id. at 30.
.See Tr. Trans. 1394:16-24 (Sam testifying . that French was a securities lawyer and that "I don’t recall him [French] being concerned about tax things); SEC Tr. Trans. 3758:7-8 (French) ("I’m not the tax lawyer. I’ll take that disclaimer again.”).
. See IRS Ex. 806 at WYLYSEC00010967 (¶ 1). The facts that French told Lubar to assume were true were not true — King and Cairns had not known Sam and Charles "for a considerable period of time;” King and Cairns did not establish his respective trusts as "an entirely gratuitous act;” and Cairns did "receive consideration, reimbursement or other benefits” for settling these trusts.
. King was a stock broker that had previously done some, but not a lot, of business with Maverick. Tr. Trans. 583:23584:12 (Evan); SEC Tr. Trans, 3753:5-14 (French).
. Cairns Depo. Tr. 46:22-47:4, 158:6-7.
. See IRS Ex. 92 (letter dated July 18, 1995 from Cairns to Sam).
. Collateral Estoppel Nos. 22-24; Joint Stipulations ¶¶ 66 and 102, (showing that Cairn's company, Wychwood Trust Limited, served as trustee for Delhi IOM Trust, La Fourche IOM Trust, and Red Mountain IOM Trust).
. Tr. Trans. 583:23-584:7 (Evan).
. SEC Tr. Trans. 3753:5-14 (French).
. Tr. Trans. 549:15-19 (Evan), 789:16-20 (Evan agreeing that French was one of the Wylys' “most trusted advisors”), 1420:8-10(Sam). Joint Stipulations ¶ 11.
. IRS Ex. 1199 ¶ 26 (p. 10) (Annex A, Admissions of Defendant Michael C. French).
. IRS Ex. 364 at IOM 37827.
. Id. at IOM 37820 (emphasis in original).
. Id. at IOM 37826 (emphasis added). Recall the earlier meeting where French and Robertson instructed Webb, another IOM trustee, to deal through Boucher to keep communications offshore. See supra at pp. 373-74. The Court reasonably infers that French and Robertson had a similar conversation with all the Wyly IOM trustees when Boucher was hired, including in this instance, Buchanan.
. Although the overnight fax was from French, not Boucher.
. IRS Ex. 364 at IOM 37824-25. .
. Id. at IOM 37825.
. Id.
. Id. at IOM 37813.
. Joint Stipulations ¶ 36.
. Id. ¶ 66.
. Tr. Trans. 2037:17(Sam).
. See Notice of Funds Received from Dallas Auction Gallery Sale [ECF No. 921-1] at p, 1 of 13.
. SEC. Tr. Trans. 1004:1-3 (Boucher) (Q: Do you recall Sam Wyly joking, "Well, we'll just fire the trustees if we [sic] don’t do what they [sic] tell them? A: Yes.”).
. IRS Ex. 87 at WYLYSEC01112940 (emphasis added).
. Id.
. Id. at WYLYSEC01112942 (emphasis added).
.Id. at WYLYSEC01112941.
.This transaction will be explained more fully when analyzing the IRS’ claim that this transaction gives rise to a gift. See pp. 516— 36, infra.
. Tr. Trans. 2542:1-2543:10 (Pulman).
. Id. at 2556:14-19.
. IRS Ex. 87 at WYLYSEC01112940.
. Other Wyly family members also use the apartment and office,
. These transactions are discussed in more detail later in this Memorandum Opinion. See pp. 516-36, infra.
. Collateral Estoppel No. 26; see also IRS Ex 1245 (email chain regarding sale of 169,-000 shares of Tyco stock).
. Joint Stipulations ¶¶ 434, 437, 439, 440, and 442. Emily and Jennifer share a home on the ranch. Tr. Trans. 2187:2188:6 (Hen-nington).
.Joint Stipulations ¶¶ 378-380, 384, 387, and 410; Tr. Trans. 2184:6-2185:19 (Hen-nington). Although the Joint Stipulations state that Stargate Horse Properties, Inc. (Nevada) was the 98% owner, while Stargate Sport Horse Management LLC (Texas) was the 2% owner, the agreed demonstrative chart provided to the Court states that Stargate Horse Properties, Inc. (Nevada) was the 91.21% owner, while Stargate Sport Horse Management LLC (Texas) was the 8.79% owner. Although the Court notes this discrepancy, it is not material to its "decision.
. IRS Ex. 18 at RDE 26. ■
. Id.
. Tr. Trans. 231:1-16(Dee).
. See, e.g., IRS Ex. 20; Tr. Trans. 240:15-18(Dee).
. Like the jewelry Charles gave her, there is no evidence that Dee knew the items were paid for by an IOM corporation. The payment arrangements were taken care of by someone in the Wyly family office — in this instance Amy Browning — at Charles’ direction. Dee considers the items to be hers.
. Tr. Trans. 266:24-267:2 (Dee confirming that Ms. Browning worked in the Wyly family office).
. IRS Ex. 21 (emphasis added).
. Tr. Trans. 262:24-263 :l-2(Dee).
. Again, without evidence that Dee knew who paid for the items. See, e.g., IRS Ex. 25. The record contains many other examples where Soulieana Limited (IOM) paid for personal property used by the Wyly family. See IRS Exs. 22 (February 22, 1997 invoice from Huntsman Gallery of Fine Art indicating that several works were sold to Dee but invoiced to Soulieana Limited (IOM)), 433 (May 29, 1997 fax and attached invoices, sent to Buchanan from Boucher, stating that "[t]he protectors for Tyler recommend that Soulieana acquire the following art work ... Bank wiring instructions are as follows.”), 1240 (January 22, 1997 handwritten note to Buchanan from Robertson stating "[w]e are recommending the purchase of investment grade collectibles, antiques and art for Soulieana[.] We recommend purchases totaling approximately $3,500,000 ... Invoices and photos of all art work will be forwarded thru Michelle Boucher. The ‘collection’ will be located at 5906 Deloache, Dallas, TX.”).
. Although a signed copy of IRS Ex. 26 is not in the record, Hennington testified that the agreement or a very similar one was executed. Tr. Trans. 2267:3-6 (Hennington). See also Wyly Ex. QF (executed Possession Agreement dated April 2, 2004 permitting Laurie to possess various art, including Audubon plates and a Picasso painting purchased by Audubon Asset Limited (IOM)).
. Dee repeatedly, and credibly, testified that she was unaware of the source of the funds used to purchase the furnishings, art, and antiques in her homes. See, e.g., Tr. Trans. 264:19-20, 263:23-25, 264:12-20, 268:5-18, 270:8-15, 274:16-22, 274:17-22; 279:5-17, 281:6-14, 289:11-14. This is the same for jewelry that she considers herself the owner of. See p. 431 n. 480, infra.
.Tr. Trans. 155:3-10 (Dee testifying she and Charles moved to Highland Park in 1970), 155:16-25 (Dee and Charles moved to the house on Deloache in the mid-1970s), 158:11-14 (Dee considered herself wealthy when she lived in the Deloache house), 158:15-18 (Dee and Charles owned a home in Aspen in the 1970s), 319:16-18(Dee) (receiving jewelry after the IOM trusts were formed did not change her lifestyle), 1327:18-23 (Donnie Miller) (the family used private and charter aircraft as early as the 1960s), 1334:1-17 (Donnie Miller) (family was wealthy decades before the IOM structure was established in the 1990s, and there was no significant change in lifestyle after 1992), Wyly Exs. PX (1988 Form 1040 showing adjusted gross income- of $909,959), PY (1989 Form 1040 showing adjusted gross income of $3,388,981), QB (1990 Form 1040 showing adjusted gross income of $740,173), and PZ (Charles’ personal balance sheet as of December 31, 1991 showing total assets (at fair market value) of $57,415,111); Tr. Trans. 2141:1-9 (Hennington) (Charles and Dee's net worth exceeded $50 million in 1991, the year before the first offshore trust was settled).
. See, e.g., Tr. Trans. 231:1-16, 238:7-11, 240:15-18, 244:18-24 (Dee testifying regarding jewelry given to her by Charles, but paid for by Soulieana Limited (IOM), of which she considers herself the owner), 251:4-19 (Dee was unaware that Soulieana Limited (IOM) paid for jewelry she believes she owns).
. See Joint Exs. 58, 60, 62, 64, 66, and 68 (Sam), 86 (Dee), and 80, 83, and 84 (Charles).
. See Joint Exs. 70, 72, 74, 76, and 78(Sam) and 88, 90, 92, and 94 (Charles). Although the record reflects that Sam entered into six annuity transactions in each of the relevant years, the record does not contain the Private Annuity Agreement or an Amendment to Private Annuity Agreement related to Yurta Faf Limited (IOM).
.' Dee and Charles assigned their rights to receive annuity payments to Stargate Investments (Texas), an entity they wholly-owned and controlled. Seepp. 542-50, infra.
. Joint Stipulations ¶¶ 173-174.
. Id. ¶¶ 175-176.
. IRS Ex. 1131 at EOI-IOM-SW-0000017582.
. Id.
. Id.
. Id.
. IRS Ex. 1132 at EOI-IOM-SW-000001493, § 1.2 ("Discussions are on going with the annuitant in order to agree [to] a scheme of arrangement which would allow the remaining assets of the company to be offset against current and future obligations of the company to the annuitant so that the company can be liquidated shortly thereafter.”).
.Id. at 495.
. Sam’s testimony was in rounded amounts, and resulted in his estimate of approximately $14 million in annuity payments being forgiven by Tensas Limited (IOM). Tr. Trans. 2657:19-2658:6(Sam).
. IRS *Ex, 1135 at EOI-IOM-SW-0000013855.
. Id.
. Id.
. Id.
. IRS Ex. 1136 at EOI-IOM-SW-0000000527. Sam’s testimony was in rounded amounts, and resulted in his estimate of approximately $20.5 million in annuity payments being forgiven by East Baton Rouge Limited (IOM). Tr. Trans. 2665:18-24(Sam).
. IRS Ex. 1136 at EOI-IOM-SW-0000000526 § 1,2 (Discussions are on going with the annuitant in order to agree [to] a scheme of arrangement which would allow the remaining assets of the company to be offset against current and future obligations of the company to the annuitánt so that the company can be liquidated shortly thereafter.”).
. IRS Ex. 1134 at EOI-IOM0SW00000014427.
. Id.
. IRS Ex. 1133 at EOI-IOMOSW-0000000607 (line item "Waiver of annuity payable”).
. The Court reasonably presumes this liquidation, despite the absence of language in its financial statements similar to that found in Tensas Limited (IOM)'s and East Baton Rouge Limited (IOM)’s financial statements. Whether the company was liquidated, however, is not material to this Court’s decision,
. See, e.g., IRS Ex. 96 at WYLY-SEC011112396 (July 30, 2003 memorandum from Hennington and Boucher to Sam, Charles, Evan, and Donnie Miller discussing concerns regarding payment of upcoming annuity obligations, including: (i) ”[t]he annuity payments will bankrupt several of the IOM companies, which could bring the validity of the annuity transaction into question,” (ii) ”[a]fter a few years of payments, the companies will be left with non-liquid assets,” and (iii) "[t]he possibility of in-kind payments ,.. may call into question the validity of the transaction and the ‘arms-length’ nature of the transactions."
. IRS Ex. 1266 (October 18, 2007 Meeting Minutes, Audubon Assets Limited (IOM) regarding loans from Kaly, Orange, and Balch).
. IRS Ex. 1267 (October 18, 2007 Meeting Minutes, Moberly Limited (IOM)) §§ 2.1, 2.2, and 3.
. See SEC v. Wyly, 56 F.Supp,3d at 401 ("I presided over a jury trial on nine of the ten claims from March 31 to May 7, 2014. On May 12, 2014, the jury returned a verdict against both Sam and Charles Wyly on all nine claims.”).
. See Post-Fact Discovery Scheduling Order at 3 (Case No. 10-cv-05760 at ECF-No. 196) (setting the start of trial as Monday, March 31, 2014).
. See Amended Bankruptcy Schedule B, Exhibit B-16 [ECF No. 472] at p. 55 of 94 (listing the annuity payments and stating "no payment expected in the near term”).
. Tr. Trans. 2941:l-8(Sam).
. See IRS Ex. 1267 (meeting minutes for Moberly Limited (IOM) discussing loans from Morehouse Limited (IOM) to fund annuity payments).
. See IRS Ex. 1268 §§ 3.1-3.4 ("The Chairman [of Moberly Limited (IOM), Anna Kawa-lek] reminded the Meeting that the Company [Moberly Limited (IOM) ] had loaned funds of $26,508,820 to Greenbriar Limited [ (IOM) ] ("Greenbriar”). The Chairman adviséd that the Company had received a letter from Greenbriar enquiring as to whether the Company intended to make a formal demand for repayment of any part of the loaned funds prior to 2018. After due consideration, it is resolved — THAT the Company does not intend to make a formal demand for any part of the loan due from Greenbriar before 2018 and that the Company will write to the directors of Greenbriar to confirm this formally.”).
. IRS Ex. 1266 (October 18, 2007 meeting minutes for Audubon Asset Limited (IOM) discussing loans from various Cayman LLCs to fund annuity payments). Sam expressed no surprise that Audubon Asset Limited (IOM) needed to borrow money to make the annuity payments owing to him. Tr. Trans. 2041:ll-12(Sam) ("It’s not a surprising thing.”).
. See, e.g., Joint Stipulations ¶¶ 332, 334, and 337 (funds transferred from Audubon Asset Limited (IOM) related to the Cottonwood Ventures I property); Wyly Ex. QF (Possession Agreement dated April 2, 2004 permitting Laurie to possess various art, including Audubon plates and a Picasso painting purchased by Audubon Asset Limited (IOM)); IRS Ex. 364 (documenting circumstances surrounding purchase of Noon Day Rest by Fugue Limited (IOM) n/k/a Audubon Asset Limited (IOM)).
. IRS Ex. 1269 (Locke Limited (IOM)’s unaudited Directors' Report and Financial Statements for the Year Ended 31 December 2013) at 6 (showing a loan to Bulldog IOM Trust of $3,055,728 and to Moberly Limited (IOM) of $8,028,596).
. Id. at 7 (showing a $69,183,748 annuity obligation as of December 31, 2013).
. IRS Ex. 96.
. Id. at WYLYSEC011112396 (emphasis added).
. Joint Stipulations ¶¶ 285-286. Although the exact ownership structure was never clearly established on the record, Boucher testified that "Security Capital was established and managed by a trust company group in Cayman that was familiar with Maverick and another group of funds that the [Wyly] family had been involved with, and with Irish Trust and the Wyly group. They had an understanding and knowledge of the family group as a whole.” SEC Tr. Trans. 1075:7-11 (Boucher).
. See Tr. Trans. 2347:6-12 (Hennington testifying that Security Capital was the entity that facilitated the loans); IRS Ex. 712 (undated correspondence from Hennington to Charles discussing a loan of offshore funds to Charles — "He [Owens] is more comfortable making a loan to you from an IOM Company. To add another layer we will have the IOM Company loan to Security Capital and Security Capital will loan to you. Security Capital is a company we set up to administer these types of transactions and Michelle [Boucher] and I like having another company in the middle.”); IRS Ex. 212 (January 29, 2002 email from Boucher to Hennington titled "Security Capital loan to Sam” and stating "I had to move money around to get it in the right place to fund this. So Devotion is buying $15Million of Ranger from Sarnia, to get the money to Sarnia who will loan it to Greenbriar, who will loan it to Security Capital etc ...'”); IRS Ex. 213 (September 25, 2002 email from Hennington to Owens discussing structure of a $6 million loan from .Security Capital to Charles utilizing funds from Gorsemoor Limited (IOM), which was a , subsidiary of Tyler IOM Trust).
. SEC Tr. Trans. 1071:16-18 (Boucher); IRS Ex. 91 (chart prepared by Wyly counsel Bickel & Brewer showing "pass-through loans” involving IOM corporations and Security Capital).
. SEC Tr. Trans. 1071:22-1074:24 (Boucher).
. Id. at 1077:10-22 (Boucher) (“Q: A person on the street couldn’t just walk in to Security Capital and get a loan for their mortgage, correct.? A: No. Q: It was money that was borrowed, largely borrowed, from the Isle of Man subsidiary companies and then loaned out based on recommendations, correct? A: Of course.” See IRS Ex. 91.
. See IRS Ex. 91 (chart prepared by Wyly counsel Bickel & Brewer showing “pass-through loans” involving IOM corporations and Security Capital); Joint Stipulations
.See, e,g„ Tr. Trans.2022:19-22, 2024:19-2026:7 (Sam explaining that real estate, furnishings, art, and jewelry were purchased by IOM entities for his and his family’s use), 2671:3-7 (Sam agreeing that funds in the offshore system, including those of IOM corporations who were ultimately unable to make annuity payments, were used at Sam's direction to buy homes, art, and invest in Wyly-related businesses).
. Tr. Trans. 2929:2930:5 (Sam testifying that offshore funds were used to make investments in Wyly-related businesses through letters of wishes).
. IRS Ex. 96 at WYLYSEC01112402 (no. 1 under "other factors to consider”).
. But the Court rejects outright the argument made in closing that the elimination of the annuity payments on a consolidated Wyly family financial statement was, as was argued, the Perty Mason moment in our trial. Such eliminations are commonplace on consolidated financials and are simply immaterial to any issue before this Court in this trial.
. IRS Ex. 93 at SEC/ITC01388418.
. Tr. Trans. 3531:14-3540:10 (closing argument).
.The Court is not using the word “tracing” in a formal sense of tracking receipt of funds and expenditures of funds to the penny. It just wanted some reasonably detailed explanation of where the money went. The silence was deafening.
. Tr. Tran. 2150:1-2151:4 (Hennington); Wyly Ex. OW (Partnership Agreement for Stargate Investments, Ltd.) at Exhibit A; Joint Stipulations ¶ 161,
. Wyly Ex. OW § 2.2; Joint Stipulations ¶ 162.
. See Wyly Ex, OW at § 3.1; Caroline D. Wyly's Motion for an Order Approving the Allocation of Future Payments Made on Past-Due Annuity obligations and Providing Notice of the Sale of the Underlying Assets Related Thereto [ECF. No. 634] (hereinafter "Annuity Allocation Motion”), Order Granting Annuity Allocation Motion [ECF 721],
. See Wyly Ex. OW at Exhibit A.
. Joint Ex. 86 (Private annuity agreement entered into between Dee and Maroon Limited, a Nevada Corporation); Joint Stipulations ¶¶ 151-52, 161 (The private annuity agreement was transferred from Maroon Limited, a Nevada Corporation to Rugosa Limited (IOM), and Charles and Dee transferred all of their private annuity agreements to Stargate Investments (Texas)); Wyly Ex. OW.
. IRS Ex. 401 at CW-IDR-0000000112.
. Id. atCW-IDR-0000000131.
. Id. at CW-IDR-0000000119.
. Id.
. Id. at CW-IDR-0000000123.
. See Joint Stipulations II173.
. See IRS Ex. 401 at 119.
. Tr. Trans. 314:10-316:8(Dee).
. Id. Dee was not asked any questions about the Scheme of Arrangement on redirect.
. The parties stipulated that annuity payments were not made during certain years by at least one offshore entity on an annuity payable to Charles. See Joint Stipulations ¶ 173 (Roaring Creek Limited (IOM) did not make payments in 2005-2008).
. Computation Stipulations at Attachment A. This agreement is contingent upon (i) the SDNY Court’s determination of foreign grant- or trust status being affirmed on appeal, which appeal is currently pending before the Second Circuit Court of Appeals, and/or (ii) this Court’s collateral estoppel decision being affirmed on appeal, assuming such an appeal is taken.
. Id. at Attachment B. This agreement is subject to the same contingencies as stated in the immediately preceding footnote.
. Even without this badge of fraud, the IRS has carried its burden of proof regarding Sam’s liability for fraud penalties under 26 U.S.C. § 6663.
. Debtors’ Pre-Trial Brief [ECF No. 1015] ¶ 121.
. Webb,
. See, e.g., Estate of Trompeter,
. DiLeo,
. See Garavaglia,
. Webb,
.More fully, the Supreme Court stated in Spies,
Congress did not define or limit the methods by which a willful attempt to defeat and evade might be accomplished and perhaps did not define lest its effort to do so result in some unexpected limitation. Nor would we by definition constrict the scope of the Congressional provision that it may be accomplished ‘in any manner.’ By way of illustration, and not by way of limitation, we would think affirmative willful attempt may be inferred from conduct such as keeping a double set of books, making false entries of alterations, or false invoices or documents, destruction of books or records, concealment of assets or covering up sources of income, handling of one’s affairs to avoid making the records usual in transactions of the kind, and any conduct, the likely effect of which would be to mislead or to conceal. If the tax-evasion motive plays any part in such conduct the offense may be made out even though the conduct may also serve other purposes such as concealment of other crime.
. Webb,
. Tr. Trans. 719:15-20(Sam).
. See pp, 431-41, supra.
. See pp. 423-31, 431-41, supra.
. See pp. 516-36, infra.
. See Joint Exs, 59, 61, 63, 65, 67, and 69, whereby Sam deferred annuity payments scheduled to commence on his 65th birthday to his 70th birthday, and 71, 73, 75, 77, and 79, whereby Sam deferred annuity payments scheduled to commence on his 68th birthday to his 73rd birthday,
. Tr. Trans. 2039:9-2052:23 (Sam describing on cross examination how, beginning as early as 2007 it became necessary to move money around the offshore system in order to meet annuity payment obligations); IRS Exs, 1131 at E0I-I0M-SW-0000017582 (letter dated May 31, 2013 from Tensas Limited (IOM) to Sam stating that Tensas Limited (IOM) “has not made full payments to you since 2010”); however, ¶ 175 of the Joint Stipulations shows that the last full payment from Tensas Limited (IOM) was received in 2008, 1135 at EOI-IOM-SW-0000013854 (letter dated May 31, 2013 from East Baton Rouge Limited (IOM) to Sam stating that East Baton Rouge Limited (IOM) “has not made full payments to you since 2011”); Amended Bankruptcy Schedule B, Exhibit B-16 [ECF No. 472] at p. 55 of 94 (indicating that, as of September 30, 2014, $70,544,877 in annuity payments from the offshore system were outstanding as to Sam with “no payment expected in the near term").
. See pp. 431-41, supra.
. See Amended Bankruptcy Schedule B, Exhibit B-16 [ECF No. 472] at p. 55 of 94. Although Sam scheduled these obligations as not paying in the near term, at trial he testified that he expects no further payments at all. Tr. Trans. 2941:l-8(Sam).
. See pp. 431-41, supra.
. See Joint Exs. 59, 61, 63, 65, 67, 69, 71, 73, 75, 77, and 79.
. See IRS Ex. 96 at WYLYSEC01112396 (memorandum drafted by Hennington to Sam, Charles, Evan, and Donnie: "As you are aware, we have been planning for some time for the commencement of the annuity payments. As we have studied the impact of these payments we have become increasingly concerned with the logistical problems of paying the annuities_ 1. When the payments are reported on your 1040, they will be on a separate line on page one for annuity payments. It is almost certain given the large amount of these payments that the reporting will result in an IRS audit. There is also a high likelihood that as a result of this audit the entire structure of the foreign system will be audited by the IRS.”).
. IRS Exs. 59, 61, 63, 65, 67, 69, 71, 73, 75, 77, and 79 (1998 private annuity amendments for Sam, all attesting that "WHEREAS, the intent of a deferred Private Annuity was to provide payment upon the retirement of Mr. Sam Wyly; and WHEREAS, Mr. Sam Wyly warrants that he does not anticipate retiring on the stated annuity commencement date ... Whereas, Mr. Sam Wyly desires the deferral of the private annuity until his anticipated retirement; and Whereas, the obligor ... agrees to defer the Private Annuity.”); IRS Exs. 59, 61, 63, 65, 67, and 69 (deferred annuities scheduled to begin paying on Sam’s 65th birthday until his 70th birthday) and IRS Exs. 71, 73, 75, 77, and 79 (deferred annuities scheduled to begin paying on Sam’s 68th birthday until his 73rd birthday); see also Tr. Trans. 1239:1-9 (Chatzky testifies that the annuities were deferred because "it was explained to me that originally Sam Wyly had intended to retire at the age of 68, and then I guess as time marched on, he enjoyed working, and he wanted to work for another five years; and, therefore, he — he had other sources of income than the annuity payment.”).
.See Wyly Exs. B ($15 million promissory note by Sam in favor of Security Capital effective January 30, 2002), E ($25 million promissory note by Sam in favor of Security Capital effective March 1, 2003), and F ($10 million promissory note by Sam in favor of Security Capital effective July 15, 2003).
. Joint Stipulations 43-47 (referring to the creation of Rosemary’s' Circle R Ranch Limited (IOM) in 1999; Cottonwood I Limited (IOM), Cottonwood II Limited (IOM), Spitting Lion Limited (IOM) in 2000; and Mi Casa Limited (IOM) in 2001); 306-320 (describing the Rosemary’s Circle R Ranch structure), 321-377 (describing the Cottonwood I Limited (IOM) and the Cottonwood II Limited (IOM) structures), 465-432 (describing the Spitting Lion Limited (IOM) structure). Recall that the Cayman LLCs that owned Rosemary’s Circle R Ranch Limited (IOM), Cottonwood I Limited (IOM), Cottonwood II Limited (IOM), Mi Casa Limited (IOM), and Spitting Lion Limited (IOM) were all funded with money that originated from the offshore system and was routed through Security Capital. Joint Stipulations ¶¶ 292, 303-305. See also pp. 423-31, supra; 516-36, infra.
. As French testified, the first large purchase of personal property occurred in mid-1996 with the purchase of Noon Day Rest by Sam’s wife, Cheryl. And, while expensive, that item pales in comparison to the expense associated with the real estate purchases. See SEC Tr. Trans. 1947:12-1949:7 (French referring to the purchase of Noon Day Rest: "Q, This was the first time the trusts in the Isle of Man, that you remember, were used to buy some kind of personal property, right? A. That is, I believe, correct.”); see also IRS Ex. 364 (documenting circumstances surrounding purchase of Noon Day Rest and its purchase price of £155,000.). See also pp. 423-31, supra; 516-36, infra.
. See Joint Exs. 81, 82, and 85, whereby Charles deferred annuity payments scheduled to commence on his 65th birthday to his 70th birthday, and 89, 91, 93, and 95, whereby Charles deferred annuity payments scheduled to commence on his 68th birthday to his 73rd birthday. Dee similarly extended annuity payments that were scheduled to commence on her 65th birthday to her 70th birthday. See Joint Ex. 87.
. The evidence shows that Dee relied entirely on Charles regarding all business, tax, and legal matters throughout their marriage. Tr. Trans. 159:20-160:15(Dee) (relied entirely on husband throughout marriage); 159:18-19(Dee) ("Q. Have you ever prepared a tax return? A. Oh, heavens no.”); 172:17-19(Dee) (never discussed tax matters with husband).
. Id. at 322:6-14 (Dee testifying that she does not know what a limited partner, general partner, limited partnership, or annuity is), 188:22-189:9 (Dee testifying she had never heard of Lincoln Creek IOM Trust), 192:8-11 (Dee testifying that she had never heard of Maroon Limited (IOM)).
. See id. at 1026:11-25 (Sam denies knowing that the offshore system was aggressive, but then admitting he recalls hearing "that word” from either French or another lawyer with respect to the offshore system, but qualifying it with "I don’t recall for what particular purpose they were speaking of its being seen as aggressive.”); 1034:7-9 (Sam testifying he did not know if Robertson also warned him the offshore system was aggressive) and 1034:10-1044:4 (Sam being impeached with IRS Ex. 85, a memo from Robertson containing her notes from a Tedder seminar stating the strategy was aggressive, to which Sam responds "[t]hat’s. what it says” and, when pressed for a yes or no answer, admitting ‘‘[i]f I had to choose between no and yes, I would go with yes.”), 1035:6-8 (Sam did not recall testifying that he would read anything Robertson copied him on) and 1037:7-17 (Sam’s prior deposition testimony that ”[y]eah, yeah, I read anything that Shari Robertson copied me on. I mean, I would see it.”); 1364:10-19 (Sam denying the offshore system was helped by secrecy, claiming "[i]t was an open book”) and 1367:15-19 (impeaching Sam with his testimony from the SEC Action — “Question: And that goal, making it harder for people to get to your money in the Isle of Man, was helped by secrecy. Right? Answer: Yes.”); 1382:20-24 (Sam testifying that he did not know that his lawyers, with his knowledge, tried to keep the IOM trusts’ ownership of securities under 5% to minimize SEC reporting requirements) and 1382:25-1392:10 (impeaching Sam with his testimony from the SEC Action); 2052:9-14 (Sam stating he does not remember personally writing off annuity payments) and 2647:23-2670:17 (impeaching Sam with letters he personally signed forgiving past due and future annuity payments). These are just a few of many examples of Sam being impeached while testifying before the Court.
. This is also true with respect to the badge of fraud of offering implausible or inconsistent explanations of behavior, to which we will apply the same timing analysis. See pp. 449-53, infra.
. Toussaint v. C.I.R.,
. Id.
. Id. at 312.
. Id. at 312-13.
. Id. at 309-13,
. Id. at 312 (internal citation omitted).
. Delvecchio v. C.I.R.,
. See pp. 413-23, supra.
. The outcome here might have been different if the IOM corporations owing the annuity obligations had simply been left alone to invest the money they realized from the exercise of the options and sale of the associated stock — even in investments Sam "wished” the IOM trustees to make, as he is a savvy and successful businessman after all — and then those IOM coiporations simply transferred the realized profits to other IOM entities to do with what the trustees decided (again, even consistent with Sam’s “wishes”). In other words, had the IOM coiporations owing the annuity obligations not been raided to support the families’ lifestyles, leaving them unable to satisfy their annuity obligations to Sam (and Charles until his death) as they came due, and income tax had been paid on all of that income when received, we might not be here today. And, even after the offshore entities were raided to support the families’ lifestyles, Sam could have "wished” for assets to be liquidated so that loans could be repaid and/or solvency could be restored and his annuities paid per the agreements with him. But, he didn't "wish” for that. And, as a result, it didn’t happen. Why? Because Sam (and Charles) got greedy and were prepared to "risk” litigation with the IRS once the offshore system was fully exposed because, as businessmen who had taken business risks all their lives, they expected to be able to settle with the IRS for "pennies on the dollar.” IRS Ex. 1199 ¶ 57 (p. 15) (Annex A, Admissions of Defendant Michael C. French) ("Sam Wyly said if the IRS challenged his use of the Offshore Trusts, he would litigate with the IRS for years and then settle for pennies on the dollars. French knew that Sam Wyly previously litigated against the IRS for years and then settled.”). Sam was questioned regarding his pennies-on-the-dollar statement during cross examination. He testified he did not recall the statement, and IRS' counsel sought to impeach him with French’s Consent. Tr. Trans. 1027:l-16(Sam). Sam’s counsel objected on hearsay grounds and, since the IRS did not have a persuasive response, that objection was sustained. Id. at 1027:17-1034:5. The Court notes, however, that a redacted copy of French’s Consent, which still includes the pennies-on-the-dollar statement, was subsequently admitted into evidence by agreement of the parties. Id. at 2900:9-13.
. Collateral Estoppel No. 56.
. SEC. Tr. Trans. 1004:1-3 (Boucher) (Q: Do you recall Sam Wyly joking, “Well, we’ll just fire the trustees if we [sic ] don't do what they [sic ] tell them? A: Yes.”). See, e.g., pp. 423-25, supra.
. Lisa, Laurie, and Kelly built homes on the Colorado property. Tr, Trans. 931:17-932:15 (Evan), 1514:24-1515:2 (Laurie) ("I live in a house here in Dallas on Crooked Lane that is owned by — by an Isle of Man trust, and I also have a second home I — that I go to in Colorado on the ranch). The record is unclear, however, whether Laurie’s sisters share a home or enjoy separate homes on the ranch,
. Recall that Laurie was required to put in 1% in order to be a co-owner, who then has the legal right, according to Meadows Owens, to use and enjoy the asset without paying for the fair rental value of the asset. Tr, Trans. 2542:1-2543:10 (Pulman),
. Wyly Ex. G (Financial Statements) at HST-PSI230623 (FloFlo balance sheet under category "Loans & Advances Receivable” showing Mi Casa Limited (IOM) with a book and fair market value of $3,215,000 each),
. The Court concludes that this badge of fraud is established for each of the years at issue in the Motions for the same reasons explained in connection with the Court’s analysis of the badge of fraud of offering false or incredible testimony. See pp. 446-49, supra.
. A Form 3520 is an information return filed with the IRS annually to report certain transactions with foreign trusts. Form 3520-A is the "Annual Information Return of Foreign Trust with a U.S. Owner.”
. See, e.g,, IRS Ex. 163 (Sam 2013 tax return) at 17 (Schedule B, Part III, Question 8). For tax years 1992 through 1995, the question was ‘‘[w]ere you the grantor of, or transferor to, a foreign trust that existed during [relevant year], whether or not you have any beneficial interest in it?” See, e.g., Joint Ex. 97 (Sam 1993 tax return) at SWY-LY020260 (Schedule B, Part III, Question 12). Since both questions ask whether the taxpayer is a grantor of a foreign trust that existed during the relevant year, the two versions of the question are not materially different for our current purpose.
. See, e.g., IRS Ex. 159 at 1.
. See, e.g., id. (Schedule C begins 53 pages into the exhibit, which is not Bates numbered).
. Tr. Trans. 2215:5-2217:19 (Hennington); Joint Ex. 108 (Sam 2004 tax return) at SWY-LY021663 (Question 16a) and SWYLY021723 (Form 1040 Pensions and Annuities).
. See Joint Exs. 110 (Sam 2006 tax return) at SWYLY022259 (Schedule C) and SWY-LY022351 (Schedule C, Statement 16), 111 (Sam 2007 tax return) at SWYLY022974 (Schedule C) and SWYLY023031 (Schedule C, Statement 19), 112 (Sam 2008 tax return) at SWYLY023109 (Schedule c) and SWY-LY023174 (Schedule C, Statement 23); IRS Exs. 74 (Sam 2004 tax return) at pp. 4 and 120, 75 (Sam 2005 tax return) at pp. 13 and 90, 159 (Sam 2009 tax return) at pp. 33, 53, 160 (Sam 2010 tax return) at pp. 9 and 60, 161 (Sam 2011 tax return) at 8 and 66, 162 (Sam 2012 tax return) at pp. 9 and 65, 163 (Sam 2013 tax return) at pp. 9 and 69. The referenced tax returns that are IRS exhibits are neither consecutively nor Bates numbered, so the Court’s pin cite is to the number of pages into the exhibit the referenced information may be found.
. Tr. Trans. 1592:20-1593:4 (Herrick).
. Id. Slightly over half of the income adjustments in the Computation Stipulations were due to the fact that this annuity income had, in fact, been reported. Id. at 1594:21-1595:11 (Herrick),
. ■ Id. at 2202:19-2217:19 (Hennington).
. Id.
. Id. at 2217:3-7 (Hennington).
. IRS' Amended Proposed Findings of Facts and Conclusions of Law [ECF No. 1103] at 202-203 (§ VIII, ¶¶ 112-119).
. Tr. Trans. 2202:19-2217:19 (Henning-ton).
. Id. at 2507:4-2508:2, 1914:4-1915:14 (Hennington).
. 26 U.S.C. §§ 1401, 1402. Net earnings from self-employment also include some partnership income. 26 U.S.C. § 1402(a).
. Dillon v. C.I.R.,
. IRS’ Amended Proposed Findings of Facts and Conclusions of Law [ECF No. 1103] at 202-03 (§ VIII, ¶ 114) (citing Newberry v. C.I.R.,
. Schelble,
. Tr. Trans. 3103:23-3106:7 (Dubinsky).
. Form 5471 is another information return to be filed by U.S. taxpayers with respect to certain foreign corporations.
. See Computation Stipulations ¶¶ 7.A-12.B, 20.A-25.B.
. As will be explained in the International Penalties section of this opinion, the Wylys successfully structured certain offshore transactions in a way that did not require the filing of these forms. See pp. 550-76, infra.
. Spies,
. See pp. 550-76, infra; IRS Ex. 567 at SWYLY007639 (email dated December 9, 2002 from Hennington to Alan Stroud, a lawyer at Meadows Owens, stating: "I am sure I read this at the time and overlooked or did not pay attention to the 3520 filing requirement. It seems that we would have preferred to not have anything reportable on the note if that was a possibility.”); IRS Ex. 570 (email dated January 9, 2003 between Hennington and Boucher where Hennington expresses concern that certain loans may be subject to reporting requirements); SEC Tr. Trans. 1720:14-1721:6 (French) (Tedder told Sam that making SEC filings could jeopardize the tax status of the offshore system). In addition, a revenue agent involved in Sam’s and Charles' audit testified that he had still not received certain audited financials that the Isle of Man corporations were under an obligation to prepare, and that this did "seem a little disconcerting.” Tr. Trans. 1625:23— 1627:1 (Herrick). The revenue agent also admitted “we’re at about 94 percent that we have now” and that "given the dollar amount in question here, it's not going to make a material difference in the number ... we're at trial now. We aren’t going to change the number anymore.” Id.
. See Joint Exs. 142-175, which are all of the Forms 3520 and Forms 3520-A in the record. For example, Forms 3520 and 3520-A were filed for the grantor trusts that Sam settled through which the 1996 annuity transactions were undertaken — ie., Sitting Bull IOM Trust, Crazy Horse IOM Trust, Arlington IOM Trust, and Tallulah IOM Trust. Joint Exs. 145-162. The only Form 3520 filed for the Bulldog IOM Trust was signed and dated by Sam as the settlor on June 6, 1992, was filed on a whitepaper schedule despite the existence of an IRS form that could have been used, and shows that $100 was transferred into the trust. Joint Ex. 142. Likewise, the only Form 3520 filed for the Lake Providence IOM Trust was signed and dated by Sam as the settlor on January 25, 1993, was filed on a whitepaper schedule despite the existence of an IRS form that could have been used, and shows that $100 was transferred into the trust. Joint Ex. 144. The singular Form 3520 for Delhi IOM Trust was signed by Sam on the same date and was also a whitepaper schedule that showed $100 being transferred into the trust. Joint Ex. 145. No Forms 3520 or 3520-A were filed for Bessie IOM Trust or La Fourche IOM Trust.
. See Joint Exs. 150, 153-157, and 160-162.
. See Joint Exs. 146 and 147.
. See Joint Exs. 148, 149, 151, and 152.
. See, e.g., Joint Ex. 150.
. See 26 U.S.C. § 6048, Joint Exs. 146 (Form 3520 filed and signed by Sam as grant- or of Tallulah IOM Trust showing transfer of $61,770,607 involving Tallulah IOM Trust. This form is not dated, and although the transfer is listed as occurring on September 8, 1992 the form itself indicates in its upper left-hand corner that it was revised in June of 1995. According to Statement 3 attached to this form, the transfer consisted of an investment in a limited partnership interest in “Tal-lulah Limited.”), 147 (Form 3520 filed and signed by Sam as grantor of Tallulah IOM Trust showing transfer of $5,265,566 involving Tallulah IOM Trust. This form is not dated, and although the form lists the transfer as occurring on April 30, 1993, the form itself indicates in its upper left-hand comer that it was revised in June of 1995. According to Statement 3 attached to this form, the transfer consisted of an investment in a limited partnership interest in "Tallulah Limited”).
. Joint Exs. 146 and 147.
. See Joint Stipulations ¶¶ 223-256; Joint Exs. 142-175. The fact that these forms had to have been filed years late is of no economic consequence here, however, as the IRS is not
. Joint Ex. 142.
. Joint Ex. 163.
. See pp. 556-57, infra.
. This finding applies to years 1992 through 2013, even though the IRS does not seek International Penalties for years 1992 through 1995. The IRS does not seek penalties for 1992 through 1995 presumably because during these years, the penalties under § 6677 and § 6038 were relatively de minimis and increased in 1996 and 1997 respectively. See Small Business Job Protection Act of 1996, Pub.L. No. 104-188, § 6677, 110 Stat. 1755 (increasing penalties under § 6677); Taxpayer Relief Act of 1997, Pub.L. No. 105- . 34, § 6038, 111 Stat. 788 (increasing penalties under § 6038). Nevertheless, § 6038 still required that Sam and Charles file Forms 5471 in years 1992 through 1995. See, e.g., 26 U.S.C. § 6038(a), (e)(1) (1994). This is because the relevant definitions of control under § 6038(e)(1) and "the rules prescribed by section 318(a) for determining ownership of stock” to which subsection (e)(1) refers — and by which the Court concludes that Sam and Charles were required to file Forms 5471— have not been amended from 1992 to date. See 26 U.S.C. §§ 318(a),- 6038(e)(1). Since Sam and Charles did not file any Forms 5471 from 1992 through 1995, the badge of fraud of filing false or misleading documents still exists for these years due to the absence of Forms 5471 during those years. This badge of fraud also exists during 1994 and 1995 as to Sam and Charles for an additional reason. Section 6048(a)(1) required a Form 3520 to be filed upon "the creation of any foreign trust by a United States person.” 26 U.S.C. § 6048(a)(1) (1994). Thus, when the Bessie IOM Trust and the Tyler IOM Trust were created in 1994 and the La Fourche IOM Trust and Red Mountain IOM Trust were created in 1995, Sam and Charles should have filed Forms 3520 documenting these events. See Joint Stipulations 28, 48, 81, 88. This means that the badge of fraud of filing false or misleading documents exists in 1994 and 1995 by virtue of the fact that these Forms 3520 were not filed.
. Charles and Dee checked the box “yes” on their 1992 joint tax return. IRS Ex. 27A at SECI00028718 (Question 12).
. See Joint Exs. 97 (Sam 1993), 103 (Sam 1999), 104 (Sam 2000), 110 (Sam 2006), 111 (Sam 2007), 112 (Sam 2008), 120 (Dee and Charles 1993), 127 (Dee and Charles 2000), 128 (Dee and Charles 2001), 129 (Dee and Charles 2002), 130 (Dee and Charles 2003), 133 (Dee and Charles 2006), 134 (Dee and Charles 2007), 135 (Dee and Charles 2008), IRS Exs. 29A (Dee and Charles 1994), 30 (Dee and Charles 1995), 31 (Dee and Charles 1996), 32 (Dee and Charles 1997), 33 (Dee and Charles 1998), 34 (Dee and Charles 1999), 40 (Dee and Charles 2004), 42 (Dee and Charles 2005), 50 (Dee and Charles 2009), 52 (Dee and Charles 2010), 54 (Dee and Charles 2011), 55 (Dee 2012), 56 (Dee 2013), 71 (Sam 2002), 135 (Sam 1992), 140 (Sam 1994), 141 (Sam 1995), 142 (Sam 1996), 151 (Sam 1997), 152 (Sam 1998), 154 (Sam 2001), 74 (Sam 2004), 75 (Sam 2005), 155 (Sam 2003), 159 (Sam 2009), 160 (Sam 2010), 161 (Sam 2011), 162 (Sam 2012), 163 .(Sam 2013). Charles and Dee checked “Yes” in response to this question on their 1992 tax return. IRS Ex. 27A (Dee 1992). There is no explanation in the record as to why they checked the box “Yes” in 1992, but "No” thereafter.
.See Joint Exs. 110 (Sam 2006), 111 (Sam 2007), 112 (Sam 2008); IRS Exs. 71 (Sam 2002), 74 (Sam 2004), 75 (Sam 2005), 155
. See Joint Exs. 130 (Dee and Charles 2003), 133 (Dee and Charles 2006), 134 (Dee and Charles 2007), 135 (Dee and Charles 200.8), 141 (Dee 2013); IRS Exs. 40 (Dee and Charles 2004), 42 (Dee and Charles 2005), 50 (Dee and Charles 2009), 52 (Dee and Charles 2010), 54 (Dee and Charles 2011).
. See, e.g., IRS Ex. 155 (Sam 2003 tax return) at 47-50.
. See Joint Ex. 38 (Dee and Charles 2003) at SWYLY029539, 71 (Sam 2002) at 78-81, 155 (Sam 2003) at 47-146.
. See, e.g., IRS Exs. 40 (Dee and Charles 2004) at 65, 74 (Sam 2004) at 86.
. See IRS Exs. 71 at 80 (Sam 2002, esti-: mating $13 million), 155 at 49 (Sam 2003, estimating $6 million); Joint Ex. 130 at SWY-LY029541 (Dee and Charles 2003, estimating $7 million), Note that, according to the Computation Stipulations, Sam owes a little over $16 million in income tax for 2002 and a little over $5 million in income tax in 2003. Dee and Charles owe a little over $3.25 million for 2003. See Computation Stipulations at Attachments A and B.
. See, e.g., IRS Exs. 42 (Dee and Charles 2005)at 62-69, 75 at 69-105 (Sam 2005).
. See Joint Exs. Ill at SWYLY023014-23015 (Sam 2007), 134 at SWYLY030969 (Dee and Charles 2007).
. IRS Ex. 163 atpp. 43, 45, 47 (Sam 2013).
.
. Id. at 2070.
. Id. at 2070-71.
. See Fiore v. C.I.R.,
. Fiore,
.Fields,
. Fiore,
. U.S. v. Faulkner,
. U.S. v. Jones,
. Id. at 979 n. 3.
. Tr. Trans. 2114:9-16 (Hennington).
. There is no innocent spouse relief for gift tax liability. The innocent-spouse provisions apply only to income taxes imposed by subti-tie A of the Internal Revenue Code, plus any related interest or penalties. See 26 C.F.R. § 1.6015 — 1(a)(3).
. 26 U.S.C. § 6015(b)(1)(A) — (E).
. The IRS asserts that innocent spouse relief is only available through 2009 because Charles did not sign the 2010 through 2013 tax returns. However, the Court disagrees with the IRS and concludes that the returns for 2010 and 2011 are joint returns notwithstanding the lack of Charles’ signature and that Charles died in 2011. See 26 U.S.C. § 6013(a)(2) (“no joint return shall be made if the husband and wife have different taxable years; except that if such taxable years begin on the same day and end on different days because of the death of either or both, then the joint return may be made with respect to the taxable year of each.”). Dee’s 2010 and 2011 tax returns were filed as joint returns. IRS Exs. 52 (Dee and Charles’ original 2010 joint return), 53 (Dee and Charles’ amended 2010 joint return), 54 (Dee and Charles’ 2011 joint return), 55 (Dee’s 2012 single return), 56 (Dee’s 2013 single return).
. See pp. 474-76, infra.
. See pp. 388-89, supra.
. 26 U.S.C. § 6015(b)(1)(B).
. Id. §§ 6015(b)(3), 6662(d)(2)(A).
. 26 C.F.R. § 1.6015-l(h)(4).
. Id.
. Id.
. Id.
. Id.
. Id.
. This agreement is contingent upon (i) the SDNY Court’s determination of foreign grant- or trust status being affirmed on appeal, which appeal is currently pending before the Second Circuit Court of Appeals, and/or (ii) this Court’s collateral estoppel decision being affirmed on appeal, assuming such an appeal is taken.
. Indeed, Dee credibly testified that every penny of the income that was earned during her marriage was earned by her husband Charles. Tr. Trans. 164:2-4(Dee).
. 26 C.F.R. § 1.6015-2(c).
. Id.
.
. Id. at 333-34 & n. 16.
.Id. at 330.
. Id. at 331 (the amounts in dispute "roughly correspond to the improperly deducted amounts that the Cheshires used to pay off their mortgage”).
. Id, at 334-35. ("Appellant's defense consists only of her mistaken belief that money spent to pay off a mortgage is properly deductible from retirement distributions. Ignorance of the law cannot establish an innocent spouse defense to tax liability.”).
.
. Id. at *1-2.
. Id. at *6.
. Id.
.
. Id. at 1344-46.
. Id. at 1346.
. Id.
. Cheshire,
.
. Id.
. 26 C.F.R. § 1.6015-2(c).
. See pp. 389-464, supra.
. 26 U.S.C. § 6015(b)(1)(D).
. 26 C.F.R. § l,6015-2(d),
. Cheshire,
. Cheshire,
. Id.
. Id.
.
.
.Id. at *6-7.
. Id. at *7.
. Id.
. Hall v. C.I.R.,
. See Varela v. C.I.R.,
. Haltom,
. Becherer v. C.I.R.,
. See pp. 389-462, supra.
.See pp. 461-64, supra.
. See pp. 389-462, supra.
. See Haltom,
. 26 C.F.R. § 1.6015-2(d).
. Id.
. Those tax courts who analyze the desertion factor tend to group it with the factor of whether the spouses are divorced or separated. See Hall,
. Haggerty v. C.I.R.,
. Von Kalinowski v. C.I.R.,
. Rev. Proc.2013-34, 2013-
. Haggerty,
. Rev. Proc.2013-34, 2013-
. See Agudelo v. C.I.R.,
. See Hopkins v. C.I.R.,
. Id.
. Rev. Proc.2000-15, 2000-
. Rev. Proc.2013-34, 2013-
. Hall,
. Haggerty,
. Rev. Proc.2013-34, 2013-
. See Cutler,
. See pp. 465-68, supra.
. Tr. Trans. 159:20-160:15(Dee) (relied entirely on husband throughout marriage).
. Id. at 164:5-165:3(Dee) (first heard the name Soulieana at her deposition in July 2015, never discussed IOM structure with anyone before bankruptcy case filed), 165:22-166:23; 174:16-24(Dee) (didn’t ever see Eise-man or Marguerite Green invoices at the time purchases were made), 182:10-183:3; 183:18-20(Dee) (never heard of Tyler IOM Trust or Keith King), 184:20-185:11, 186:12-15(Dee) (never heard of Red Mountain IOM Trust or Shaun Cairns), 322:6-14(Dee) (does not know what a limited partner, general partner, limited partnership, or annuity is), 188:22-189:9(Dee) (never heard of Lincoln Creek IOM Trust), 192:8-11 (Dee) (never heard of Maroon Limited (IOM)).
. Rev. Proc.2013-34, 2013-
. Haggerty,
. See pp. 468-70, supra.
. See Wang v. C.I.R.,
. See IRS Ex. 55 (Dee 2012) at 8, 56 (Dee 2013) at 4. The Court concludes elsewhere in the Memorandum Opinion that Dee is in fact a grantor of the various Isle of Man trusts that make up Charles’ offshore system. See pp. 553-57, infra.
. Haggerty,
. 26 U.S.C. § 6015(b)(1)(D).
. Tr. Trans. 160:10-161:14(Dee).
. 26 C.F.R. § 1.6015-5(b)(l).
. Id. § 1.6015 — 5(b)(2)(i). One of the examples laid out under §T.6015-5(b)(4) specifically discusses a proof of claim: "Example 5. W files a Chapter 7 bankruptcy petition on July 10, 2000. On September 5, 2000, the United States files a proof of claim for her joint 1998 income tax liability. W elects relief with respect to the 1998 liability on August 20, 2002. The election is timely because it is made within two years of the date the United States filed the proof of claim in W’s bankruptcy case.” 26 C.F.R. § 1.6015— 5(b)(4).
. 26 U.S.C. § 6664.
. For example, Sam relies on the definition of "advice” in § 1.6664-4(c)(2) in support of his argument that he need not have read the opinions or memoranda that contained the advice he received. See Debtors’ Post-Trial Brief [ECF No. 1117] at 49. The Debtors cite to § 1.6664-4 at other points as well, See Debtors’ Amended Proposed Findings of Fact and Conclusions of Law [ECF No. 1102] at 180 n.723; Debtors’ Post-Trial Brief [ECF No. 1117] at 31 n.41, 40 n.64, 47 n.82, 50; Debtors’ Post-Trial Reply [ECF No. 1121] at 24-25, 36 n.92, 41, 43, 45.
. See, e.g., IRS’ Amended Proposed Findings of Facts and Conclusions of Law [ECF No. 1103] 243, 245, 246; IRS Pre-Trial Brief [ECF No. 1018] at 120-21. IRS Post-Trial Brief [ECF No. 1118] at 6-9, 13, 17, 19; IRS Post-Trial Reply [ECF No. 1120] at 19, 22, 23.
. The Court acknowledges that 26 C.F,R. § l,6664-4(c) was not in effect for all of the years at issue, and again stresses that it is using this regulation only as a guide when engaging in an analysis of all of the facts and circumstances surrounding Sam’s reasonable cause and good faith defense/attempted negation of fraudulent intent. Section 1,6664-4(c)'s explanation of reliance on the advice of a professional was first added to the regulation in 1995, see T.D. 8617, 1995-
. 26 CiF.R. § 1.6664-4(a); see, e.g., Sanchez,
. Brinkley v. C.I.R.,
. Thomas v. C.I.R.,
. See, e.g., Sanchez,
. See, e.g., Grossman v. C.I.R.,
.See Richardson,
. See Richardson,
. See, e.g., Debtors' Amended. Proposed Findings of Facts and Conclusions of Law [ECF No. 1102] at 154-55 ("The Wylys never intentionally failed to pay any tax they believed they owed. At all times, the Wylys acted on the advice of competent tax advisors, and they paid all taxes they believed were due. The IRS has no evidence that the Wylys believed that the conclusions of their advisors on these complex and uncertain issues were wrong. Thus the IRS cannot carry its burden as to fraud.”).
. See p. 389, supra.
. Davis,
. See, e.g., Durrett v. C.I.R.,
.In so finding, the Court acknowledges that at least some tax courts have held that
. 26 C.F.R. § l,6664-4(c).
. Sam received some advice that is not relevant to the issues we will discuss here in detail. For example, Sam received twelve written opinions from Chamberlain, Hrdlicka, White, Williams, & Martin dated October 15, 2003, each one addressing whether each of the twelve annuity transactions that Sam undertook in 1992 and 1996 were listed transactions mandating disclosure under 26 C.F.R. § 1.6011-4(a). The firm concluded that they were not. See Wyly Exs, DM-DX. Similarly, Sam received twelve substantively identical opinion letters from De Castro, West, Chodo-row, Glickfeld, & Ness, Inc. dated October 15, 2003 addressing whether each of the twelve private annuity transactions was a “reportable transaction” under 26 U.S.C. § 6011; while worded differently, the same question addressed by the Chamberlain Hrdlicka firm. The De Castro West firm reached the same conclusion that the Chamberlain, Hrdlicka firm reached — the annuity transactions were not subject to disclosure as a reportable transaction. See Wyly Exs. DM-DX. The fact that the private annuity transactions were not a listed transaction is not in dispute among the parties here; thus, these opinions are not relevant to any issue in dispute.
.In their pre-trial briefing, the Debtors argue that they have established reasonable cause for two reasons: (i) because they relied on the advice of their counsel, and (ii) because there was an honest difference of opinion as to the proper application of the tax law at issue here. The Court analyzes the Debtors' honest difference of opinion argument in
. Wyly Ex. BO. Dee and Charles received identical opinion letters from Pratter, Tedder & Graves, See Wyly Exs. BP (Charles), BQ (Dee).
. Wyly'Ex. BO at 6221.
. Id. at 6222.
. Id. at 6222-6224.
. Id. at 6225 (opinion A).
. Id. at 6226 (opinion B).
. Id. at 6239 (opinion H).
. Id. at 6240 (opinion I), although this transfer never occurred.
. Id. at 6242.
. As did the four Nevada corporations that acquired the options and warrants from Charles. See Wyly Exs. BS, BU, BV, and BZ.
. See Wyly Exs. BR, BT, BW, BX, BY, and CA.
. Wyly Ex. BR at WYLYSEC01103165.
. Id. at WYLYSECO1103167.
. Chatzky testified that he worked with Tedder's firm from time to time on particular clients, but that at some point in time they became partners in the same firm, While Chatzky could not be precise as to the timing, they became partners sometime between the April 1992 opinion letters just discussed and the May 19, 1993 opinion letters. Tr, Trans. 1134:12-1136:24 (Chatzky). Moreover, by February 22, 1996, Tedder and Chatzky were no longer law partners because Tedder “had a penchant for making statements to people that were either questionable or flatly un-true_” Id. at 1137:15-17. According to Chatzky, this made him uncomfortable, so the firm dissolved and Chatzky returned to practicing law through his own firm, Chatzky & Associates. Id. at 1138:18-1139:9. After the dissolution of their law firm, Chatzky testified that he no longer worked on common clients ■ with Tedder, id. at 1139:16-20, and has never seen him again, id. at 11411-5,
. • See Wyly Exs. CB (Lake Providence IOM Trust) at SWYLY005378 and CC (Delhi IOM Trust) at SWYLYSEC01100186. The letters are identical and, based on the factual assumptions contained in the letters, the firm opines that "it is more likely than not that the trust will be construed to constitute a valid non-grantor trust for United States taxation purposes provided that the trust operates in accordance with the terms and provisions contained in the Trust Agreement.”
. Tr, Trans. 1170:9-11 (Chatzky).
. In fact, while Debtors' counsel attempted to refresh Chatzky’s recollection using a draft opinion letter dated February 2, 1992, that draft is unsigned and was not offered into evidence. Accordingly, there is no evidence in the record as to whether an opinion regarding the Bulldog IOM Trust was ever finalized, signed and issued to Sam. It goes without saying, therefore, that we have no idea on this record what such an opinion, if ever finalized, signed and issued, would have said.
. Neonatology Assocs.,
. See Neonatology Assocs.,
. Id. at 99.
. 6611, Ltd. v. C.I.R.,
. 106, Ltd.,
. Id. at 79 (quoting Tigers Eye Trading, LLC v. C.I.R.,
. Id.; see also Blum v. C.I.R.,
. Paschall v. C.I.R.,
. 106 Ltd.,
. Stobie Creek Inv. LLC,
. Chamberlain,
. Collateral Estoppel No-. 5 ("In early to mid-1991, Sam Wyly asked Robertson to attend a seminar held by lawyer and trust promoter David Tedder on the use of foreign trusts as a method of asset protection and tax deferral) (emphasis added).
. See IRS Exs. 96 (memo from Hennington and Boucher to, among others, Sam and Charles) at WYLYSEC01112395 § V.c, Ex. 97 (memo from Boucher and Hennington to, among others, Charles and Sam) at 2 ("They [the IRS] are not comfortable from a reasonable cause basis for penalties if the taxpayer relied solely on the legal opinion written by the same person who was promoting the structure (Teddar [sic].’’).
. Tr. Trans. 1052:1-4 (Sam admitting to having referred to Tedder as “a pitchman, a salesman, and a rainmaker” and that Tedder and Chatzky were the “architects” of the offshore system). See also SEC Tr. Trans. 1717:4-15 (French testifying that Tedder "had something to sell and he was a little bit of a salesman”), 3773:5-11 (French testifying he thought of Tedder as “a little bit of like a hustler”); Wyly Ex. OB at WYLY-SEC01112416-2417 (Lubar referring to Ted-der as a promotor).
. Tr. Trans, at 1137:15-17 (Chatzky).
. Id at 1137:18-1138:21 (Chatzky).
. Id at 1138:18-1139:9 (Chatzky).
. Mat 1190:17-23 (Chatzky).
. Sam confirms that Tedder “pitched” his offshore system to Sam and Charles at a meeting at Sam's home in Malibu in 1992. Tr. Trans. 1050:23:21-25(Sam). Sam was then asked — "You’ve described Mr. Tedder as a pitchman, a salesman, and a rainmaker. Is that correct,” to which Sam replied “yes.” Id at 1052:1-4. Sam was then asked "and he was the architect of this offshore system, wasn't he?” Sam’s responds "[h]e and his firm, including Mr. Chatzky, were the architects of it.” Id at 152:5-8.
. Tr. Trans. 1162:8-17 (Chatzky).
.Id. 702:4-11 (Sam explaining that after Tedder’s New Orleans seminar, "the next thing after that was I had a session with the— the two principals in the law firm in California who were out there. Michael Chatzky was sort of the legal scholar who wrote the documents to set it up, and David Tedder was sort of the []rain maker, the marketer of the — for the legal services.’’); 1051:23-25 (Sam stating "I think I described him [Ted-der] as the rainmaker and the more scholarly attorney as Mr. Chatzky — of the partners of the firm, is my take on it.”), 1074:3(Sam) ("Q. And Pratter, Tedder & Graves as Mr. Tedder’s law firm. Is that correct? A. Yes, Mr. Ted-der, Mr. Chatzky and others.”).
. See id. at 1190:18-23 (Chatzky) ("It’s my understanding that the party, the client — Sam Wyly or Charles Wyly, whoever the appropriate client was at the time — engaged Pratter, Tedder, & Graves to — to draft the opinion and, therefore, the opinions were submitted to David Tedder for his signature.”). In 1992, when Chatzky ghost wrote the opinion letters for Tedder, he and Tedder were not partners. Id. at 1135:21-11136:3 (Chatzky).
. See pp. 371, 414-15, supra; Collateral Estoppel No. 18.
. See pp. 413-16, supra.
. As will be explained later, acting on Sam’s behalf, Hennington received advice from Meadows Owens in October 2003 that Sam had a "reportable position” contrary to Lubar’s conclusions — both those expressed originally in 1993 and those expressed in mid-2003, after Lubar did further research at Hennington's request, again acting on Sam’s behalf. See pp. 491-93, infra.
. See, e.g., Wyly Ex. KL (Confidential Conference Outline dated July 14, 1999), IRS Ex. 110 (Confidential Conference Outline dated April 25, 2000), & IRS Ex. Ill (Confidential Conference Outline dated September 7, 2000).
. Owens died in July 2003. Thus, he did not testify at trial and the IRS objected to the admission of any testimony from Sam or Evan concerning what Owens had told them on hearsay grounds. That lead to the Debtors’ arguments that the purported advice was not being offered for its truth, but rather the impact the receipt of that purported advice had on Sam’s state of mind.
.As the Court stated in ruling on the IRS’ objection to the admission of Evan's testimony regarding advice given by Owens to Sam, "[gjiven that it is being stipulated that the evidence is coming in not for the truth of the matter asserted but the impact that the statements, whatever they are, whether accurate or not, had on the state of mind of Sam Wyly and then, I guess as corroboration, Evan Wyly since he was also at the meeting, the Court will admit it for that limited purpose.” Tr. Trans. 1674:9-20 (oral ruling).
. Tr. Trans. 1084:16-1089:13 (Evan); Laurie recalled the family meetings covering more personal matters than financial matters, id. 1512:6-8, and she could not recall anything specific Owens discussed at such meetings, id. 1510:4-12. Hennington recalled Owens attending a family meeting that she attended, and that Owens discussed the IOM trusts and corporations "in a broad sense, Rodney gave an overview to the family.” Id. 1922:2-14 (Hennington),
. IRS Ex. Ill at SWYLY009417 (emphasis in original).
. Of course, the IRS objected on hearsay grounds to Evan attempting to testify as to what Owens actually said at the family meetings. And, the Court was prepared to sustain the objection, which led to the Debtors’ argument that the testimony was being offered, not for the truth of the matter asserted but for its impact on Sam’s state of mind. As the Court stated in ruling on the IRS’ objection to the admission of Evan’s testimony, “[gjiven that it is being stipulated that the evidence is coming in not for the truth of the matter asserted but the impact that the statements, whatever they are, whether accurate or not, had on the state of mind of Sam Wyly and then, I guess as corroboration, Evan Wyly since he was also at the meeting, the Court will admit it for that limited purpose.” Tr. Trans. 1674:9-20 (oral ruling).
.See, e.g., IRS Exs. KJ (a memorandum to French and Robertson regarding loans from foreign grantor and non-grantor trusts (without analyzing the Wyly trusts per se)) and KM (a memorandum to Owens and Pulman from Stroud (at Meadows Owens) discussing the disadvantages of direct foreign investments in U.S. real property).
. Tr. Trans. 604:25-605:4 (Evan).
. Id. at 752:5-754:7 (Evan).
. IRS Ex. 96.
. IRS Ex. 99 at WYLYSEC01109030.
. IRS Ex. 96 at WYLYSEC01112399-2401.
. Tr, Trans. 2561:7-11 (Pulman testifying that Hennington met with Cousins around September 19, 2003, while Pulman was out of the office); 2563:19-2564:2 (Meadows Owens was asked for advice regarding Sam’s tax return that was due October 15, 2003); 2567:17-18 (“we didn't have a lot of time, Between late September and October 15th,”),
. Wyly Ex. OC. Tr. Trans. 1974:20-1983:1 (Hennington discussing Wyly Ex. OC),
. Wyly Ex. LQ. See also Wyly Ex. OC (Cousins’ notes from an October 8, 2003 meeting among various Meadows Owens attorneys and Hennington in which Meadows Owens explained five options to address Sam’s upcoming tax filing deadline in light of Lubar’s memorandum and anonymous meeting with the IRS); Tr. Trans. 2564:6-8, 2605:20-2606:13 (Pulman discussing Wyly Ex. LQ).
. Wyly Ex. LR; Tr. Trans. 2566:9-2571:24, 2618:16-2621:17 (Pulman discussing Wyly Ex. LR).
, According to Pulman, a “reportable position” “means basically that the position in the tax law is arguable ... it’s an arguable posi
. Tr. Trans. 1981:19-1982:2 (Hennington discussing October 8, 2003 meeting with various Meadows Owens lawyers where the attorneys recommended that the Wylys file Form 8275 disclosures because ”it allowed us to fully report the [Lubar] issue and protect against penalties, but at the same time we had a reportable position to continue to prepare the tax returns in the manner that we always had."); Wyly Exs. LQ (internal Meadows Owens memorandum dated October 1, 2003, analyzing 26 U.S.C. § 674 and concluding there could be two reasonable interpretations of the statute) and LR (internal Meadows Owens Memorandum dated October 19, 2003, analyzing 26 U.S.C. §§ 674 and 679 and concluding there was an arguable position that the 1992 trusts were non-grantor trusts); Tr. Trans. 2564:6-8, 2605:20-2606:13, 2566:9-2571:24, 2618:16-2621:17 (Pulman discussing Wyly Exs. LQ and LR).
. Tr. Trans. 2587:25-2588:13 (Pulman) ("Q: You never came to a final conclusion whether the '92 trusts were non-grantor trusts. Correct? A: I didn’t issue — I didn't come to an opinion whether they were foreign non-grantor. I came to a view as to whether [there] was a reportable position. Q. Right. Just for purposes of the tax return? A. Yes.”).
.Id. at 1787:9-1788:8 (Cousins testifying regarding Wyly Ex. OD, a discussion points memorandum used for an October 15, 2003 meeting between Cousins, Sam, and Evan, and stating "[w]e could not tell whether or not Mr. Lubar’s concerns were correct.”). See also 2529:16-19 (when Pulman began working on Wyly matters in 1999, Owens told him “there was an offshore trust and that it was a foreign grantor trust that had been grandfathered by the '95 legislation”); IRS Ex. 112 (Confidential Conference Outline dated September 7, 2000, which Owens used to explain the trust structure to Hennington when she was first appointed CFO of Highland Stargate) at 2 (stating the 1992 trusts are nongrantor foreign trusts) and 6 (stating the 1994 and 1995 trusts are foreign grantor trusts); Wyly Ex. LI at SWYLY09114-9117 (memorandum dated January 29, 2001 from Owens to the Wylys c/o Hennington and Boucher stating “[a]ll of the foreign trusts are currently exempted from U.S. income tax regimes based upon the non-foreign grantor trust (NFGT) and/or foreign grantor trust (FGT) characterization under the [IRC]”). However, there is no persuasive evidence in the record that Owens or any other attorney with Meadows Owens did anything other than accept the classifications stated in the Tedder opinion letters or trust documents themselves as correct.
.Tr. Trans. 2587:24-2588:13 (Pulman testifying that he never came to an opinion regarding whether the 1992 trusts were non-grantor trusts; he only "came to a view as to whether [there] was a reportable position.”); 2620:6-18 (Pulman explaining that a "reportable position” "means basically that the position in the tax law is arguable ... it’s an arguable position that can go either way.”); 2621:4-17 (Pulman testifying that Kniffen (another Meadows Owens attorney) "came to a view that there was an arguable position that [the 1992 trusts] were non-grantor trusts— foreign non-grantor trusts.”).
. See pp. 415-23, supra.
. See IRS Ex. 806.
. Id. at WYLYSEC00010967.
. Id. at WYLYSEC00010967-968.
. Id. at WYLYSEC000100968-969 (emphasis added).
. Tr. Trans. 583:23-584:7 (Evan); see also SEC Tr. Trans. 3753:5-14 (French testifying that he believed that King had made substantial money previously dealing with the Wylys in South African bonds, which is why he was recruited by French); Collateral Estoppel No. 23 ("These transactions were shams intended to circumvent the grantor trust rules. French and Buchanan, acting as the Wylys’ agents, recruited King and Cairns to create a falsified record of a gratuitous foreign grantor trust.”).
. Cairns Depo Tr. 46:18-47:4, 158:6-7.
. Tr. Trans. 583:23-584:7 (Evan); see also SEC Tr. Trans. 3753:2-14 (French).
. Collateral Estoppel No. 22 ("Shortly after these trusts were settled, Cairns’s trust management company was hired to serve as trustee for some of the Wylys' IOM trusts.”) Joint Stipulations ¶¶ 66 and 102, (showing that Cairn’s company, Wychwood Trust Limited, served as trustee for Delhi IOM Trust, La Fourche IOM Trust, and Red Mountain IOM Trust).
. Collateral Estoppel No. 24; Cairns Depo. Tr. 46:5-13; 56:9-12 (discussing his failure to fund the trusts with the stated $25,000); SEC Tr. Trans. 3755:10-3757:22 (French testifying regarding King’s failure to fund); IRS Exs.
. IRS Exs. 214 (November 16, 1995 fax from French to Buchanan regarding funding issues), 178 at 02517 (November 26, 1995 faxes from Buchanan to French regarding funding issues).
. 26 C.F.R. § 1.6664-4(c)(ii).
. Id. § 1.6664 — 4(c)(iii)(2).
. Id. § 1.6664-4(c)(ii). Obviously, French is that other person. Just as advice can be received directly or indirectly under the Tegu-lation, factual assumptions can be given directly by the taxpayer or indirectly by another person acting on the taxpayer’s behalf.
. Chatzky and Tedder are no longer working together or law partners, Tr. Trans. 1136:15-1137:2 (Chatzky testifying that he had ended his partnership with Tedder by February 22, 1996). Chatzky’s firm has been retained by this time to represent the Wylys. IRS Ex. 108 (fax from French to Chatzky dated February 1, 1996 discussing Chatzky's fee structure).
. See Wyly Ex. CL Chatzky and Associates also issued four substantively identical opinion letters dated November 27, 1996 to Crazy Horse IOM Trust, Arlington IOM Trust, Sitting Bull IOM Trust, and Tallulah IOM Trust. See Wyly Exs. CL, CN, CO, and CR. These written opinions do not change the Court’s analysis of Sam’s reasonable cause and good faith defense as it relates to the 1996 annuity transactions.
. Wyly Ex. Cl at SWYLY010365.
. Id. at SWYLY010366.
. Id. at SWYLY010367.
. Id.
. Id. (emphasis added).
. Id. (emphasis added).
. Id. at SWYLY010369.
. Id. at SWYLY010371.
. Id. at SWYLY010373.
. Id. at SWYLY010376.
. Id. at SWYLY010379.
. Id. at SWYLY010381.
. Chatzky and Tedder are no longer working together or law partners, Tr. Trans. 1136:15-1137:2 (Chatzky testifying that he had ended his partnership with Tedder by February 22, 1996). Chatzky's firm has been retained by this time to represent the Wylys. IRS Ex. 108 (fax from French to Chatzky dated February 1, 1996 discussing Chatzky’s fee structure).
.See Wyly Ex. CK.
. Wyly Ex. CB at SWYLY005378.
. See pp. 482-88, supra.
. See Wyly Ex. CE.
. SEC Trial Tr. 3751:24-3752:4, 3752:15-18 (French); IRS Ex. 806 at WYLY-SEC00010968 (February 16, 1994 memorandum from Lubar to French “Re: Foreign Trusts” in which Lubar states opines that trusts settled by nonresident aliens — i.e., King and Cairns — "will be ‘grantor trusts’ for all U.S. federal income tax purposes ... [but] because the Grantor [King and/or Cairns] is a nonresident alien as to the United States..., the Grantor will have no actual U.S. tax liability or obligation to file a U.S. income tax or information return.”). Although it was re-characterized by the SDNY Court as a foreign grantor trust as to Sam in the SEC Action.
. See Wyly Ex. CF.
.SEC Trial Tr. 3751:24-3752:4, 3752:15-18 (French); IRS Ex. 806 at WYLY-SEC00010968 (February 16, 1994 memorandum from Lubar to French "Re: Foreign Trusts” in which Lubar states opines that trusts settled by nonresident aliens — i.e., King and Cairns — "will be ‘grantor trusts’ for all U.S. federal income tax purposes ... [but] because the Grantor [King and/or Cairns] is a nonresident alien as to the United States..., the Grantor will have no actual U.S. tax liability or obligation to file a U.S. income tax or information return.”). Although, once again, the SDNY Court recharacterized the La Fourche IOM Trust as a foreign grantor trust as to Sam in the SEC Action.
. Each entity issuing a private annuity— whether in 1992 or in 1996 — received an opinion from Chatzky and Associates dated April 15, 1998 addressing "the impact that Income Tax Regulation Section 1.1001-3 has on the modification of a private annuity agreement issued by you....” See, e.g., Wyly Ex. CS at SWYLY002638. This opinion was apparently requested because Sam amended the annuity agreements to defer the commencement date of his receipt of annuity payments. The upshot of these opinions is that (i) "it is unlikely that the modification of the timing of the private annuity payments will be considered a modification of a ‘debt instrument,' ” id. at 2643, and (ii) "it is likely that the Private Annuity will not be a debt instrument for purposes of Internal Revenue Code Section 1001, and thus this significant modification of a debt instrument analysis will be inapplicable to the transaction," id. at 2655. The other eleven opinion letters are identical except that the addressee is changed to be another of the IOM corporations issuing an annuity to Sam or for his benefit. See Wyly Exs. CT, CU, CV, CZ, DA, DB, DD, DH, DJ, DK, and DL. These twelve opinion letters have no effect on the above analysis of Sam’s reasonable cause and good faith defense.
. SEC Tr. Trans. 1707:2-4 (French).
. Id. at 3758:7-8 (French).
. Mediaworks, Inc. v. C.I.R.,
. See, e.g., Hermax Co., Inc. v. C.I.R.,
. Mayflower Inv. Co. v. C.I.R.,
. See Whitehouse Hotel Ltd. P'ship,
. Klamath,
.
. Id. at 97-99.
. Id. at 99.
. Id.
. Id. at 99-100.
. Id.
. Id.
.
. Id. at 166.
. Id.
. Id.
. Id. at 168-69.
. Id.
. Id. at 169. Although not relevant here, Son of BOSS is a type of tax shelter that was designed and promoted by tax advisors in the 1990s to reduce federal income tax obligations on capital gains from the sale of a business or other appreciated asset. It’s informal name comes from the name of an earlier tax shelter, BOSS ("Bond and Option Sales Strategy”) that it somewhat resembled.
. Id. at 170.
. .Id. at 171.
. Id.
. Id.
. Id. at 182-83.
. Id. at 223.
. Id. at 223-24.
. Id. at 225.
. Id. at 225-26.
. Id. at 226.
. French also asked one of his partners at Jackson Walker, Larry Bean (“Bean”), about Tedder's proposed offshore annuity transactions and the tax consequences flowing from them to the Wylys. Bean advised French that Jackson Walker would not give the Wylys an opinion consistent with that the Wylys were to get from Tedder, but that Tedder's proposéd scheme “may work,” characterizing it, however, as aggressive, SEC Tr, Trans, 3725:6-3727:6, 3737:43741:12 (French). Three things of significance flow from this: (i) once again, French himself was not competent to analyze the tax .consequences, (ii) French's own law firm was unwilling to give the Wylys’ a favorable legal opinion upon which they could rely with respect to the 1992 IOM trusts and annuity transactions, and (iii) Sam knew that his primary outside law firm, Jackson Walker, would not give him a legal opinion corroborating the opinion he expected to receive from the promoter of the offshore system — i.e., Tedder’s law firm — prior to establishing the 1992 IOM trusts and undertalcing the 1992 private annuity transactions.
. Tr, Trans. 547:5-12 (Evan) ("I've known Mike a very long time, Probably since the early 1980s he’s been involved as the attorney for the family. Early on it was primarily related to securities. With the public companies and mergers and acquisitions and a lot of corporate finance activities, he was very busy with many of the companies that the family was involved in, but then also with just giving advice to the family on other activities.”), 550:4-14 (Evan) (Mike French was “the general counsel of Maverick Capital as well as the general counsel for the family.”), 1394:16-24(Sam) (testifying French was primarily a securities lawyer); SEC Tr. Trans. 2116:12-20 (French testifying that he was not a tax lawyer, but that as of 1991 he had been practicing securities law for about 20 years).
. SEC Tr. Trans. 1707:2-4 (French).
. Id. at 3758:7-8 (French).
. Tr. Trans. 1394:16-24(Sam).
. SEC Tr. Trans. 3742:8-22 (French testifying that he went to visit Lubar in 1993 regarding the 1992 trusts), 3709:183711:20 (French testifying that he consulted with Lu-bar again in 1997. Although French’s testimony in the SEC Action indicates that French reached out to Lubar at least in part to see if Morgan Lewis would represent the Wylys in an audit unrelated to the offshore system, the grantor status of the 1992 trusts was still also clearly on French’s mind. A portion of French’s testimony in the SEC Action that was admitted as evidence in this proceeding discusses a fax written by Lubar on June 4,
.Tr. Trans. 709:1-20 (Sam explaining how French was charged to oversee the legal specialists hired to establish the trusts), 703:11-25 (Sam explaining that "he [French] was sort of the coordinator or the commander of the lawyers who — who worked on it” while Sam considered himself more the “leader of the companies."), 548:13-16 (Evan discussing how French would seek out other attorneys to give advice — "So Mike would be kind of the lead, but he would bring in whatever specialist he needed. And if there wasn't someone at Jackson Walker that could do it, then he would bring in, you know, an outside attorney.”).
. No doubt prompted in part by French's view of Tedder as something of a “hustler.” SEC Trial Trans. 3773:5-11.
. Tr. Trans. 1394:16-24(Sam).
. Id. at 2116:12-14 (French); see also id. at 3758:7-8 (French) (“I’m not the tax lawyer. I'll take that disclaimer again, okay.”).
. SEC Tr. Trans. 1725:9-1729:7, 2067:7-2068:22, 2113:11-2116:20 (French’s testimony describing a memo analyzing various securities law issues related to the then-proposed offshore system), 1761:22-1765:17 (French
.Tr. Trans. 699:15-21(Sam) ("Q. Okay. What role did Mr. French play in setting up the Isle of Man trusts? A. Well, he was the chief — chief lawyer, chief architect, who — I mean, there were others who worked on it, but he was the — I would say the leader of a team of lawyers and certified public accountants who worked on it.”), 709:1-20 (Sam explaining how French was charged to oversee and recruit the legal specialists hired to establish the trusts), 703:1125 (Sam explaining that "he [French] was sort of the coordinator or the commander of the lawyers who— who worked on it,” while Sam considered himself more the "leader of the companies.”), 547:25-548:23, 553:11-554:15 (Evan) (French was a competent, trusted attorney and the lead person on legal matters for the Wylys but often brought in specialists), 590:22-591:21 (Evan) (Sam "felt like Mike, you know, not only evaluated it from his own perspective, but brought in whatever experts from whatever firm — whether it was Jackson Walker, Jones Day, whether it was other attorneys, Tedder, or Chatzky — Sam relied on Mike, and I relied on Mike, you know, to be our attorney and to look out for our best interest and to make sure we were doing what was legal and appropriate and right.”); SEC Tr. Trans. 1957:21-1958:8 (French) ("Q [by Wyly counsel], When Mr. Sam Wyly got married to Cheryl Wyly, his current wife — that happened like in '94, right? A. I don’t remember what year it was. Yes. Q. — he turned to you to help him get the prenuptial agreement, right? A. He asked me to get one. I got another lawyer to do it. Q. Mr. Wyly, when he needed something very personal like that, would turn to you. You weren’t a family lawyer, Not for you to do it, but to go get some other lawyer to do it, right? A. Yes. Q. You acted kind of as his interface with other lawyers? A. Yes.”).
. See Tr. Trans. 709:l-20(Sam); 547:25-548:23, 553:11-554:15, 590:22-591:21 (Evan testifying that Sam relied upon French "as general counsel”); SEC Tr. Trans. 1957:21— 1958:8 (French).
. CNT Investors, LLC,
. SEC Tr. Trans. 1717:1-1719:17 (French describing Tedder’s foreign trust presentation), Tr. Trans. 1050:191051:16 (Sam describing meeting with Tedder where Tedder explained what would become the offshore system); 1052:9-1059:ll(Sam) (same).
. IRS Ex. 806 (Memorandum dated February 16, 1994; from Lubar to French providing advice on the creation of foreign grantor trusts to non-resident aliens of the United
. Tr. Trans. 566:4-9 (Evan).
. Tr. Trans. 565:22-566:13 (Evan testifying regarding French's role double-checking transactions), 572:4-6 (Evan) ("Q. Do you recall Mr. French ever advising your father or you not to create the ’92 Isle of Man trusts? A. No. In fact, he recommended it.”), 568:19-569:25 (Evan stating that he understood that French was researching the 1992 trusts and that — as the family’s general counsel — he was the primary liaison between the Wyly family and Tedder and Chatzky), 582:11-583:1 (Evan), 586:15-587:11 (Evan), 588:4-18 (Evan stating that French never told Charles, Sam, or him that the IOM trusts were somehow illegal, wrong, or improper; and that the Wylys were comforted by the fact that French and some of his partners setup their own IOM trusts), 701:24-702:3 (Sam stating that French and Robertson — after attending Tedder’s seminar in New Orleans— told Sam that they "thought it was a good plan.”). Interestingly, however, French repatriated his Isle of Man trust in 2002. SEC Tr. Trans. 1913:9-1915:19 (French).
. As Sam’s eldest son, Evan has an interest in seeing that Sam’s liability is minimized here. Moreover, Evan established his own IOM trust in 1996, and the outcome here may indirectly implicate the tax (and reporting) consequences to him of transactions he undertook through that trust. Tr. Trans. 589:9-590:10 (Evan), 660:25-664:6 (Evan); 774:9-25 (Evan testifying that he performed annuity transactions through his own IOM trust — Ginger Trust — five years after 1991 — z.e. in 1996).
.SEC Tr. Trans. 3738:12-14 (French) ("[Bean] thought that it might work, I believe. That was his take on it. Now, he also indicated to me, and I’ve said that before, that he felt like it was aggressive.”); IRS Exs. 130, 1199 ¶ 10 (p. 7) (Annex A, Admissions of Defendant Michael C. French), which consists of admissions that French made in connection with the SEC Action and which were separately admitted as evidence in this proceeding, and which read in pertinent part as follows: "... Tedder provided a tax opinion in connection with the Wylys' proposed use of Isle of Man Trusts, which stated in substance that the securities held by the Trusts would not be subject to U.S. taxes. French ásked a tax lawyer at Jackson Walker [Bean] to review the opinion and the lawyer subsequently informed French that the position taken in the opinion was aggressive, and that Jackson Walker would not.be willing to issue a similar
.IRS Ex. 806 (Memorandum from Lubar to French providing Lubar’s advice predicated on facts French told him to assume were true, but were not); Cairns Depo Tr. 46:18— 47:4, 158:6-7 (Cairns testifies that French prepared a letter stating Cairns was a friend of Sam’s, and that this was false). See also IRS Ex. 92 (Cairns letter). See also pp.415-23, supra.
. SEC Tr. Trans.l917:2-9, 1921:3-7, 1940:14-1941:5, 1952:24-1954:21 (French).
. Id. at 1917:2-16 (French).
. Id. at 2116:12-14 (French); see also id. at 3758:7-8 (French) ("I’m not the tax lawyer. I’ll take that disclaimer again, okay.”).
. Computation Stipulations ¶ 3.
. Id. ¶ 15.
. See 26 C.F.R. § 25.2511-1 (Transfers in general); Dickman v. C.I.R.,
. 26 C.F.R. § 25.2512-8 (Transfers for insufficient consideration).
. Harwood v. C.I.R.,
.
. Wheeler v. U.S.,
. Debtors’ Pre-Trial Brief [ECF No. 1015] ¶ 32 (citing Guest v. C.I.R.,
. See Security Indus. Ins. Co. v. U.S.,
.
. Id. at 544.
. Southgate Master Fund, L.L.C.,
. Stobie Creek Inv. LLC,
. Klamath,
. Southgate Master Fund, L.L.C.,
. Id.
.
. Id. at 491 (footnotes and internal quotations omitted).
.
. Id.
. Id. (emphasis deleted) (citations and internal quotations omitted).
. Joint Stipulations ¶36. Joint Exs. 11-16 (Certificate of Incorporation, Memorandum of Association, and Articles of Association for each of Orange, FloFlo, Bubba, Pops, Balch, and Katy, respectively).
.Tr. Trans. 625:23-626:18 (Evan), 2090:12-2091:15 (Hennington). Although the Court questions why Evan, who had a Harvard MBA and had already established his own investment fund, would need a Cayman LLC to help "educate” him as to how foreign trusts and investments worked. See id. 523:23-524:2, 679:4-8 (Evan).
. Joint Stipulations ¶¶ 292, 303-305.
. The Bulldog IOM Trust owns each of these IOM corporations, except for Yurta Faf Limited (IOM), which is owned by the Bessie IOM Trust, Joint Stipulations ¶¶ 21, 36.
. Greenbriar Limited (IOM) was established under the Delhi IOM Trust. Joint Stipulations ¶ 27.
. Joint Stipulations ¶ 292. East Baton Rouge Limited (IOM) and East Carrol Limited (IOM) are parties to 1992 annuity transactions, id. ¶¶ 119-122, while Moberly Limited (IOM) and Yurta Faf Limited (IOM) are parties to 1996 annuity transactions, id. ¶¶ 137-138, 141-142.
. Id. ¶ 303.
. Id. ¶ 304.
. Wyly Exs. 89 (showing which LLC corresponded to which child), 90 at SEC100066426 (showing the allocation of assets among the Cayman LLCs).
. IRS Ex. 90 at SEC100066424.
. Joint Exs. 11-16 (formation documents).
. See also Wyly Ex. G (financial statements for Cayman LLCs).
. Wyly Ex. KW at SWYLY012939 (graphic depicting ownership structure for personal use real estate); see, e.g., Memorandum Opinion Exhibits D-H (showing ownership structures).
. Joint Stipulations ¶¶ 44-47; IRS Ex. 90. The record shows that some percentage of Mi Casa Limited (IOM) was transferred from Bessie IOM Trust to FloFlo in 2001; however, the record does not disclose when that transfer occurred or what percentage was transferred. See Tr. Trans. 2519:24-2520:13 (Bennington); IRS Ex. 90 (showing allocation of assets); Wyly Ex. G at HST-PSI230998 (financial statement showing FloFlo holding an interest in "Mi Casa Limited" as of December 31, 2001).
. Wyly Ex. KW at SWYLY012943 (graphic depicting ownership structure for business use real estate); see, e.g., Memorandum Opinion Exhibit E (showing ownership structure).
. See Wyly Exs. N (showing Kelly as the manager of Cottonwood Ventures I LLC (Colorado), the domestic LLC owned by the domestic corporation and the S corporation); Joint Stipulations ¶¶ 322-326 (detailing ownership structure). See also Memorandum Opinion Exhibit E.
. Tr. Trans. 2540:1-2550:10 (Pulman) (describing general structure of real estate transactions); Wyly Ex, KW (Meadows Owens’ internal memorandum detailing ownership structure for real estate, both business use and personal use).
. Tr. Trans. 2540:20-2541:6 (Pulman).
. Id. 2541:4-15 (Pulman).
. Id. 2541:20-2542:1 (Pulman).
. See, e.g., id. 2540:1-2543:10 (Pulman) (discussing concept in relation to . the Woody Creek Ranch Management Trust); Wyly Ex. BG (Mi Casa Management Trust) § 2.1 (“This Trust is expressly designed to be a Grantor Trust, for purposes of Sections 671 through 679 of the Code, and as such will be ignored for Federal income tax purposes as an entity separate from its Grantors. Therefore, the Trust Estate will be deemed to be owned by Grantors as tenants in common, each owning an undivided interest in the Trust Estate...,).
. Tr. Trans. 2542:4-24 (Pulman).
. Rosemary Acton was the mother of Evan, Lisa, Laurie, and Kelly. She lived in the home until her death. The home is now occupied by Evan’s daughter, McCary. Tr. Trans. 677:ll-12(Sam); 1557:4-25 (Laurie); 2298:14-24 (Hennington).
. Allocation regarding Two Mile Ranch was split evenly among all six children. IRS Ex. 90. However, only Lisa, Laurie, and Kelly built homes on the property. Tr. Trans. 931:17-932:19 (Evan); 1514:24-1515:2 (Laurie) ("I live in a house here in Dallas on Crooked Lane that is owned by — by an Isle of Man trust, and I also have a second home I— that I go to in Colorado on the ranch). The record is unclear, however, whether there was a shared home or multiple homes.
. Tr. Trans. 1549:5-1550:2 (Laurie) (“Well, the concept was that Dad’s kids could build property on — building on that property in Colorado, and each was allowed a certain amount. And I reasoned, well, I'm not in Colorado year-round. I wonder if I could do the same concept in Dallas where I live.”).
. Id. 1551:11-1552:25 (Laurie).
. Id. 1552:11-22 (Laurie).
. Joint Stipulations ¶ 457; Wyly Ex. BG (Trust Agreement).
. Tr. Trans. 1550:18-1551:10 (Laurie).
. Although the record does not divulge exactly how much in offshore funds were used to build the Mi Casa home, FloFlo’s financial statements appear to value the home at a book value of $3,215,000 as of November 30, 2015. Wyly Ex. G (Financial Statements) at HST-PSI230623 (showing FloFlo holding a loan or account receivable from Mi Casa Limited IOM of $3,215,000. Since the record does not reflect such a loan or account receivable, the Court reasonably infers that the figure reflects the value allocated to the home).
. IRS Ex. 90.
. Tr. Trans. 2296:6-9 (Hennington); see abo Wyly Ex. G (Financial Statements) at HST-PSI230998 (showing FloFlo holding an investment in "Mi Casa Limited” as of December 31, 2001).
. Wyly Exs. BG (Mi Casa Management Trust) at § 1,5 (showing Laurie as the initial trustee) and BH (Articles of Organization of Mi Casa, LLC) at Article V (showing Laurie as the manager).
. Tr. Trans. 1557:7-1558:12 (Laurie); IRS Ex. 87 at WYLYSEC01112940 ("Evan, Lisa, Laurie and Kelly are planning to purchase a house for their mother using off-shore funds. 1 think we would like to use the same Texas LLC, Texas Trust and off-shore corp. to get this done.”).
. Joint Stipulations ¶ 466; Wyly Ex. BK (formation documents); Tr. Trans. 2282:25-2283:2 (Hennington).
. Joint Stipulations ¶ 46.
. IRS Exs. 89, 90.
. Wyly Exs. BK (The Spitting Lion Management Trust) at § 1.5 (showing Rosemary Acton and Lisa as the initial trustees); BL (Articles of Organization of Spitting Lion, LLC) at 2 (showing Rosemary Acton and Lisa as the initial managers).
. Tr. Trans. 1567:7-13 (Laurie).
. See Memorandum Opinion Exhibit G.,
. Tr. Trans. 931:7-932:15 (Evan), 1550:4-8 (Laurie). The testimony is clear that Laurie built a second home on the ranch; however, it is unclear whether each of Lisa and Kelly built a home or whether they share a home.
. Joint Stipulations ¶ 47; IRS Ex. 90.
. Joint Stipulations ¶ 321.
. Id. ¶ 44.
. Id. ¶ 322; Wyly Ex. N (Articles of Organization file stamped July 26, 2000). But see Wyly Ex. O (Operating Agreement of Cottonwood Ventures I, LLC dated as of August 1, 2000).
. Wyly Ex. M (Warranty Deed).
. Joint Stipulations ¶¶ 324-325; Wyly Exs. N (Articles of Organization for Cottonwood Ventures I, LLC), O (Operating Agreement of Cottonwood Ventures I, LLC) at SWY-LY053020 (showing contribution percentages), P (Articles of Incorporation of Wyly Works, Inc. (Texas)).
. Joint Stipulations ¶¶ 44; IRS Exs. 89, 90.
. Computation Stipulations ¶ 4 (setting forth the amounts by tax year).
. Joint Stipulations ¶ 45; Wyly Ex. T (Articles of Organization).
. Id. ¶ 342; Wyly Ex. T (Articles of Organization file stamped July 26, 2000). But see Wyly Ex. U (Operating Agreement of Cottonwood Ventures II, LLC dated as of August 1, 2000).
. Wyly Ex. S (Warranty Deed).
. Joint Stipulations ¶ 45.
. IRS Ex. 90.
. Wyly Ex. U (Operating Agreement of Cottonwood Ventures II, LLC) at SWYLY053079 (Kelly and Sam signing as managers).
. Computation Stipulations ¶ 5 (setting forth the amounts by tax year),
. Tr. Trans. 2092:14-18 (Hennington) ("Did any of the six children receive any of the liquidation proceeds from the Cayman Islands companies when they were liquidated? No. I would know that because I do all of the accounts for the children,”).
. Id. at 2091:6-2092:8, 2295:3-20, 2519:14-2521:5 (Hennington).
. Id. at 2295:3-20 (Hennington).
. Id. at 3992:25-3993:7 (Messersmith) ("when that money hits Cottonwood Ventures I LLC, that is the time at which the gift occurs, but the gift is to Kelly Wyly because she was the one controlling the LLC and all aspects of the operation”).
. Id. at 3997:21-25 (Messersmith) ("The gift is when the money hits Cottonwood Ventures II LLC, and that was for the benefit — • actually, it ended up being allocated among all six of the children — so — yes, all six of the children”).
. Id. at 4001:8-10 (Messersmith) ("The gift is the amount of money that Sam Wyly funded each of these LLCs with or the value of the assets that — that were put in.”).
. See Joint Stipulations. ¶¶ 332-341 (detailing the direct and indirect transfer of funds to Cottonwood Ventures I LLC (Colorado) from Wyly Works, Cottonwood Gallery Inc. (Nevada), Cottonwood I Limited (IOM), Greenbriar Limited (IOM), and Audubon Asset Limited (IOM)) and ¶¶ 350-377 (detailing the direct and indirect transfer of funds to Cottonwood Ventures II LLC (Colorado) from Sam, Kelly, Cottonwood II Limited (IOM), Cottonwood Management Trust (US), Greenbriar Limited (IOM), Yurta Faf Limited (IOM), and Sarnia Investments Limited (IOM)).
. Debtors’ Pre-Trial Brief [ECF No. 1015] ¶ 32 (citing Guest v. C.I.R.,
. Id. ¶ 37.
.
. Id. at *3.
. Id. (citing cases).
. Id. at *4. The Debtors also cite to Jordahl v. C.I.R.,
. 26 C.F.R. § 25.25ll-2(b).
. See pp. 389-461, supra.
. 26 C.F.R. § 25.25ll-2(b).
. Holmes v. C.I.R.,
. Although the Cottonwood Ventures II property was allocated to each of Sam's six children, the record shows that Kelly is the only child who made a financial contribution to Cottonwood II Management Trust (US). Joint Stipulations ¶ 350. Sam also made a small financial contribution to Cottonwood II Management Trust (US). Id.
.See Wyly Exs. 0 (Operating Agreement of Cottonwood Ventures I, LLC) at Article VIII (Company Profits, Losses, and Distributions), V (The Cottonwood Ventures II Management Trust) at Article II (Management,
. Wyly Ex, M (Warranty Deed).
. Wyly Ex. O § 1.12(n) & p. 40 (showing Kelly signing as Manager); Memorandum Opinion Exhibit E.
. Joint Stipulations ¶ 324.
. Wyly Ex. 0§ 3.1(b).
. Id, § 3.2(a).
. Id. § 3.5; see also id. §§ 3.3, 3.4, 3.6.
. Id. at Ex. A ("Contributions); Memorandum Opinion Exhibit E.
. Id. § 3.
. Wyly Ex. R § 5.05 ("Any officer or agent elected or appointed by the Board of Directors may be removed at any time by the affirmative vote of a majority of the Board of Directors. Any vacancy occurring in any office of the corporation may be filled by the Board of Directors.”).
. Id. § 3.02 ("The Shareholders shall have the right at any special meeting to remove any Director of this corporation, with or without cause by majority vote of the issued and outstanding shares of capital stock entitled to vote on the election of Directors.”).
. Joint Stipulations ¶ 326; Memorandum Opinion Exhibit E.
. Joint Stipulations ¶ 44; Memorandum Opinion Exhibit E. Although the evidence shows that at some point Bubba was transferred at least some interest in Cottonwood I Limited (IOM) in 2001, these shares were returned to Bessie IOM Trust in 2006. Id. In addition, the evidence in the record shows that such appointments to the Cayman LLCs were not "formal appointments out of the overall trust and will be revocable. They exist as a sub-fund via an informal understanding with the trustee whereby we account for these entities separately and liaise with particular family members regarding the underlying assets.” IRS Ex. 90 at SEC100066424. In addition, Bessie IOM Trust wholly owned these Cayman LLCs. Memorandum Opinion Exhibit B.
. Wyly Ex. S (Warranty Deed).
. Wyly Ex. U (Operating Agreement of Cottonwood Ventures II, LLC) § 1.12(g) & p. 18 (showing Kelly and Sam as Managers).
. Id. §§ 1.12(h), 2.1, & p. 18 (showing Cottonwood II Management Trust (US) as the "original Member entitled to vote”).
. Id. § 3.1(b).
. Id. § 3.2(a).
. Id. §§ 3.3, 3.4, 3.5, 3.6.
. Id. at 18 (reflecting Highland Trust Company as trustee of the Cottonwood Ventures II Management Trust); Wyly Ex. V (The Cottonwood Ventures II Management Trust) § 1.5. Hennington, the CFO of the Wyly family office, signed documents on behalf of Highland Trust Company. See e.g., Wyly Ex. U at 18 (showing Hennington signing as the "Authorized Officer” of Highland Trust Company).
. Wyly Ex. V at § 1.5(a).
. Id. § 1.3(a).
. Joint Stipulation ¶ 45; Memorandum Opinion Exhibit F. Although the evidence
. Wyly Ex. V §§ 1.5(a) ("Any Trustee may be removed ... by the following individual^) and entity(s) ... [1] by SAM and/or KELLY if either is living and competent, and the Corporation”), 1.5(a) (defining Corporation as Cottonwood II Limited (IOM)).
.
. Id.
. Id.
. Southgate Master Fund, L.L.C.,
. Klamath,
. See, e.g., Tr. Trans. 1549:5-1550:2 (Laurie) ("Well, the concept was that Dad's kids could build property on — building on that property in Colorado, and each was allowed a certain amount. And I reasoned, well, I’m not in Colorado year-round. I wonder if I could do the same concept in Dallas where I live.”); IRS Ex. 87 at WYLY-SEC01112940 ("Evan, Lisa, Laurie, and Kelly are planning to purchase a house for their mother using offshore funds. I think. we would like to use the same Texas LLC, Texas Trust and off-shore corp. to get this done.”).
. Joint Stipulations ¶¶ 43-47. The Court notes that the parties stipulated that, as of April 11, 2000, Rosemary’s Circle R Ranch Limited (IOM) was owned by the Bessie IOM Trust and Orange. Id. ¶ 47. There is no explanation in the record, though, how Orange could hold an interest in Rosemary Circle R Ranch Limited (IOM) in April 2000, when it was not established until June 1, 2001. Id. ¶ 36. The Court assumes the earlier stipulation to be in error.
. Id. ¶ 36.
. IdA 46.
. Id. ¶ 44.
. Id. ¶ 45.
. Id. ¶ 47.
. The record shows that some percentage of Mi Cása Limited (IOM) was transferred from the Bessie IOM Trust to FloFlo in 2001; however, the record does not disclose when that transfer occurred or what percentage was transferred. See Tr. Trans. 2519:24-2520:13 (Hennington); IRS Ex. 90 (showing allocation of assets); Wyly Ex. G at HST-PSI230998 (financial statement showing FloFlo holding an interest in “Mi Casa Limited” as of December 31, 2001).
. As found by the SDNY Court in the SEC Action, to which we have applied collateral estoppel effect here. Collateral Estoppel No. 24.
. As reflected in the record: (i) the Cayman LLCs were established June 1, 2001 and were wholly-owned by the Bessie IOM Trust, Joint Stipulations ¶ 36, (ii) the Mi Casa, Spitting Lion, Cottonwood Ventures I and II, and Rosemary Circle R Ranch properties were purchased prior to June 1, 2001, Wyly Exs. BJ, BN, K, L, M, and S and Joint Stipulations ¶ 307, (iii) each IOM Real Estate Company was wholly-owned by the Bessie IOM Trust as of its formation, other than Rosemary Circle R Ranch Limited (IOM), which was owned by the Bessie IOM Trust and Orange as of April 11, 2000, Joint Stipulations ¶¶ 43-47, and (iv) as of June 1, 2001, the IOM Real Estate Companies were owned wholly or partially by the various Cayman LLCs, Joint Stipulations ¶¶ 44-47 (although ¶ 44 states "as of June 1, 2002,” that date appears to be in error; the date, however, does affect this Court’s ruling). Although the record shows that some percentage of Mi Casa Limited (IOM) was transferred from Bessie IOM Trust to FloFlo in 2001, the record does not disclose exactly when that transfer occurred or what percentage was transferred. See Tr. Trans. 2519:24-2520:13 (Hennington); IRS Ex. 90 (showing allocation of assets); Wyly Ex. G at HST-PSI230998 (financial statement showing FloFlo holding an interest in "Mi Casa Limited” as of December 31, 2001).
. The Bessie IOM Trust owned: (i) Spitting Lion Limited (IOM) indirectly (through its ownership of Orange, Pops, FloFlo, and Bubba), (ii) Cottonwood I Limited (IOM) directly in part and indirectly in part (through its ownership of Bubba), (iii) Cottonwood II Limited (IOM) directly in part and indirectly in part (through its ownership of the Cayman LLCs), (iv) Rosemary Circle R Ranch Limited (IOM) directly in part and indirectly in part (through its ownership of the Cayman LLCs), and (v) Mi Casa Limited (IOM) directly in part and/or indirectly in part (as the record is unclear).
. IRS Pre-Trial Brief [ECF No. 1018] at 78 ("Additionally, each child had full control of the entities that directly owned the property. The ‘debts' were also transferred to the Cayman LLCs which were created for the. benefit of children, showing the donative nature of the transactions involving Cottonwood I and II and the Cayman LLCs. * * * The listing of these obligations in the family finan-cials records was not a sign of an actual debt, but rather to show to whom the property was assigned. This is reflected in the transfer of these 'loans’ to the Cayman LLCs, which were created for the benefit of the children. Each Cayman LLC would receive the "loans” associated with the assets that they were using i.e. Cottonwood I to Bubba, LLC and Mi .Casa to FloFlo, LLC.”)
. As clearly shown in the record, the interests in the IOM Real Estate Companies transferred to the Cayman LLCs were returned to the Bessie IOM Trust when the Cayman LLCs were liquidated, which is directly contrary to the IRS’ allegation that the interests were gifted by Sam to his children.
. Joint Stipulations ¶¶ 292-304; Computation Stipulations ¶ 6.
. Computation Stipulations ¶ 6. The Court is unsure whether the parties’ stipulated figure is inclusive or exclusive of the ownership interests in the IOM Real Estate Companies. That determination is irrelevant, however, since the Court finds that no gift occurred in either instance.
. IRS’ Amended Proposed Findings of Facts and Conclusions of Law [ECF No. 1103] ¶ 97.
.
. IRS' Amended Proposed Findings of Fact and Conclusions of Law [ECF No. 1103] ¶ 97.
. Id.
. Computation Stipulations ¶ 15.
. Joint Stipulations ¶ 378.
. IRS Ex. 1281 at CWG-000340 (section titled "Sport Horses”). See also Memorandum Opinion Exhibit I.
. See Wyly Ex. KZ at SWYLY013139 (illustrating the ownership structure); Tr. Trans. 2553:14-2555:23 (Pulman discussing the ownership structure and related tax implications).
. Joint Stipulations ¶ 87.
. Id. ¶ 387.
. Id. ¶¶ 380, 384. The agreed demonstrative chart provided to the Court, however, shows that Stargate Sport Horses, LP (Texas) was owned 91.21% by Stargate Horse Properties, Inc. (Nevada) and 8.79% by Stargate Sport Horse Management LLC (Texas), which are the same percentages reflected in the Agreement of Limited Partnership of Stargate Sport Horses, L.P. (Wyly Ex. X at 39). Although the Court notes this discrepancy, it is not material to its decision.
. Wyly Ex. Y (General Warranty Deed).
.Joint Stipulations ¶ 379.
. M. ¶ 390.
. Id. ¶¶ 391-409.
. Computation Stipulations ¶ 16 (transfers by tax year)'.
. Tr, Trans. 2184:13-19 (Hennington); Wyly Ex. X (Agreement of Limited Partnership of Stargate Sport Horses, L.P.) at Article IV (Capital Contributions).
. Tr. Trans. 2184:20-2185:9 (Henning-ton).
.' Id. at 2185:14-19, 2186:4-2187:20 (Hen-nington). See also Wyly Ex. X (Agreement of Limited Partnership of Stargate Sport Horses, L.P.) at § 11.02 (Method of Liquidation).
. Tr. Trans. 2187:16-20 (Hennington).
. Id. at 3982:4-8 (Messersmith) ("The gift occurred when the money hit the LP, but— because that's when Emily got control, but the gift is to Emily, but the gift did not occur until the money hit the LP.”).
. Joint Stipulations ¶ 434.
. Id. ¶ 437; Wyly Ex. BC at SWY-LY053239 (Articles of Organization file stamped October 22, 1999); but see Wyly Ex. BC at SWYLY053271(Operating Agreement of Little Woody, LLC (Colorado) dated as of November 30, 1999).
. Joint Stipulations ¶ 437. Although'the Joint Stipulations state that Little Woody, LLC was formed in Texas and refers to the entity as "Little Woody, LLC (Texas),” the entity was formed in Colorado. Wyly Ex. BC (Articles of Organization and Operating Agreement of Little Woody LLC). Thus, it appears to the Court that the Joint Stipulations’ references to Texas in paragraphs 437, 438, 440, 442-445, and 448-455 are in error.
. Id. ¶ 439.
. Id. ¶ 440.
. Id. ¶ 442. See also Exhibit J attached hereto.
. Tr. Trans. 2187:21-2188:7 (Henning-ton).
. Joint Stipulations ¶ 447.
. Id. ¶¶ 449-455 (detailing transfers by date).
. Tr. Trans. 3987:1-6 (Messersmith) ("The gift is actually made, though, at the point the funds hit Little Woody, LLC, because that’s when they had control of it.”). The Court notes, however, that Emily and Jennifer have no direct ownership of Little Woody LLC (Colorado). Instead, they are each 1% co-grantors of the Little Woody Management Trust (US), the direct parent of Little Woody LLC (Colorado).
. Computation Stipulations ¶ 17 (transfers by year); Joint Stipulations ¶¶ 448-455 (detailing specific transfers).
. Debtors’ Pre-Trial Brief [ECF No. 1015] ¶ 32 (citing Guest v. C.I.R.,
. See, e.g., Collateral Estoppel Nos. 52, 53.
. In short, (i) Charles had total control over Stargate Farms Limited (IOM) through his control over the trustee of the Tyler IOM Trust (see Collateral Estoppel Nos. 52, 53; Joint Stipulations ¶ 87), which (ii) had total control over the appointment of the officers and directors of Stargate Horse Properties Inc, (Nevada) (see Wyly Ex. AC (Bylaws of Stargate Horse Properties, Inc. (Nevada) at §§ 5.01 & 5.02 (stating chairman of the board or, if no chairman, president has operational control over the business), 3.2 & 5.02 (the shareholder has the ability to appoint and remove officers and reconstitute the board of directors); Joint Stipulations ¶ 387 (Stargate Horse Properties, Inc, (Nevada)’s sole shareholder is Stargate Farms Limited (IOM)), which (iii) in turn, had total control over the management of Stargate Sport Horses LP (Texas) (see Wyly Ex. X (Agreement of Limited Partnership of Stargate Sport Horses, L.P.) at §§ 6,01 (placing management of the business, including the right to sell assets, with the Managing General Partner), 10.02-10,03 & 1.01 (the Managing General Partner may be removed with the written consent of limited partners holding at least 50% of sharing ratio, as judged by investment capital), Ex. A (showing Stargate Horse Properties, Inc. as holding an Initial Sharing Ratio of 91.21%); which (iv) in turn had control over the management of Stargate Horse Farm (see Joint Stipulations ¶ 378).
.Tr. Trans. 2187:16-20 (Hennington).
. A copy of the Little Woody Management Trust (US) agreement may be found at Wyly Ex. BD.
. Tr. Trans. 2187:16-20 (Hennington).
. See p. 540 n. 1081, supra.
. Joint Stipulations ¶ 447-555.
.Id. ¶11439-442; Memorandum Opinion Exhibit J. Although the Joint Stipulations state that Little Woody, LLC was formed in Texas and refers to the entity as "Little Woody, LLC (Texas),” the entity was formed in Colorado. Wyly Ex. BC (Articles of Organization and Operating Agreement of Little Woody LLC). Thus, it appears to the Court that the Joint Stipulations' references to Little
. Wyly Ex. BC (Articles of Organization of Little Woody LLC) at SWYLY053239 (showing Charles as the sole manager), SWY-LY053271 (Operating Agreement of Little Woody, LLC showing Charles signing as Manager). As reflected in the agreed chart submitted by the parties, Donnie Miller now serves as manager. Memorandum Opinion Exhibit J.
. Joint Stipulations ¶ 442.
. Wyly Ex. BD (The Little Woody Management Trust) at § 1.5.
. Joint Stipulations ¶ 11 ("Mr. French served as primary counsel for Sam Wyly and Charles Wyly until early 2001 when the relationship was severed.”).
. 26 C.F.R. § 25.25ll-2(b).
. Holmes v. C.I.R.,
. Wyly-Ex. OJ (Amendment to Partnership Agreement of Stargate, Ltd) at 2. Documents referencing the formation of SGL vary between using December 14, 1992 and December 15, 1992 as the formation date. The actual date, however, is not material to the Court's analysis and decision.
. Id. § 3.
. Id.
. The ownership percentages are those reflected in an agreed demonstrative chart submitted by the parties. The Court notes, however, that the percentages vary from those set forth in the Amendment to Partnership Agreement of Stargate, Ltd (Wyly Ex. OJ) at § 2.2. The discrepancy is minor and does not affect this Court’s decision.
. Tr. Trans. 2146:10-13 (Hennington) (stating the loans were between 1992 and 1999); Wyly Ex, PD (tracking balance of Unsecured Loan from 1993 through 2011, and showing borrowing- as late as October 2007).
. Schedule F [Case No. 14-35043, ECF No. 351] at 30; Statement of Financial Affairs [Case No. 14-35043, ECF No. 352] at Ex. 3.c.
. Tr. Trans. 2147:9-14 (Hennington). A spreadsheet tracking the Unsecured Loan between March 1993 and December 2011 may be found at Wyly Ex. PD.
. Wyly Ex. OK (Marital Agreement).
. Tr. Tran. 2147:15-21 (Hennington); Wyly Ex. OL (The Caroline D. Wyly Irrevocable Trust). The beneficiaries of the CDW Irrevocable Trust are the children resulting from Dee and Charles’ marriage and all of
. Wyly Ex. ON. The CDW Irrevocable Note required quarterly interest payments. Quarterly principal payments of $651,350 commenced on December 31, 2009, with any unpaid interest and principal due on September 30, 2019. Id. at 1.
. Wyly Ex. OO.
. Wyly Ex. OP at 1.
. See Tr. Trans. 2147:25-2148:11 (Hen-nington); Wyly Ex. OQ (The Charles J. Wyly, Jr. Irrevocable Trust), OR (Memorandum of Sale and Assignment of Partnership Interest), OS (Secured and Partially Guaranteed Promissory Note), OT (Specific Guaranty Agreement), OU (Pledge Agreement).
. The ownership percentages are as reflected on an agreed demonstrative exhibit submitted by the parties, Although the Court was unable to trace these percentages through the documents (Wyly Exs. OJ-OV), the discrepancy was minor and not material to this Court’s decision.
. Wyly Ex, OW (Partnership Agreement for Stargate Investments, Ltd.) § 10.13.
. Id. § 2.2; Joint Stipulations ¶ 162.
. Wyly Ex. OW at Ex A (Initial Capital Contributions).
. In 1992 and 1996, Charles entered into multiple transactions whereby he transferred securities that he had earned from Sterling Software, Sterling Commerce, and Michael Stores in exchange for private annuities payable to Dee and him. See Joint Stipulations ¶¶ 145-160. The private annuities entitled them to contractual payments commencing at various future dates. See pp. 394-408, supra, for a detailed explanation of the annuity transactions.
. Tr. Tran. 2150:1-2151:4 (Hennington); Wyly Ex. OW (Partnership Agreement for Stargate Investments, Ltd.) at Exhibit A; Joint Stipulations ¶ 161.
. Tr. Trans. 2154:1-4 (Hennington).
. Id. at 2154:8-24 (Hennington).
. Id. at 2154:25-2155:10 (Hennington).
. See id. 2154:25-2155:15 (Hennington); Wyly Ex. PC (showing distributions from Stargate Investments (Texas) being paid to "Charles Wyly Community Property”). Because the Revocable Trusts were settled by Dee and Charles, the distributions from Star-gate Investments (Texas) flowed through the Revocable Trusts to Dee and Charles and were reported on their tax returns. 26 U.S.C. § 671; Joint Stipulations ¶ 174.
. Wyly Exs. ON (Dee), OS (Charles); Tr. Tran. 2158:3-2159:6 (Hennington).
. Tr. Trans. 2163:3-13; 2169:8-12, 2171:6-23 (Hennington).
. Id. 2163:18-2173:12 (Hennington).
. See id. 3939:9-11 (Messersmith) ("So the gift is to the irrevocable trust, of which the kids are the sole beneficiaries, but the gift is to the irrevocable trust.”); Computation Stipulations ¶ 18.
. Southgate Master Fund, L.L.C.,
. Wyly Ex. PA at 11 (bank statement).
. Id. at 7 (page titled “Stargate Investments, Ltd. Note Payable 12/31/99 payment”).
. Id.
. Id. at 7, 9, 11.
. Id. at 7, 11, 13.
. Id. at 7, 9, 10.
. Wyly Ex. PC at 1 (showing transferee as “Charles Wyly Community Property”). Although the record reflects that the Revocable Trusts are the sole owners of Stargate Investments (Texas), the distributions from Stargate Investments (Texas) were made directly into Charles and Dee’s community property account because the CDW Revocable Trust is a grantor trust as to Dee and the CJW Revocable Trust is a grantor trust as to Charles, so the distributions would pass through the Revocable Trusts to Dee and Charles, respectively.
.See Wyly Exs. PA, PC, PD. There are instances where the payments are difficult to track, however. For example, Wyly Ex, PA, on pp. 56-57, indicates that a $2.45 million payment was made on the Unsecured Loan on May 5, 2009; however, a review of the attached bank statement does not reflect this payment from Dee and Charles’ account. Nonetheless, according to p. 57, of this $2.45
. This calculation is based upon the pre-Estate Planning Transactions percentages shown on Exhibit K hereto,
. Wyly Ex, PD at 17-19 (showing Dee and Charles’ last payment on the Unsecured Note in October 2010, leaving a loan balance of $25,400,128).
. Statement of Financial Affairs [Case No. 14-35043, ECF No. 352] at Ex. 3,c (showing a $20,000 payment on September 4, 2014). Schedule F, Case No. 14-35043, ECF No. 351 at 30.
. See Klamath,
. Although failure to satisfy this factor alone is sufficient to disregard the transaction for income tax purposes, the Court will nonetheless consider the remaining two Klamath factors, which the Debtor has also failed to satisfy.
. Klamath,
. Wyly Ex. OM (Memorandum of Sale and Assignment of Partnership Interest).
. See Computation Stipulations ¶ 18. Respective counsel for the parties stated on the record that they believed a more precise stipulated amount could , be presented to the Court after entry of this Memorandum Opinion resolving various issues. Thus, a final amount (whether stipulated or as determined by the Court) will be included in the Final Order that will follow the issuance of this Memorandum Opinion.
. See Computation Stipulations ¶ 18.
. The Court notes that the IRS’ Proof of Claim filed against Dee’s estate only references fraud penalties under § 6663 (related to filed returns), not § 6651 (failure to file). At closing argument, however, Dee’s counsel stated that she would not argue that the IRS had waived its right to allege liability under § 6651, Tr. Trans. 4067:11-16 (Ross) ("we’ve decided, based upon the argument today, to just allow [the IRS] to argue whatever gift tax theories they have and not to brief the issue”).
. See Debtors’ Amended Proposed Findings of Fact and Conclusions of Law [ECF No. 1102] ¶ 86 ("Charles and Dee did not file gift tax returns in the years the IRS alleges that they made gifts.”); IRS’ Amended Proposed Findings of Facts and Conclusions of Law [ECF No. 1103] ¶ 567 ("Charles and Dee Wyly did not file gift tax • returns for gifts made in tax years ... 2010.").
. See Enayat v. C.I.R.,
. IRS’ Amended Proposed Findings of Facts and Conclusions of Law [ECF No. 1103] ¶ 239.
. Id.
. Computation Stipulations ¶ 18.
. 26 U.S.C. § 6038.
. Id. § 6038(a).
. Id. §§ 6038, 6048; 26 C.F.R. § 1.6038-2(a).
. 26 U.S.C. § 6038(b).
. Id. § 6048.
. Id. § 6048(a)(1), (a)(3)(A)(i).
. Id. § 6048(a)(1), (a)(3)(A)(ii).
. Id. § 6048(c)(1).
. Id.; 26 C.F.R. §§ 16.3-1,404.6048-1.
. 26 U.S.C. § 6677(a), The Court notes that the $10,000 alternative minimum penalty is only effective for notices and returns required to be filed after December 31, 2009. Hiring Incentives to Restore Employment Act, Pub.L. No. 111-147, § 535, 124 Stat. 71 (2010). However, since the $10,000 alternative minimum penalty is not applicable to any of the failures to file forms at issue in these Cases, this fact does not affect the Court’s analysis.
. Id. § 6048(b).
. Id. § 6048(b)(1).
. Id. § 6048(b); 26 C.F.R. §§ 16.3-1, 404.6048-1.
. 26 U.S.C. § 6677(b). Again, the Court notes that the $10,000 alternative minimum penalty is only effective for notices and re
. Id.
. Collateral Estoppel Nos. 53, 54,
. When the Court references the Foreign Corporations as to Dee, it is only referring to those of the Foreign Corporations owned by the Charles and Dee International Penalty Trusts. Similarly, when the Court references the Foreign Corporations as to Sam, it is only referring to those of the Foreign Corporations owned by the Sam International Penalty Trusts.
. 26 U.S.C. § 6038(a).
. See Computation Stipulations ¶¶ 9.A-9.E and 22.A-22.E.
.26 U.S.C. § 6038(e)(2). 26 C.F.R. § 1.6038-2(b) in turn defines ''control” for the purposes of 26 U.S.C. § 6038 and Form 5471 in the following way:
A person shall be deemed to be in control of a foreign coiporation if at any time during that person’s taxable year it owns stock possessing more than 50 percent of the total combined voting power of all classes of stock entitled to vote, or more than 50 percent of the total value of shares of all classes of stock of the foreign corporation. A person in control of a corporation which, in turn, owns more than 50 percent of the combined voting power, or of the value, of all classes of stock of another corporation is also treated as being in control of such other corporation. The provisions of this paragraph may be illustrated by the following example:
Example. Corporation A owns 51 percent of the voting stock in Corporation B. Corporation B owns 51 percent of the voting stock in Corporation C. Corporation C in turn owns 51 percent of the voting stock in Corporation D. Corporation D is controlled by Corporation A.
. 26 U.S.C. § 318(a)(2)(B)(ii),
. See id. §§ 671-679; Collateral Estoppel Nos. 53, 54.
. 26 U.S.C. § 318(a)(l)(A)(i).
. Id. § 318(a)(2)(A).
. Id. § 318(a)(2)(B)(i).
. Id. § 318(a)(2)(B)(ii).
. Tex. Fam. Code Ann. § 3.003 (providing that, under Texas law, "[p]roperty possessed by either spouse during or on dissolution of marriage is presumed to be communily property” and that "[t]he degree of proof necessary to establish that property is separate property is clear and convincing evidence”).
. Tr. Trans. 3484:19-3485:9, 3489:15-17. During these transcript excerpts, the Court and the parties are discussing a list of joint questions that the Court provided to the Debtors and the IRS in writing in advance of closing arguments in hopes of getting detailed answers to the Court's questions during closing arguments.
. This question .was also from the list that the Court provided to the parties in advance of closing arguments. It reads as follows:
15. The parties’ briefing on Contested Issue of Law D is thin, why wouldn’t the grantor trust determination of the SDNY Court continue to apply after 2004 unless there were material factual or legal changes relating to the IOM Trusts?
a. Debtors need to help me understand their argument here. No cases cited by either party, but IRS argument makes sense to me.
b. If I’m overlooking briefing, where is it more fully briefed?
. Joint Pre-Trial Order [ECF No. 1014] at 36.
. Tr. Trans. 3485:2-9.
. This question was also from the list that the Court provided to the parties in advance of closing arguments.
. Joint Pre-Trial Order [ECF No. 1014] ait 39.
. Tr. Trans, at 3489:15-17,
. Ergo Science, Inc. v. Martin,
. See 26 U.S.C. § 6038(b):
(b) Dollar penalty for failure to furnish information.—
(1) In general.—If any person fails to furnish, within the time prescribed under paragraph (2) of subsection (a), any information with respect to any foreign business entity required under paragraph (l)of subsection (a), such person shall pay a penalty of $10,000 for each annual accounting period with respect to which such failure exists.
(2) Increase in penalty where failure continues after notification.—If any failure described in paragraph (1) continues for more than 90 days after the day on which the Secretary mails notice of such failure to the United States person, such person shall pay a penalty (in addition to the amount required under paragraph (1)) of $10,000 for each 30-day (or fraction thereof) during which such failure continues with respect to any annual accounting period after the expiration of such 90-day period. The increase in any penalty under this paragraph shall not exceed $50,000.
The Computation Stipulations break down the exact amount of penalties for which Sam and Dee respectively will be liable if this Court does not grant relief due to reasonable cause or under the Eighth Amendment. Computation Stipulations ¶¶ 10 and 23,
. 26 U.S.C. § 6048(b).
. See Computation Stipulations ¶¶ 7.A-8 and 20.A-21 (breaking down the trusts for which Forms.3520-A should have been tiled and the total amount of applicable penalties).
. See 26 U.S.C. §§ 6038(b), 6677.
. See Computation Stipulations ¶¶ 8 and 21 (indicating amounts much greater than $10,000 for each year at issue).
. 26 U.S.C. § 6048(c)(1).
. DISTRIBUTION, Black’s Law Dictionary (10th ed.2014).
.IRS Notice 97-34, Information Reporting on Transactions with Foreign Trusts and on Large Foreign Gifts,
. IRS Post-Trial Brief [ECF No. 1118] at 30. Note that because of the operation of community property laws, any distributions received by either Charles or Dee are treated as received by both Charles and Dee. See Tex. Const, art. 16, § 15; Tex. Fam. Code Ann. §§ 3.001-3.003.
. See Computation Stipulations ¶¶ 12.B and 25.B (listing annuity income for which the IRS believes that Forms 3520 should have been filed).
. See 26 U.S.C. § 6048(c); see also IRS Notice 97-34 at *14 (distinguishing gratuitous distributions from compensation or certain transfers otherwise taxable).
.As was the case in their gift analysis, the IRS merges and melds these doctrines in their post-trial briefing. See IRS Post-Trial Brief [ECF No. 1118] at 38-42. Although the heading of the portion of the IRS’ post-trial brief covering these issues discusses only what "the substance of the transactions, rather than their form" demands, the brief also discusses the economic substance doctrine and the step transaction doctrine.
. Debtors’ Post-Trial Brief [ECF No. 1117] at 58.
. 26 U.S.C. § 6048(c).
. See id. § 6048(c)(1) (emphasis added).
. U.S. V. Kaluza,
. Carrieri v. Jobs.com Inc.,
. Lamie v. U.S. Trustee,
. U.S. v. Transocean Deepwater Drilling, Inc.,
. Id.
. Elgin Nursing and Rehab. Center v. U.S. Dept. of Health and Human Services,
. Flora v. U.S.,
. 26 U.S.C. § 6048(c).
. Id. at § 6048(c) (emphasis added).
. Carrieri,
.2A Sutherland Statutory Construction § 47:33 (7th ed.) (internal marks omitted).
. Barnhart v. Thomas,
. Id. at 28,
. D.G. ex rel. LaNisha T. v. New Caney Indep. School Dist.,
. U.S. v. Campbell,
. Gould v. Gould,
. C.I.R. v. Acker,
.Stephan v. C.I.R.,
. U.S. v. Marshall,
. Rand,
. Debtors’ Post-Trial Brief [ECF No. 1117] at 59.
. 26 C.F.R. § 1.679-4(c) (discussing when certain obligations can be ignored for the purposes of § 679).
. Although, as explained in at pp. 566-67 n. 1237, infra, the Court finds that the IRS is estopped from arguing that the annuity payments were gratuitous transfers based upon its agreements in the Computation Stipulations, the Court will nonetheless consider this argument.
. Id. at § 1.679-4(c).
. 26 U.S.C.§ 679(a)(1); 26 C.F.R. §§ 1.679-1, 1.679-4,
. 26 C.F.R. § 1.679-4(b); see 26 U.S.C. § 679(a)(2).
. 26 C.F.R. § 1.679-4(c); see 26 U.S.C. § 679(a)(3).
. In support of its argument that the private annuity payments should be treated as gratuitous transfers rather than fair market value exchanges for the purpose of § 6048(c), the IRS also points to language in IRS Notice 97-34 that defines a distribution as “any gratuitous transfer of money or property from a foreign trust." However, the IRS cites no statutory or regulatory authority that indicates that annuity payments can be construed as gratuitous transfers. See IRS Post-Trial Brief [ECF No. 1118] at 37.
. Computations Stipulations ¶¶ 1-2 (Sam income tax and penalty liability), 3-6 (Sam gift tax and penalty liability), 7.A-12.B (Sam International Penalties liability), 13-14 (Dee income tax and penalty liability), 15-19 (Dee gift tax and penalty liability), 20.A-25.B (Dee International Penalties liability). The Computation Stipulations are subject to certain contingencies. See id. ¶¶ 26-32.
. See id. ¶ 32.
. See id. ¶¶ 1, 13.
. Id. ¶¶ 1, 13; Proof of Claim (Sam) at note 1(b); Proof of Claim (Dee) at note 1(b).
. See 26 U.S.C. § 952(a) (“For purposes of this subpart, the term 'subpart F income' means, in the case of any controlled foreign corporation, the sum of... ”),
. Proof of Claim (Sam) at note 1(b); Proof of Claim (Dee) at note 1(b).
. Debtors’ Reply to IRS’ Post-Trial Brief [ECF No. 1121] at 67-68.
. Id. at 70 ("[T]he Debtors are not certain of the IRS’ current position as to that agreement given its request that this Court find for it on both its gift tax argument and its Form 3520 reporting argument without disclosing the contradictory nature of those positions.”).
. Markow v. Alcock,
.
. Id. at 599-600.
. See Computation Stipulations ¶ 40 (noting a date of January 26, 2016).
. Id. ¶ 32.
. Tr. Trans. 3461:1-6 (Adams).
. For the same reasons, the Court also concludes that the IRS is estopped from arguing that the annuity payments were gratuitous transfers. During closing arguments, the Court asked Debtors' counsel what the consequences would be if the Court found that the annuity transactions were flawed, and specifically whether this would allow the annuity
. Klamath,
. Security Indus. Ins. Co.,
. Southgate Master Fund, L.L.C.,
. Chemtech Royalty Assoc., L.P., v. U.S.,
. Gregory v. Helvering,
. Acker,
. See Debtors’ Post-Trial Brief [ECF No. 1117] at 60.
. See, e.g., Tr. Trans. 1592:22-1593:4 (IRS Agent Herrick testifying that the Wylys’ manner of reporting annuity income was "unusual”).
. See, e.g., id. 1914:4-1915:14 (Henning-ton testifying that there was no way in their tax program to make sure that additional self-employment tax was added in without reporting the income on Schedule C, and that Pul-man and French advised the Wylys that the annuity payments were subject to self-employment tax), 2210:5-19 (Hennington, however, later testified that she could override the system, but only does so "if it is absolutely necessary.”).
.IRS’ Amended Proposed Findings of Facts and Conclusions of Law [ECF 1103] ¶118. The IRS has also stated that ”[b]e-cause the maximum amount of taxable earnings subject to the self-employment tax went from a maximum of $87,000 in 2003 to a maximum of $113,700 in 2013, none of the annuity income reported on the Schedules C to their income tax returns increased the amount of the Wylys’ self-employment tax since they earned more than the maximum subject to the tax from other sources of income properly listed on the Schedules C. All annuity income reported on the Schedule C, however, would have been subject to the 2.9% hospital insurance (HI) tax.” Id. ¶ 119.
. See, e.g., Joint Ex. Ill (Sam 2007 tax return) at SWYLY 023031; Tr. Trans. 1596:10-1598:23 (Herrick describing how the reporting of the annuity payments simply as "ANNUITIES” was how they were reported on Wyly 1040s).
. IRS' Amended Proposed Findings of Facts and Conclusions of Law [ECF No. 1103] ¶¶ 418-21; IRS Post-Trial Brief [ECF No. 1118] at 68-79.
. IRS’ Amended Proposed Findings of Facts and Conclusions of Law [ECF No. 1103] ¶¶ 430-33; IRS Post-Trial Brief [ECF No. 1118] at 61-68.
. Debtors' Post-Trial Brief [ECF No. 1117] at 61.
. IRS Post-Trial Brief [ECF No. 1118] at 59-61; see also Computation Stipulations ¶¶ 12.B; 25.B.
. See IRS Post-Trial Brief [ECF No. 1118] at 59; Joint Stipulations ¶¶ 297, 299.
. Joint Stipulations ¶¶ 87, 297.
. Collateral Estoppel Nos. 21-24.
. See IRS Post-Trial Brief [ECF No. 1118] at 60; Joint Stipulations ¶ 301.
. Joint Stipulations ¶ 301.
. Id. ¶ 36.
. Collateral Estoppel Nos. 21-24.
. Joint Stipulations ¶¶ 293, 294; Debtors’ Ex. B.
. Joint Stipulations ¶ 27.
. Collateral Estoppel Nos. 17, 47-54.
. See IRS Post-Trial Brief [ECF No. 1118] at 60; Joint Stipulations ¶¶ 287, 288.
. Joint Stipulations ¶¶ 287, 288.
. id. ¶ 21.
. See IRS Post-Trial Brief [ECF No. 1118] at 60; Joint Stipulations $ 289.
. Joint Stipulations ¶¶ 21, 289.
. See IRS Post-Trial Brief [ECF No. 1118] at 60; Joint Stipulations $ 290.-
. Joint Stipulations ¶¶ 21, 289.
. See IRS Post-Trial Brief [ECF No. 1118] at 61; Joint Stipulations ¶ 292 ("In June 2001, East Baton Rouge Limited (IOM), East Carroll Limited (IOM), Moberly Limited (IOM), and Yurta Faf Limited (IOM), transferred a number of financial assets to Greenbriar Limited (IOM), which in turn, loaned the assets it received, together with additional financial assets of its own to Security Capital in return for a promissory note from Security Capital to pay Greenbriar Limited (IOM) $55,815,672.03.”). Security Capi
. Joint Stipulations ¶ 21.
. IdA 36.
. See IRS Post-Trial Brief [ECF No. 1118] at 60; Joint Stipulations $ 295.
. Joint Stipulations ¶¶ 21, 295.
. See IRS Post-Trial Brief [ECF No. 1118] at 59-60; Joint Stipulations $ 21; Collateral Estoppel No. 54.
. See 26 U.S.C. § 6048(c).
. See IRS Notice 97-34, at *14-15.
. 26 C.F.R. § 1.641(a)-0.
. See Federal Tax Coordinator 2d (RIA), ¶ C-1002, Taxation of Grantor Trusts, 19xx WL 218101 (2016) ("To the extent that the grantor trust rules apply, the regular rules for taxing trusts and their beneficiaries ... do not apply.”).
. 26 U.S.C. § 643(i).
. Reprising an argument that it made in the context of the annuity payments, the IRS also argues that the loans should be treated as gratuitous transfers rather than loans under the principles of 26 U.S.C. § 679 and 26 C.F.R. § 1.679-4. This argument was addressed in the context of the annuity transactions, and the analysis is the same here. The statutes and regulations cited by the IRS are not applicable to this situation. See pp. 563-64, supra.
. See Wyly Exs. B(Sam), D (Charles), E (Charles), (F) Sam).
. Sam’s January 2002 loan from Security Capital is factually different from his other loans from Security Capital in one potentially material respect — i.e, Sam was unable to repay the loan at maturity and Security Capital and he agreed to restructure the loan on favorable terms. However, Sam reduced the principal amount outstanding on this loan by $1,500,000 and paid an overdue annual interest payment to Security Capital in order to obtain an extension of the original maturity date to July 14, 2018. From this Court’s perspective, this difference does not make the loan a gratuitous transfer.
. Wyly Ex. D.
. Id. at SWYLY053519.
. Tr. Trans. 2089:1-6 (Hennington).
. Wyly Ex. E.
. Id. at SWYLY053511.
. Id.
. Tr. Trans. 2089:1-6 (Hennington).
. See Case No. 14-35074, Claim Nos. 6-1, 7-1. Security Capital seeks to collect $6,000,000 in principal and $598,610.96 in pre-petition interest related to Charles’ October 2002 loan, along with additional interest, attorney fees, and costs. Security Capital also seeks to collect $25,000,000 in principal and $5,503,561.64 in pre-petition interest related to Charles’ March 2003 loan, along with additional interest, attorney fees, and costs.
. Wyly Ex. F.
. Id. at SWYLY053503.
. Tr. Trans, 2088:13-25 (Hennington).
. See Case No. 14-35043, Claim No. 12-1. The Security Capital Proof of Claim seeks $10,089,149.33 plus costs, attorney fees, and additional interest related to this loan. $10,000,000 of the Proof of Claim represents the unpaid principal of the $10,000,000 July 2003 loan, and $89,149.33 represents pre-petition interest.
. Wyly Ex. B.
. Id.
. Id.
. Id. at 17-18.
. See Wyly Exs. D, E, and F (promissory notes); Joint Stipulations ¶¶ 285-302.
. See pp. 570-71, supra.
. See Wyly Post-Trial Brief at 63; Joint Stipulations ¶¶ 27, 36, 87, 297, 292, 293, 297, 299, and 301 (charting the paths of the loans at issue that were received by the Wylys).
. 26 U.S.C. § 6048(a).
. Joint Stipulations ¶¶ 168 and 169.
. Id. at ¶¶ 19, 21, 25 27, 78, 80, 88, and 94; Collateral Estoppel Nos. 21-24.
. IRS Post-Trial Brief [ECF No. 1118] at 79-80.
. Joint Stipulations ¶¶ 168 and 169.
. See pp. 559-61, supra.
.26 U.S.C. § 6038(a)(2) (Secretary determines when Form 5471 is due); 26 C.F.R. § 1.6038-2(i) ("Returns on Form 5471 required under paragraph (a) of this section shall be filed with the United States person’s income tax return on or before the date required by law for the filing of that person's income tax return. Directors of Field Operations and Field Directors are authorized to grant reasonable extensions of time for filing returns on Form 5471 in accordance with the applicable provisions of § 1.6081-1 of this chapter. An application for an extension of time for filing a return of income shall also be considered as an application for an extension of time for filing returns on Form 5471,”).
. See Computation Stipulations ¶¶ 9.A-10, 22.A-23.
. 26 U.S.C. § 6038(c)(4)(B). This reasonable cause provision operates to relieve taxpayers from liability under § 6038(b) as well as under § 6038(c)(1), which penalizes taxpayers for violations of § 6038(a) by reducing their foreign tax credits; however, § 6038(c)(1) is not at issue here. In addition, § 6038(c)(4)(B) also operates to extend the 90-day period relevant for post-notification penalties under § 6038(b)(2).
. See id. § 6048(b)(1).
. 2015 Instructions for Form 3520-A.
. 26 U.S.C. § 6677.
. See. Computation Stipulations ¶¶ 7.A-8, 20.A-21.
. 26 U.S.C. § 6677(d). The fact that a foreign jurisdiction would impose a civil or criminal penalty on the taxpayer (or any other person) for disclosing the required information is not reasonable cause. 26 U.S.C. § 6677(d).
. Brinkley,
. Klamath, 568 F,3d at 548 (citing Montgomery,
. Brinkley,
. Streber,
. 26 C.F.R. § 1.6664-4(b).
.
. Staff IT, Inc.,
. Boyle,
. Staff IT, Inc.,
. James v. U.S.,
. See pp. 475-513, supra.
. See Boyle,
. Whitehouse Hotel Ltd. P’ship,
. Brinkley,
. Brinkley,
. Southgate Master Fund, L.L.C.,
. Id.
. Thomas,
. See Debtors' Pre-Trial Brief [ECF No. 1015] at 62-74, 106-07.
. See id. at 62-74.
.
. Rice v. C.I.R.,
.
. Debtors' Amended Proposed Findings of Facts and Conclusions of Law [ECF No. 1102] at 206-07.
. The evidence shows that Dee relied entirely on Charles regarding all business, tax, and legal matters throughout their marriage. Tr. Trans. 159:20-160:15 (Dee testified that she relied entirely on husband throughout marriage), 159:13-19(Dee) ("Q. Have you ever prepared a tax return? A. Oh, heavens no.”), 172:17-19 (Dee never discussed tax matters with husband), 1073:14-1075:2 (Sam testifying that he has not read a legal opinion), 387:10-388:11 (Sam testifying how he came to rely on tax professionals and that he did not understand the tax laws and regulations). Tr. Trans. 1074:18-1075:2 (Sam testifying that he did not personally read the opinion letter at IRS Ex. 177 addressed to him).
. Tr. Trans. 159:13-160:15, 293:2-294:23 (Dee testifying that she relied entirely on Charles to handle all tax and legal matters throughout their marriage, and it was her practice to simply sign whatever tax return was put in front of her without reviewing it), 389:25-390:17 (Sam testifying that he has not prepared his own tax returns or the underlying figures for his tax returns since the 1960s), 400:16-401:18 (Sam testifying that he relied on accountants and tax lawyers to prepare his tax returns because “Well, they had experience in doing it. They knew how to do it. They had dealt with it, and it’s not something I had personally done ... And — and I had a lot of other things to do.”), 414:9-25, 703:4-25 (in describing his management style, Sam testified that "I did what I learned. I — I needed to get real good people who knew how to do whatever it is that they did in all kinds of areas, whether they were technology or accounting or law or what have you. And I needed to let these people do what they do, because everybody knew more about anything than I would personally know”), 709:1-20 (Sam testified that he delegated the specifics of the offshore system to French and that "I didn’t confer with Michael French on every specific of how he and other lawyers were
. Yelencsics v. C.I.R.,
. See, e.g, Barter Systems, Inc. of Wichita v. C.I.R.,
.Carlins v. C.I.R.,
. See, e.g., Bruce v. C.I.R.,
. See Debtors’ Pre-Trial Brief [ECF No. 1015] 151-54, 165 (emphasis added).
. See id. ¶ 157 (citing Boyle,
. See id. ¶ 159.
. See id. ¶ 151.
. See id. ¶ 167.
. According to the IRS, neither Sam nor Evan could state a single fact that Meadows Owens relied on in giving the advice. IRS Post-Trial Brief at 17 (citing Tr. Trans. 1703:15-23(Sam); 1851-1853(Evan)).
. IRS Post-Trial Reply Brief [EOF No. 1120] at 10-11 (footnotes omitted).
. See Computation Stipulations ¶¶ 9.A-10, 22.A-23.
. Chatzky said that he believed such an opinion was issued, but no such opinion was admitted into evidence. Tr. Trans. 1170:1-11 (Chatzky). In fact, while Debtors’ counsel attempted to refresh Chatzky’s recollection using a draft opinion letter dated February 2, 1992, that draft is unsigned and was not offered into evidence. Accordingly, there is no evidence in the record as to whether an opinion regarding the Bulldog IOM Trust was ever finalized, signed and issued to Sam. It goes without saying, therefore, that we have no idea on this record what such an opinion, if ever finalized, signed and issued would have said.
. SEC Tr.' Trans. 3738:11-3738:14 (French).
.Chatzky testified that he worked with Tedder's firm from time to time on particular clients, but that at some point in time they became partners in the same firm. While Chatzky could not be precise as to the timing, it was sometime between the April 1992 opinion letters just discussed and the May 19, 1993 opinion letters. Tr. Trans. 1134:121136:24 (Chatzky). Moreover, by February 22, 1996, Tedder and Chatzky were no longer law partners because Tedder "had a penchant for making statements to people that were either questionable or flatly un-true_” Id. at 1137:15-17. According to Chatzky, this made him uncomfortable, so the firm dissolved and Chatzky returned to practicing through his own firm, Chatzky & Associates. Id. at 1138:18-1139:9. After the dissolution of their firm, Chatzky testified that he no longer worked on common clients with Tedder, id. at 1139:16-20, and has never seen him, id. at 11411-5.
. See pp. 500-01, supra.
. See pp. 371-74, 413-16, supra.
. See id.
. See pp. 413-16, supra.
. See id.
. See pp. 415-23, 494-98, supra.
. See pp. 494-98, supra.
. See pp. 415-23, supra.
. See pp. 475-513, supra.
.See pp. 491-93, supra.
.. See pp. 371-74, 491-93, supra.
. See id. In fact, Meadows Owens did not opine on the proper legal characterization of the Sam International Penalty Trusts at that time either. Rather, they simply concluded that the Wylys had a "reportable position” for tax purposes.
. See Debtors' Pre-Trial Brief [ECF No. 1015] ¶[¶ 151-54, 165.
. That this was in fact the nature of the implicit advice given is supported by the fact that Sam’s advisors did have him file Forms 3520 and 3520-A for foreign trusts that they did believe Sam was the grantor of. See Joint Exs. 142-175.
. See Nance v. U.S.,
. See Debtors’ Pre-Trial Brief [ECF No. 1015] ¶¶ 151-54, 165; Joint Exs. 142-175.
. Wyly Ex. LN. This memorandum is addressing the Red Mountain IOM Trust, a trust settled by Cairns in 1995. But this trust is identical to the La Fourche IOM Trust settled by Cairns in 1995 on Sam's behalf. See IRS Exs. 17 (Deed of Settlement, La Fourche IOM Trust) and 42 (Deed of Settlement, Red Mountain IOM Trust).
. Wyly Ex. OC at WYLYSEC01105085.
. IRS Ex. 85.
. Id. at SECI00150285.
. Boyle,
. See, e.g., IRS Ex. 85 at SECI00150263 (Robertson’s 1991 notes on a Tedder seminar describing an annuity transaction involving a foreign corporation, “Problems: $1,000,000,000 funds is going into annuities annually. The IRS will address soon, if you wish tax advantage of this loophole do now. Tedder considers this the best estate planning tool. This is an aggressive tax mode to take— be sure to file every tax form available and any support schedule that seems pertinent.’’); Tr. Trans. 1038:19-1044:4 (On cross examination, Sam admitted that he received these notes in 1991 and was on notice that the structures Tedder proposed were aggressive).
.See, e.g., IRS Ex. 85 at SECI00150263 (Robertson’s 1991 notes on a Tedder seminar stating “Always over disclose what you’ve done to the IRS ... Always show your chart to the creditor, rely on law not secrecy.”), SECI00150266 (Robertson’s notes on a 1991 Tedder seminar examining a real estate transaction and private annuity structure similar to that used by the Wylys and stating "Tedder
. See pp. 371-73, 413-16, supra.
. See pp. 415-23, supra.
. Tr. Trans. 387:10-388:11 (Sam testifying how he came to rely on tax professionals and that he did not understand the tax laws and regulations), 389:25-390:17 (Sam testifying that he has not prepared his own tax returns or the underlying figures for his tax returns since the 1960s), 400:16-401:18 (Sam testifying that he relied on accountants and tax lawyers to prepare his tax returns because "Well, they had experience in doing it. They knew how to do it. They had dealt with it, and it’s not something I had personally done ... And — and I had a lot of other things to do.”), 414:9-25, 703:4-25 (in describing his management style, Sam testified that "I did what I learned. I — I needed to get real good people who knew how to do whatever it is that they did in all kinds of areas, whether they were technology or accounting or law or what have you. And I needed to let these people do what they do, because everybody knew more about anything than I would personally know”), 709:1-20 (Sam testified that he delegated the specifics of the offshore system to French and that "I didn’t confer with Michael French on every specific of how he and other lawyers were setting up trusts and doing the legal things that they did."), 722:13-725:2 (Sam, describing the process that went into preparing his tax returns from 1992 through 2013, and testifying that he did not carefully read his 1992 tax return because "I can’t say 1 was competent to read it” and that he signed it because "it was prepared by people that knew what they were doing. They were professional people, accountants, and they were lawyers.”).
.Based on the testimony provided at trial, the Court has questions about characterizing Tedder as a tax expert, but the Court is satisfied that Chatzky is a knowledgeable tax lawyer and that Lubar is an exceptionally well credentialed and knowledgeable tax lawyer.
.IRS Ex. 96 (memorandum dated June 30, 2003 from Hennington and Boucher to, among others, Sam and Charles discussing concerns); Tr. Trans, 1924:24-1925:16 (Hen-nington testified that she learned about Lubar and his connection with the Wyly family when she "received a — a call from Michelle Boucher relating to me that she had run into Mr. Lubar at a conference in the Cayman Islands, and that Mr. Lubar had made a comment to her that he thought there were issues with the '92 trusts and that he had told Mike that back years ago, and basically that she needed to look into it.”)
. Tr. Trans. 1924:24-1951:24 (Hennington described the investigations that were done in response to Lubar's concerns): IRS Ex. 96 (a memo reporting to Sam, Charles, Evan, and Donnie what Hennington and Boucher had learned from investigating Lubar's concerns regarding the offshore system).
. IRS Ex. 96.
.See Wyly Exs. OC at WYLY-SEC01105084-85 (outline of meeting of Hen-nington, Pulman, and other Meadows Owens lawyers that, among other things, explained that “Todd Welty went through the penalties associated with not filing a 3520 and 5471. He went on to say that the disclosure would alleviate some of the accuracy-related penalties under § 6662, but if the transaction was a tax shelter, the disclosure would not alleviate potential penalties. Todd Welty stated the biggest penalty risk is under § 6677, which provides a for a penalty of 5% of the gross asset of the trust at the end of the year.”), OD (similar outline of a meeting that Cousins held . with Sam and Evan on October 15, ■ 2003 outlining potential penalties for failures to file Forms 3520-A and 5471); Tr. Trans. 1787:9-18 (Cousins) (identifying Wyly Ex. OD as his meeting outline for a meeting he held with Sam and Evan).
. Wyly Ex. OB.
. Id. at WYLYSEC01112419-2420. The meeting notes refer to Form “3528,” which the Court believes is actually a reference to Form 3520-A.
. See pp. 458-60, supra.
. 26 U.S.C. §§ 6038, 6048.
. See Joint Exs. 110 (Sam 2006), 111 (Sam 2007), 112 (Sam 2008), 130 (Dee and Charles 2003), 133 (Dee and Charles 2006), 134 (Dee and Charles 2007), 135 (Dee and Charles 2008), IRS Exs. 40 (Dee and Charles ‘2004), 42 (Dee and Charles 2005), 50 (Dee and Charles 2009), 52 (Dee and Charles 2010), 54 (Dee and Charles 2011), 71 (Sam 2002) 74 (Sam 2004), 75 (Sam 2005), 155 (Sam 2003), 159 (Sam 2009), 160 (Sam 2010), 161 (Sam 2011), 162 (Sam 2012), 163 (Sam 2013).
. 26 U.S.C. §§ 6038, 6048.
. Tr. Trans. 2072:17-2074:13 (Henning-ton) ("[The IRS] made clear that [the foreign trusts and annuities] was the focus of their audit when they started in ’04.” Hennington also testified that the IRS’ audit of Sam and Charles began sometime in "Early 2004,” after Sam filed his first Form 8275 disclosure).
. As we know, Sam had been audited before and had been the subject of prior tax court decisions. See Joint Exs. 188 (tax court decision related to Sam for 1998), 189 (tax court decision related to Sam for 1999); Tr. Trans. 2448:6-2462:16 (Hennington describing previous audits involving Sam and Wyly-related entities Computer Associates and Green Funding Corporation).
. See Debtors' Amended Proposed Findings of Facts and Conclusions of Law [ECF No. 1102] ¶ 371, The IRS is more blunt in its characterization: "Caroline Wyly did not raise a reasonable cause defense; rather; [sic] her only defense to the penalties in this case is that she didn’t know about, and relied
.26 C.F.R. § 1.6664-4(c)(2).
.
. Reser,
. Id. at*l.
. Id.
. Id.
. Id. at *3.
. Id. at *4.
. Id.
. Id.
. Id. at *6.
. Id. at *8.
. Id.
. Id.
. Id. at *9.
. Id. at *10 (internal citations omitted).
. Reser,
. Id.
. Id.
. Id. at 1262.
. Id. at 1268.
. Id.
. -Id.
. Id.
. Id.
. Id. at 1270.
. Id. at 1271.
. Id. at 1271-72.
. Id. at 1272.
. Id.
. See pp. 464-76, supra.
. Tr. Trans. 159:20-160:15(Dee) (relied entirely on husband throughout marriage).
. Id. at 159:13-19(Dee) ("Q. Have you ever prepared a tax return? A. Oh, heavens no.”); 172:17-19 (Dee never discussed tax matters with husband).
. Id. at 159:13-160:9, 293:2-294:23(Dee).
. Id. at 1336:17-1338:12 (Donnie Miller) ("Q. And did you ever discuss the offshore trust system with Dee Wyly? A, No, I didn’t. Q. Did you ever hear Charles Wyly talk business with Dee? A. No. Q. Did you ever hear anyone talk about business with Dee Wyly? A. No. Q. In the 34 years, thereabouts, that you’ve known Dee Wyly, have you ever talked business with her? A. No. Q. To your knowledge, did anyone inform Dee Wyly about the intricacies of the offshore trust system? A. Not to my knowledge, no.”), 164:5-165:3(Dee) (first heard the name Soulieana at her deposition in July 2015, never discussed IOM structure with anyone before bankruptcy case filed), 165:22-166:23; 174:16-24(Dee) (didn’t ever see Eiseman or Marguerite Green invoices at the time purchases were made), 182:10-183:3; 183:18-20(Dee) (never heard of Tyler IOM Trust or Keith King), 184:20-185:11, 186:12-15(Dee) (never heard of Red Mountain IOM Trust or Shaun Cairns), 322:6-14(Dee) (does not know what a limited
.Id. at 164:5-165:3(Dee); 322:13-14(Dee).
. Id. at 151:8-24(Dee).
. Reser,
. See p. 446 n. 573, supra.
. Reser,
. Tr. Trans. 3027:14-16 (Dubinsky).
. Reser,
. See 26 U.S.C. § 6013.
. See id. §§ 6013, 6038, 6048, 6677.
. Tr. Trans. 160:10-161:14(Dee).
.Belk v. C.I.R.,
.
. Id. at *5.
. See, e.g., id.
. Boyle,
. U.S. Const, amend. VIII.
. U.S. v. Bajakajian,
. These four cases are U.S. v. Halper,
. IRS Post-Trial Brief [ECF No. 1118] at 95.
. U.S. v. Halper,
. See Bajakajian,
. Halper,
. Id.
. Id.
. Id.
. U.S. Const, amend. V.
. Halper,
. Id. at 448-49,
. Id.
. Id. at 448,
. Hudson v. U.S.,
. Halper,
. Id. at 451,
. Id. at 446,
. Id. at 449,
.
. Id. at 280,
. Id. at 265,
.
. Id. at 609-10, 622,
. Id. at 609-10,
. Id. at 620 n. 12,
. Id. at 621,
. Id. at 621-22,
. Id. at 622 n. 14,
. Id. at 610-11, 622,
.
. Id. at 327,
. Id. at 325,
. Id.
. Id. at 325, 339,
. Id. at 326,
. Id. at 328,
. Id. at 329 n. 4,
. Id. at 333,
. Id. at 334,
. Id. at 336,
. Id.
; Id.
. Id. at 337,
. Bajakajian,
. Id. at 334,
. Austin,
. Id. at 621,
. Bajakajian,
. Id. at 337-40,
. The Debtors cite two district court cases — Callister Nebeker & McCullough v. U.S. and Crawford v. U.S. Dept. of the Treasury—
.The Court does recognize that the Supreme Court has declared a unique and obviously punitive tax to be punishment for the purposes of a double jeopardy analysis. See Dept. of Rev. of Mont. v. Kurth Ranch,
.
. Id. at 434.
. Id.
. Id. at 434-35.
. Id. at 435.
.
. Id. at 401,
. Id.
. Bickham Lincoln-Mercury Inc. v. U.S.,
. John Corp. v. City of Houston,
. Austin,
. Id. at 602,
. JCS-12-96 NO 9 (I.R.S.),
. General Explanation,
. 26 U.S.C. § 6038(b).
. Id, at §§ 6048(b), 6677. Violations of § 6048(a) or (c) — for which this Court has held the Debtors are not liable — result in penalties of $10,000 or 35% of the value of the property involved in the unreported transfer or distribution, whichever is greater. 26 U.S.C. §§ 6048(a), (c), 6677.
. See IRS’ Amended Proposed Findings of Facts and Conclusions of Law [ECF No. 1103] 11270.
. General Explanation,
. Austin,
. U.S. v. Alt,
. Bickham Lincoln-Mercury Inc.,
. Newell Recycling Co., Inc. v. U.S. E.P.A.,
. McNichols,
. Hudson,
. Austin,
. Bajakajian,
. Id. at 336-37.
. Thomas v. C.I.R.,
.
. Halper,
. Id. at 449,
.
. Id. at 486 (quoting 817 N.E. 29th Drive,
.
. Id. at 1309. See Browning-Ferris Indus.,
. Id. at 487; see also U.S. v. George,
. U.S. V. Wallace,
.
. Id. at 210. The Debtors argue in their post-trial reply that an interpretation of the Excessive Fines Clause where a statutory maximum is always constitutionally permissible is one where "the statute would swallow the Constitution.” See Debtors’ Post-Trial Reply Brief [ECF No, 1121] at 80. However, the Debtors’ argument ignores the fact that Austin and Bajakajian were decided in the context of forfeitures, sanctions that are not just different in degree but different in kind
. But see Vanderbilt Mortg. and Fin., Inc. v. Flores,
. Computation Stipulations ¶¶ 7.A through 9. Were the Court to include the Form 3520 penalties for which it has found that Sam is not liable in the first instance, this figure would climb to $590,428,940. Id.
. Bajakajian,
. Id. at 337-40,
. U.S. v. Ahmad,
. Austin,
. Bajakajian,
. 26 U.S.C. § 6677(b).
. This analysis is different for violations of § 6038. Although income from controlled foreign corporations is taxable to the controlled foreign corporation’s owner under 26 U.S.C. § 951, violations of § 6038 result in a flat fine of $10,000 per violation. Although in certain cases this could make penalties under § 6038 more disproportional than penalties under § 6677, the Court notes that this is certainly not the case here. The minimum penalty under § 6677 is $10,000 per violation, and percentage-based penalties apply here because of the extent of the Wyly wealth that was placed offshore and that Debtors did not report on Form 3520-A. See 26 U.S.C. § 6677. Less than 5% of Sam’s or Dee’s liability for International Penalties is for violations of § 6038. See Computation Stipulations ¶¶ 9.A through, 10, 22.a through 23.
. Thomas,
. See, e.g., U.S. v. Wallace,
. See, e.g., Wallace,
. Bajakajian,
. See IRS Exs. 567 (Hennington writes to Alan Stroud, a lawyer at Meadows Owens "I am sure I read this at the time and overlooked or did not pay attention to the 3520 filing requirement. It seems that we would have preferred to not have anything reportable on the note if that was a possibility,”), 570 (email between Hennington and Boucher where Hennington expresses a lot of concern that certain loans may be subject to reporting requirements); SEC Tr. Trans. 1720:14— 1721:6 (French) (Tedder said to Sam that making SEC filing could jeopardize the tax status of the offshore system).
. See IRS Exs. 567, 570.
. See IRS Ex. 412 (French fax noting the need to avoid SEC reporting requirements); IRS Exs. 567 and 570; SEC Tr. Trans. 1720:14-1721:6 (French) (Tedder said to Sam that making SEC filing could jeopardize the tax status of the offshore system); Joint Exs. 142, 175 (Forms 3520 and 3520-A that the Wylys did file gave a false impression of the offshore system, as they did not include forms for the trusts through which most of the offshore transactions flowed, many of these forms were not dated or signed, and were filed on versions of IRS forms that indicated the forms had been filed late).
. General Explanation,
. Bajakajian,
. General Explanation,
. See IRS Exs. 85 (June 12, 1991 memorandum from Robertson to Sam, Charles, Evan, French, and Ethel Ketter, in-house CPA for the Wyly family office, discussing Tedder’s seminar on asset protection and tax deferral) at SECI00150278 (discussing controlled foreign corporations and recommending multiple jurisdictions, including Cayman and IOM, followed by the statement that "Tedder says all tax haven governments are stable at this time”), 111 (Wyly Family Foreign Trust Planning Confidential Conference Outline dated September 7, 2000) at SWYLY009418, § II.C.2 (referring to the 1992 IOM trusts as having "tax haven status”).
. Bajakajian, 524 U.S, at 337-40,
. Bajakajian,
. Debtors’ Post-Trial Reply Brief [ECF No. 1121] at 81. The Court notes an issue with this number. The IRS maintains, without providing its own figure, that the Debtors "conveniently ignore the substantial amounts of interest due on their unpaid income tax liabilities for all of the years during which they use of funds [sic] belonging to the United States.” IRS Post-Trial Reply Brief [ECF No. 1120] at 71.' The Debtors also note in their post-trial reply that their estimate could be revised to be even lower “when the stipulated income figures are worked through the ‘tax return’ software of the IRS for the appropriate years, after the Court renders its decision. Debtors’ Post-Trial Reply Brief [ECF No. 1121] at 81 n.219. Based on its own calculations derived from the Computation Stipulations, the Court calculates Sam’s tax liability for years 1996 through 2013 to exceed $300,000,000. See Computation Stipulations Attachment A. For the purposes of its Excessive Fines Clause analysis, the Court will assume that the Debtors’ figure, which according to the IRS and the Court's own calculations is low, is correct.
.Sam's counsel also argued at closing, without citation to evidence, that these penalties are 1.4 times greater than the stipulated-to income amounts. Tr. Trans. 3630:5-15 (Cole) (“[M]ost of the money at issue here is from these failure to file penalties. They exceed not only the income tax, but the total income that the parties have stipulated to”).
. See pp. 414-15, 488-95, supra,
. See pp. 421-23, 494-98, supra,
. Bajakajian,
. 26 U.S.C. § 6677.
. Id. § 6677(c)(2).
. Id.
. Computation Stipulations ¶¶ 20.A — 21. If the Court included the Form 3520 penalties, for_ which it has found that Dee is not liable, this figure would climb to $341,348,276. Id.
.
. Id.
. Id. at 179.
. Id.
. Id.
. Id.
. Id.
. Id. at 180.
. Id. at 188-189.
. Id. at 179.
. Id. at 189.
. Id. at 191.
. Id. at 188.
. Bajakajian,
. Tr. Trans. 151:8-24 (Dee testifying that she “literally never” discussed business with Charles), 164:5-165:3(Dee), 322:13-14. (Dee testifying that she never discussed the offshore system with any other person).
. Bajakajian,
. General Explanation,
. Tr. Trans. 159:20-160:15 (Dee testifying that she relied entirely on husband throughout marriage).
. Id. at 159:13-19(Dee) ("Q. Have you ever prepared a tax return? A. Oh, heavens no.”), 172:17-19 (Dee testifying that she never discussed tax matters with husband).
. Id. at 159:13-160:9, 293:2-294:23(Dee).
. von Hofe,
. Bajakajian,
. See Petrella v. Metro-Goldwyn-Mayer, Inc., — U.S. -,
.
. Id. at 19.
. Id. at 25.
. 26 U.S.C. § 6501. It is unclear whether § 6501 applies to the IRS’ claims for penalties, Although § 6501 is a limitation on the time period for assessment of "taxes” and not "penalties,” 26 U.S.C. § 6665(a)(2) states that "[a]ny reference in this title to 'tax’ imposed by this title shall be deemed also to refer to the additions to the tax, additional amounts, and the penalties provided by this chapter." 26 U.S.C. § 6663 is a part of the chapter to which § 6665 refers, and could thus be encompassed by the language of § 6501 referring to "taxes.” Despite this reading, under Sage, it is arguable that there is no statute of limitations for collection of fraud penalties, as no statute of limitations appears on the face of § 6663 and the Sage court refused to apply language similar to § 6665 in order to expand the § 6501 statute of limitations. Sage,
. 26 U.S.C. §§ 6501(c)(1), (c)(8).
.
.
.See, e.g., U.S. v. Fernon,
.
.
. Tregre v. C.I.R.,
. Johnson v. Crown Enter., Inc.,
. Debtors’ Pre-Trial Brief [ECF No. 1015] ¶ 188.
. See, e.g., Niedringhaus,
. See pp. 394-407, 446, supra.
. Michigan Exp., Inc. v. U.S.,
. Knapp v. U.S. Dept. of Agriculture,
. Robertson-Dewar v. Holder,
. Knapp,
. Id, at 460; Robertson-Dewar,
. Heckler,
. Fano v. O’Neill,
. Debtors’ Pre-Trial Brief [ECF No. 1015] ■at ¶ 194.
. Marine Shale Processors,
. Fano,
. Robertson-Dewar,
. Debtors' Pre-Trial Brief [ECF No. 1015] ¶ 188.
.Wyly Ex. OB at WYLYSEC01112418 ("All here are with Counsel. We do not have settlement authority. Our Client is the operational side of IRS ... ”), WYLYSEC01112421 ("Don't usually do this much on anonymous basis. At what point will you say who you are? ... Counsel can only do so much as to general resolution. We can give input into how to resolve these cases, more globally for all affected cases.”), WYLYSEC01112422 ("Someone has to say it's okay to settle.”), WYLYSEC01112423 ("Can’t give you any promises”). An IRS Counsel attorney who was at the meeting testified that no IRS client representative attended the meeting. Tr. Trans. 2864:8-10 (Grimm). Furthermore, Lubar testified regarding this meeting that "I think they were prepared to have one more meeting without identifying the clients, but they made it clear that after that, if we really wanted to tiy to settle this, obviously we had to reveal who the clients were, and that was a big step, of course.” Lubar Depo. Trans. 79:18-80:4.
. Wyly Ex. OB at WYLYSEC01112422. Furthermore, one of the IRS Office of the Chief Counsel attorneys to whom this statement is attributed — Grimm — said that "the Office of Chief Counsel never selects an issue champion. It’s the IRS that does, and they don’t always select an issue champion for issues.” Tr. Trans. 2871:7-13 (Grimm). Grimm also specifically testified that ”[n]o one in Chief Counsel has ever had the authority to select or appoint an issue champion” and that an issue champion does not have the authority to enter into a settlement agreement directly with a taxpayer. Id. at 2873:23-2874:3, 2876:11-14 (Grimm).
. Tr. Trans. at 2876:15-18 (Grimm).
. See, e.g., Walsonavich,
. Marine Shale Processors,
. Triplett v. Heckler,
. Tr. Trans. 2871:7-13 (Grimm). Tr. Trans. 2873:23-2874:3, 2876:11-14 (Grimm). Wyly Ex. OB at WYLYSEC01112418 ("All here are with Counsel. We do not have settlement authority. Our Client is the operational side of IRS- "), WYLY-SEC01112421 (“Don’t usually do this much on anonymous basis. At what point will you say who you are? ... Counsel can only do so much as to general resolution. We can give input into how to resolve these cases, more globally for all affected cases.”), WYLY-SEC01112422 ("Someone has to say it’s okay to settle.”), WYLYSEC01112423 ("Can’t give you any promises”). An IRS Counsel attorney who was at the meeting testified that no IRS client representative attended the meeting. Tr. Trans. 2564:8-10 (Grimm). Furthermore, Lubar testified regarding this meeting that “I think they were prepared to have one more meeting without identifying the clients, but they made it clear that after that, if we really wanted to try to settle this, obviously we had to reveal who the clients were, and that was a big step, of course.” Lubar Depo. Trans. 79:18-80:4.
.U.S. v. Marine Shale Processors,
.
. Id. at 435.
. Id.
. Id.
. Id.
. Id. at 442.
. Id. at 441 ("We reject the notion that IRS agents examining Fredericks’ file sometime in 1984 could have discovered a Form 872-A that was signed in 1980 and not known that the taxpayer had been misled as to its existence given that the three subsequently executed Forms 872 were also in Fredericks’ file. It is exactly this combination of written agreements entered into by the IRS and Fred-ericks that prompted the IRS to forego soliciting additional one-year extensions.”).
.Id. at 442 ("Fredericks argues that if he had known the IRS was in possession of the Form 872-A, he would have filed the necessary document (Form 872-T) to terminate the indefinite consent. Relying on the IRS' misrepresentation that the Form 872-A was not in his file, followed by the IRS’ repeated requests for Form 872 agreements, Fredericks concluded that it was unnecessary to terminate a consent agreement which the IRS maintained that it never received. He concluded that the subsequent Forms 872 were the only agreements relevant to his 1977 return. On June 30, 1984, when the last one-
. In fact, Grimm testified that she did not discover the identity of the taxpayers being represented at the anonymous meeting until late 2015. Tr. Trans. 2869:9-2870:4 (Grimm).
. Id. at 2878:13-17 (Grimm),
. Heckler,
. See id. at 61-62,
. Knapp,
. Fredericks,
. Wyly Ex. OB.
. Joint Pre-Trial Order [EOF No. 1014] at 5.Y.
. Valley Ice & Fuel Co., Inc. v. U.S.,
. Coastal Ref. and Mktg., Inc.,
. Clark v. Barnard,
. See Debtors' Pre-Trial Brief [ECF No, 1015] ¶ 179 (arguing suspension is mandated beginning with the 1998 tax year), 179 n.170 ("There is no suspension for the 2011 and later tax years because the IRS Proofs of claim were issued before the suspension period would begin.”).
. As explained by the Code of Federal Regulations, "[t]he suspension period ... begins the day after the close of'the 18-month period (36-month period, in the case of notices provided after November 25, 2007 .,.) beginning on the later of the date on which the return is filed or the due date of the return without regard to extensions. The suspension period ends 21 days after the earlier of the date on which the IRS mails the required notice to the taxpayer's last known address, the date on which the required notice is hand-delivered to the taxpayer, or the date on which the IRS receives an amended return or other signed written document showing an increased tax liability.” 26 C.F.R. § 301.6404-4(a)(4),
.Joint Stipulations ¶¶ 183-196(Sam) and 206-217(Dee).
. Form 5471 is titled "Information Return of U.S. Persons with Respect to Certain Foreign Corporations.”
Í652. 26 U.S.C. § 6404(g)(2)(D).
. Id. § 6404(g)(2)(B), Mandatory suspension does not apply to gift taxes. Id. § 6404(g)(1)(A) (suspending interest for items relating to "a return of tax imposed by subtitle A” — i.e., income taxes); Debtors' Pre-Trial Brief [ECF No. 1015] at ¶ 179 n.168.
.
.
. Rev. Proc. 2005-38,
. The tax court has refused to give deference to this provision of the Revenue Procedure. See Corbalis,
S8.
. “In the case of any assessment of interest on ... any deficiency attributable in whole or in part to any error or delay by an officer or employee of the Internal Revenue Service (acting in his official capacity) in performing a ministerial act ... the Secretary may abate the assessment of all or any part of such interest for any period.” 26 U.S.C. § 6404(e)(1) (1994 ed.).
.
.The parties have also cited to In re Gurley,
.
. 26 C.F.R. § 301.6404-4(b)(2).
. Sata v. U.S.,
. See pp. 389-462, supra.
. See id.
.While most of the Court’s summary of what happened here will only refer to Sam, it applies equally to Charles, whose transactions and activities offshore mirrored Sam’s in every relevant detail. That the Court must determine whether Charles committed tax fraud is clear since the IRS is asserting fraud penalties against Dee from 1992 through 2013, and during most of those years Dee and Charles filed joint tax returns.
. Accordingly, when the Court cites to transcripts in this Memorandum Opinion, it is only referring to the designated portions of the testimony.
. IRS Ex. 806.
. Id. at WYLYSEC00010967 ¶ 1.
. Joint Ex. 4 (The Bessie Trust agreement).
. These annuities involved Yurta Faf Limited (IOM) and Audubon Asset Limited (IOM). Joint Stipulations ¶ 36 (showing both entities are wholly-owned by Bessie IOM Trust), 131, and 141 (describing annuity transactions).
. See, e.g., Joint Stipulations ¶¶ 292 (financial assets transferred from Yurta Faf Limited (IOM) to Greenbriar Limited (IOM), which Greenbriar Limited (IOM) then loaned to Security Capital and that were ultimately used to fund the Cayman LLCs), 357-359, 364-366 (funds related to the Cottonwood Ventures II property).
. Joint Ex. 17 (La Fourche Trust agreement).
. Collateral Estoppel No. 22; Cairn's Depo Tr. 46:22-47:4, 48:5-49:2.
. Collateral Estoppel No. 22; Cairns Depo. Tr. 43:1-14; 46:16-21.
. IRS Ex. 92.
. Ironically, Wychwood Trust Limited was Cairns’ trust company, through which he then collected trust management fees from Sam related to the La Fourche IOM Trust he purportedly settled for Sam "as an entirely gratuitous act.”
. Cairns Depo. Tr. 47:2-4.
. Tr. Trans. 2029:3-9(Sam); Joint Stipulations ¶¶ 66, 67, 102, 103, 114, 116 (showing Lome House Trust as having served as trustee for various Wyly-related trusts, including the Bulldog IOM Trust, Bessie IOM Tmst, Tallu-lah IOM Trust, Pitkin IOM Tmst, Tyler IOM Tmst, and Woody International IOM Tmst).
. Joint Stipulations ¶ 66 (showing Lome House Tmst serving as trastee of the Bessie IOM Tmst from 1994-1998).
. Collateral Estoppel No. 22; Joint Stipulations ¶¶ 66 (showing Cairns’ tmst company, Wychwood Tmst Limited, serving as trastee for Delhi IOM Trust and La Fourche IOM Tmst) and 102 (Red Mountain IOM Trust).