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United States v. Coplan
703 F.3d 46
2d Cir.
2012
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Docket

*1 Smith, David L. Defendant. applying court The district erred Rosenberg requirements Campbell Docket No. 10-583-cr. appellees’ state-law claims.8 Appeals, States Court Second Circuit. III. Argued: Nov. 2011. February court’s We reverse district Decided: Nov. 2012. motion granting plaintiffs’ order the extent it ruling scope on of class to September class certified

expanded Owners, include Unbound February 24, denying 2012 order

and its stay proceedings motion to

Coverall’s for fur-

pending arbitration. We remand opin- with this proceedings

ther consistent

ion, including stay of a issuance pending Owners’ arbitra-

Unbound claims

tion. ordered. No are awarded.

So costs America,

UNITED STATES

Appellee,

v. COPLAN, Nissenbaum,

Robert Martin Shapiro, Vaughn,

Richard Brian Bolton, Defendants-Appel-

Charles

lants, analysis case-spe- applicable appropriateness "The is were here —which it is not— cases Campbell, 407 "fact-dependent.” cific” and suggest pro- we do not failed to that Coverall F.3d at 554. The circumstances of this case minimally to the Un- vide sufficient notice markedly Campbell differ from those Owners. bound Rosenberg. If the described in those test *7 Anderson, Jacobs,

G. Butler, Donna Brown Snow, O’Mara, Cannada, PLLC, Stevens & MS, Ridgeland, for Defendant-Appellant Brian Vaughn. Garber, Firm,

Marc N. The Garber Law P.C., Marietta, GA, for Defendant-Appel- lant Charles Bolton. Dratel,

Joshua L. Dratel, Joshua L. P.C., York, NY, New for amicus curiae New York Council of Defense Lawyers; Laura Birger Grossfield and Rachel B. Kane, LLP, Cooley York, NY, New for amicus curiae National Association of Lawyers; Criminal Defense in support of Defendants-Appellants. Tarlowe, Richard C. Assistant United KEARSE, McLAUGHLIN, Before: (Mark Attorney, Lanpher, States Andrea CABRANES, Judges. Circuit Surratt, Failla,

L. and Katherine Polk As- sistant Attorneys, United States on the Judge KEARSE part dissents brief), Bharara, for Preet United States separate opinion. Attorney for the Southern District of New CABRANES, JOSÉ A. Judge: Circuit York, York, NY, New Appellee United We consider here the fate of part- four States of America. employees ners and of Ernst & Young, (Donald Riordan, Dennis P. Horgan M. (“E Y”), LLP one largest & account- Dubcoff, brief), Gary on the Riordan & ing world, firms in the appeal who their Francisco, CA; Horgan, San Sampsell Ted convictions in connection with the develop- Jones, Law, William Mitchell College of St. ment and defense of “tax five shelters” Paul, MN, for Defendant-Appellant Rob- that were sold or implemented by E & Y ert Coplan. issue, between 1999 and 2001. At among Lewin, Lewin, Nathan (Alyza D. on the things, other scope is the of criminal liabil- brief), Lewin, LLP, Lewin & Washington, ity conspiracy in a to defraud the DC, for Defendant-Appellant Martin Nis- § States under 18 U.S.C. 371 and the suffi- senbaum. ciency of the evidence with respect to the *8 (Marc Shapiro,

Alexandra A.E. E. Is- criminal intent of certain defendants. Darrow, brief), serles and James on the defendants these ac- consolidated LLP, Shapiro, York, Arato & Isserles New attorneys, tions are three tax Robert Co- NY; Morvillo, Abramowitz, Grand, Iason, Nissenbaum, plan, Martin and Richard Bohrer, P.C., York, NY, Anello & New of accountant, Shapiro, one and Brian counsel; for Defendant-Appellant Richard Vaughn, formerly employed by E & Y. A Shapiro. defendant, Bolton, fifth Charles was an Bergman,

Paul B. Law Offices of Paul investment advisor who operat- owned and PC, York, NY; Bergman, B. New Robert ed various asset-management companies.1 Smith, charged party David the sixth defendant appeal. and is not a to this case, fugitive this awas at the time of trial seeking to who were Nissenbaum, worth” individuals Vaughn and Shapiro, Coplan, defendants”) income million from appeal at least the “trial shelter (jointly, $20 en- of conviction separate judgments called the “VI- liability. Originally from tax States District Court (for the United tered Produce Group “Value Ideas PER” of New York Southern District for the Results”), group was Extraordinary 17, Stein, February on Judge), H. (Sidney (for “Strategic Individual renamed “SISG” 2010, jury trial on following a 10-week Nis- Coplan, in 2000. Group”) Solutions Gov- to defraud the charges conspiracy of senbaum, were the Shapiro, Vaughn and evasion, ernment, tax obstruction Group/SISG. of the VIPER core members (“IRS”), and Revenue Service Internal relate to principally of this case The facts ap- the IRS. Bolton statements to false and audit de- design, implementation, en- of conviction judgment from a peals developed of four tax shelters fense April on by the District Court tered (1) Contingent Group/SISG: VIPER single to a following plea guilty his (2) (“CDS”); Currency Op- Swap Deferred charge.2 conspiracy (“CO- Reward Alternatives Bring tions follow, we reverse reasons that For the (“Add-On”); BRA”); Add-On CDS and Shapiro Nissenbaum the convictions Corporation Personal Investment Three, One, Two, and the on Counts (“PICO”) Nissenbaum, Coplan, shelters. Four, of Nissenbaum Count conviction in a also invested personally Coplan affirm the convictions and we shelter, “E & Y 11 known as the fifth tax entirety. We affirm Vaughn in their “Tradehill,” or which was Transaction” sentencing order Bol- the District Court’s Although the marketed to E & Y clients. imprison- to 15 months of principally ton shelters, only the all five tax IRS audited ment, por- and remand the but we vacate subject later to tax Add-On shelter was a fine of imposed judgment tion of the the oth- charges. respect With evasion million. $3 shelters, charged conduct four tax er or mis- alleged relates to false principally BACKGROUND by the defen- leading statements made convictions, underlying the The evidence audits, with the IRS dants connection light “in most favorable to viewed internal by the defendants’ demonstrated Virginia, v. U.S. prosecution,” Jackson testimony, and correspondence, deposition 307, 319, 61 L.Ed.2d 560 99 S.Ct. to the IRS. written submissions (1979), following facts. established of the tax shelters and Since the details I. Facts largely law are irrele- supporting tax briefly we summarize appeal, vant on group E Y a new & formed (necessarily oversimplified) operation designing strategies, tasked follows. shelters,”3 “high net these transactions as to market “tax jury agreement a limited 3. As the was instructed: plea contained 2. Bolton’s *9 appeal permitted him to appeal waiver that “tax refers to invest- term shelter” [T]he exceeding impris- any six months of sentence potential for ments that have the substantial application of U.S.S.G. based on the onment savings main benefits. tax as one of [their] exceed- legal; § Because Bolton's sentence 2T1.9. tax are other tax shel- Some shelters not, particular imprisonment depends and was based it all on the ed six months of ters are 2T1.9, appeal application § his is facts. on the A I: properly before us. 562-63/490-91. (“LLC”) A.The CDS Shelter purchase pair would a offsetting “digital”4 foreign currency op- The CDS shelter was a tax “deferral and tions that involved a bet on how particu- a strategy conversion” that allowed a tax- lar foreign currency perform would against payer ordinary to convert income into days. U.S. dollar in 30 Prior to the long-term capital gains and defer tax liabil- maturity options, of the taxpayer year ity to the after the income was would option contribute the contracts to an taxpayer earned. The a would form secu- investment partnership. After the options trading partnership rities in which the tax- expired, the investment partnership was payer partner served as limited and anoth- liquidated and the taxpayer’s interest entity general partner. er served as the partnership was transferred to a Sub- partnership engage large would then in a (“S chapter corporation S corporation”),5 volume trading of short-term and invest in which would sell the assets and realize a swap an 18-month transaction. Because deductible tax loss. of the “trader” partnership, status swap payments by partnership made C.The Add-On Shelter were expenses. deducted as business If The Add-On shelter was a tax strategy (ie., the swap early was terminated before marketed as a indefinitely means to defer maturity), months, pay- but after income liability capital on gains, includ- ments received the partnership were ing the capital gains generated in the sec- lower) (significantly taxed at the capital year ond strategy. CDS Like CO- gains rate rather ordinary than the income BRA, Add-On involved the purchase of rate. Treatment of payments these as offsetting digital option pairs, followed capital gains depended upon “early a designed series of transactions gener- termination” of the swap, which allowed ate a tax offsetting loss. The options were payment to be characterized as a “ter- structured so that there was a “one-pip” payment” mination under the applicable gap6 that, prices, between their strike so regulations. scenario, in a theoretical “home run” a taxpayer could make a multimillion dollar B.The COBRA Shelter profit. COBRA, Unlike CDS and howev-

The COBRA shelter was a tax “elimina- er, there was no possibility reasonable strategy tion” involved creating an earning profit from apart Add-On from asset with a high purposes, “basis” for tax scenario, the “home run” since the Add-On taxpayer which the could then sell and fee required payments structure to E & Y generate a deductible taxpayer loss. The entity acting and the as general partner liability would create a limited company potential payoff. exceeded the As a 'digital' option "A corporations referred 'pass-through' to as an to elect taxation —often 'all-or-nothing' option option whose system subjected under which income is —is payout long spot price is fixed as as the ex- only one level of corporation's taxation. The is, price; ceeds the payout strike does profits pass through directly to its sharehold- increase as the difference between the pro reported ers on a rata basis are spot price price and the strike increases.” the shareholders' individual tax returns.” Gov’t’s Br. 33-34 n.* *. C.I.R., 206, 209, v. 531 U.S. 121 S.Ct. Gitlitz (2001) (internal 148 L.Ed.2d 613 cita- Subchapter corporation corpora- 5. A S is a omitted). tions tion that makes a valid election to be taxed Subchapter under S of the Internal Revenue "one-pip” gap possible 6.A is the smallest §§ Code. See 26 U.S.C. 1361-1379. “Sub- "spread” option pair. in an chapter qualified S allows shareholders of *10 the After E & Y sold partners. & Y result, tax shelter was the sole Add-On sub- by the to a French developed consulting defendants arm of its business charges.7 tax evasion ject to substantive each Gemini in company Cap called an allocation of partner & Y received E The D. PICO Shelter Y part- Eleven E & Cap Gemini stock. a tax deferral The shelter was PICO Tradehill, which was participated ners an that involved strategy conversion and on the the tax due designed to eliminate with anoth- corporation in an S investmént Cap from the they recognized income pur- would taxpayer The er shareholder. transaction. Like COBRA Gemini corpora- the of the S chase 20% of stock Add-On, formation Tradehill involved tion, person another associated while corporate entities and of numerous (which firm Bricolage investment one enti- option pairs from contribution transaction) helped implement ty to another. remaining 80% inter- purchase would (also known as corporation est. The S were tax shelters We note that similar Corporation, or Personal Investment major account- by marketed and sold other “PICO”) purchase would then so-called part of a lucra- ing firms and law firms as “straddles,” financial instruments flour- practice that tive “tax avoidance” on offsetting gains and losses generated generally See The ished the late 1990s.8 rates, currencies, com- interest foreign Role Firms in U.S. of Professional in- a sufficient building up modities. After 109-54, Industry, S.Rep. No. Tax Shelter bets, the PICO would ventory “losing” (2005). 2000, the IRS February at 3 buy Under out the 80% shareholder. Analysis Tax created the Office of Shelter would regulation, the 80% shareholder tax notices subsequently issued a series of gains recog- allocated his share of be An at “abusive” tax shelters.9 directed to the time of by up nized the PICO Permanent April report issued gains and losses redemption, and all the Investigations on Subcommittee (i.e., thereafter most of the recognized Security Homeland Senate Committee on losses) taxpayer. would be allocated to the and Governmental Affairs stated to the contributing After additional assets “[ujnder law, single no standard current PICO, then take the taxpayer could The an abusive tax shelter.” Id. defines desired deduction. the past further noted that report “[o]ver E. Tradehill Shelter regulations years, Federal statutes have under- prohibiting illegal tax shelters shelters, the four tax Unlike the other clarify revision to only gone repeated marketed to E Tradehill shelter was Anderson], (Government’s selling and KPMG are the short A summa- 7. See III: 567/5548 tion) ("Now, (client inqui- strategy"); Two and Three of the option Counts A II: 92/1086 charge defendants with indictment all four ry Y a tax elimina- about whether E & offered evasion, respect Add- only with but presented strategy to that an- tion similar transaction, why empha- have and that’s I consulting group). other charged that the other shelters are not sized evasion."). as tax Guide, Technique Partnership 9.See —Audit http://www.irs.gov/ ch. available Indeed, supports case the record this Businesses/Partnerships/Partnership —Audit- that E & Y was not the first inference Technique-Guide Chapter-9—Tax-Shel — implement types of tax shelters at issue. The-Disclosure-Regime-(Revised-12- See, (internal noting ters — e.g., e-mail A IV: 114 26, 2012). 2007) (last visited Nov. firms, major law AA [Arthur that "seven *11 them.” Id. strengthen Although by this case United States impairing the lawful gov- require not us to comment on the (known does ernmental functions of the IRS revisions, of we think it substance those a “Klein conspiracy,” see United States v. acknowledge useful the law with Klein, (2d (2) Cir.1957)); F.2d to tax E respect shelters has evolved since to commit tax evasion in connection with Group & Y formed the VIPER in 1998. shelter, the Add-On tax in violation of 26 (3) 7201;12 § U.S.C. and to make false History II. Procedural IRS, statements in violation of 18 grand jury A federal returned a sealed § U.S.C. 1001.13 22, 2007, May indictment on and a su- Counts Two and charged Three each perseding February indictment evasion, trial defendant with tax in viola- 2008, charging the in thirteen defendants § tion of 26 in U.S.C. connection with a wide-ranging conspiracy counts to with the Add-On tax shelter. through defraud the United States the de- Counts Four and Five charged Nissenb- sale, velopment, implementation of the Coplan, aum and respectively, with ob- E Y superseding & tax shelters. IRS, structing the in violation of 26 U.S.C. indictment was redacted to seven counts § 7212.14 (the Indictment”) “Redacted for the trial Counts Six Nissenbaum, charged Vaughn and Seven Coplan, Shapiro, Coplan, respectively, making with Vaughn.10 IRS, false statements to the in violation of Count One of the Redacted Indictment § 18 U.S.C. 1001. charged each trial defendant with a con- 371,11 spiracy, 3, 2009, § in violation of Trial 18 U.S.C. commenced on March with (1) objectives: trial, three to defraud the beginning jury selection. At (a) Appendix A Except provided See for an overview of the as otherwise in this section, whoever, Redacted Indictment and Information. As any matter within the above, charged executive, noted David Smith was also jurisdiction legislative, of the or Indictment, Superseding fugi- but was a judicial branch of the Government of the tive at the time of trial. States, knowingly willfully— falsifies, conceals, (1) up by any or covers provides, part, 11. Section 371 in relevant trick, scheme, fact; or device a material persons conspire two or "[i]f more either to false, fictitious, any materially makes States, any against commit offense the United representa- or fraudulent statement or States, any agency or to defraud the United or tion; or any any purpose, thereof in manner or for any writing makes or uses false or persons any and one more or of such do act knowing document same to contain object conspiracy, to effect the each false, fictitious, any materially or fraudu- imprisoned shall be fined under this title or entry; lent statement or years, not more than five or both.” 18 U.S.C. title, imprisoned shall be fined under this § 371. years not more than 5 ... or both. 1001(a). § 18 U.S.C. provides, part, 12. Section 7201 in relevant "[a]ny person willfully attempts who 7212(a) provides, part, 14.Section in relevant any any manner to evade or defeat tax im- "[wjhoever corruptly by or force or posed payment this title or the thereof impedes, threats force ... obstructs or or shall, penalties provided in addition to other impede, endeavors to obstruct or the due ad- law, guilty felony.” be of a 26 U.S.C. title, shall, upon ministration this convic- § 7201. thereof, $5,000, tion be fined not more than 1001(a) imprisoned § provides, years, 13. 18 U.S.C. or than relevant more part: 7212(a). § both.” 26 U.S.C. *12 to 15 sentencing principally Bolton viction to demonstrate sought the Government million and a conspired imprisonment to conceal of $3 defendants months the tax of the five shelters the true nature fine. re- “cover stories” variety a of creating free on have remained The defendants of purpose purported business garding appeal. of this the resolution pending bail were shelters, in fact the shelters when avoid tax- solely by a desire to

motivated essence, DISCUSSION sought the Government es.15 In hid the that the defendants demonstrate fewer than ten raise no The defendants infor- by withholding from the IRS truth convictions respective to their challenges affirmative misstate- making and mation briefly which we appeal, on and sentences 7, 2009, jury returned May On ments. (1) the Govern- follows: summarize as on all counts. guilty verdict of general a theory legally was conspiracy ment’s Klein 2010, 22, 21 and the District January On (2) invalid, evidence there was insufficient prin- the trial defendants sentenced Court (a) Shapiro the convictions of support was sentenced cipally Coplan as follows: One, the con- on and Nissenbaum Count years three imprisonment, months of to 36 (b) of Sha- charge, the convictions spiracy $75,000 fine; release, a supervised and of and on Counts Two piro and Nissenbaum sentenced to 30 months Nissenbaum was (c) Three, charges, tax evasion and years supervised three of imprisonment, of Four, on Nissenbaum’s conviction Count release, $100,000 fine; a and (3) charge, the District the obstruction imprisonment, to 28 months of sentenced that venue was finding erred in Court release, a and years supervised two of Six, charged which proper for Count fine; $100,000 Vaughn was sentenced and IRS, false statements to the Vaughn with and two imprisonment to 20 months of (4) by admitting the District Court erred judg- release. The years supervised of coconspirator testimony alleged of for the trial defendants ments of conviction attorney who com- Taylor, a tax January Graham were entered on variety involving crimes mitted a of 22, 2009, trial, January Bol- Prior to on (5) case, unrelated to this shelters Superseding Infor- pleaded guilty to ton admitting the out- District Court erred of charging single him with a count mation than 20 al- of more of-court statements § in violation of 18 U.S.C. conspiracy, (6) the District Court leged coconspirators, (1) to defraud the having objectives: three and excluding portions Coplan’s of erred de- by impeding, impairing, States (7) transcripts, the de- Vaughn’s deposition govern- the lawful feating, obstructing and prejudiced by prosecutorial fendants were (the IRS so-called mental functions of the rebuttal misconduct in the Government’s (2) to make false conspiracy”); “Klein (8) summation, erred in the District Court IRS, in of 18 violation statements (a) give “theory de- declining (3) 1001; § ob- corruptly U.S.C. (b) instruction, jury instructing fense” impede the administration struct and (c) theory, and a conscious avoidance laws, of 26 internal revenue violation that “economic sub- 7212(a). 14, 2010, instructing jury April § On U.S.C. a “rea- only if there was con- stance” existed judgment entered a District Court to lack resulting quences. transactions are said Such can disallow deductions 15. The IRS ” Comm’r, Lee v. 'economic substance.’ that "can not [sic] from a transaction (internal substance, (2d Cir.1998) quota- purpose, F.3d be said to have reason omitted). and citations apart anticipated tax conse- tion marks utility from [its] possibility” profit, spillover place among sonable its the internal revenue meas- prejudice Coplan’s Vaughn’s infected ures and among general penal included convictions, remaining provisions. Bolton’s Id. 418 n. 36. In United Hirsch, procedurally sentence was substan- States v. 100 U.S. 25 L.Ed. 539 *13 (1879), tively unreasonable. the Supreme Court held that the

conspiracy provision generally applica- Validity I. of the Government’s ble to the body whole of federal law. In so Theory Conspiracy

Klein holding, the prohibit- Court described the “any ed fraud as against fraud United [the appeal The first issue on concerns the coin, may against It be States]. the or legal validity of the Government’s Klein consist in cheating government of its conspiracy theory under the “defraud property.” land or other Id. at 35. § previous- clause” of 18 371.16 As U.S.C. noted, ly Count One of the Redacted In- “It is a well-established rule of con Nissenbaum, charged Coplan, dictment struction that Congress where uses terms § Shapiro, Vaughn conspiracy in a 371 that have accumulated settled un meaning (1) objectives: with three to defraud the law, der ... the common a court must (the (2) conspiracy), United States Klein to infer, dictates, unless the statute otherwise taxes, evade to make false state- Congress means to incorporate the objective ments to the IRS. The core established meaning of these terms.” argued by the Government at trial was the States, 1, 21, Neder v. United 527 U.S. 119 conspiracy, Klein and that conspiracy 1827, (1999) (internal S.Ct. 144 L.Ed.2d 35 primary forms focus of the defendants’ omitted) quotation marks and alterations arguments on appeal. (omission law, in the original). At common the words “to defraud” deprive meant to Origins

A. The of the property rights by another of dishonest Conspiracy Klein means.17 See Hammerschmidt v. United 1867, States, 182, 188, 511, original Enacted federal 265 44 U.S. S.Ct. 68 (1924); conspiracy appended statute was to “An L.Ed. 968 Porcelli v. United (2d Cir.2002) States, 452, existing relating Act to amend Laws 303 F.3d 457 n. 1 Internal Revenue and other Purposes.” (noting the “familiar common law ‘ ’ Goldstein, Conspiracy Abraham S. to De- meaning” of the term “fraud” involved States, 405, “using falsity money United 68 Yale L.J. to do the victim out of fraud interests”). 2, 1867, 418 Act (quoting property of March or Other federal 484). 30, § ch. generally Stat. the 1875 criminal statutes are in accord. codification, See, Pierce, the statute e.g., was moved from United States v. 224 F.3d prohibits conspiracies advantage; gaining 16. Section 371 all ar- ei- unlawful or unfair any against ther "to commit Unit- offense right tifice which the or interest of another (the clause”), ed or deceit; States” "offense "to de- injured; injurious stratagem; is States, any agency fraud the United or thereof Dictionary trick.” Id. at 541. The American (the any any purpose” manner or for "de- English Language, published by Noah of clause”). § fraud 18 U.S.C. 371. 1864, is, course, Webster of to be Heritage confused with the American Dictio- dictionary day, In the authoritative nary English Language, published by deprive "defraud” was defined as "[t]o Houghton any Mifflin in or modern fraud, right by deception or artifice.” The dictionary bearing great the surname of the Dictionary English. Language American lexicographer. American (1864). "Fraud” was defined as "[d]e- ception deliberately practiced with a view to by interfering (2d Cir.2000) (“In States of defraud the context fraud, military I draft words ‘to War fraud and wire World mail wronging ‘to one and circulation commonly through printing refer defraud’ meth- rights by subject dishonest to the draft property urging in his those handbills ” marks (quotation re- obey Supreme ods or schemes’.... it. The Court not to omitted)). § hold- convictions under versed the the Unit- conspire to defraud ing “[t]o

Nonetheless, the word “defraud” to cheat the primarily ed States means much more interpreted § has been money, but property out of government understanding of broadly. The current obstruct to interfere with or it also means liability may be “conspiracy to defraud” *14 by functions governmental of its lawful one Supreme Court traced to two seminal deceit, by at least trickery, or or Henkel, case, v. In the Haas cases. first craft Hammer- means that are dishonest.” 462, 249, 54 L.Ed. 569 216 30 S.Ct. U.S. 188, schmidt, at 44 S.Ct. 511 265 U.S. (1910), obtained advance the defendants added). the Because defen- (emphasis employed from a statistician information Ser- of the Selective Agriculture “open in order dants’ defiance” by Department the of in the or other advantage a Act devoid of deceit gain speculating to vice The invoked grain trickery, Supreme futures market. Court held the Court the word “de- expansive reading scope of fall within the their conduct did not 189, the defendants’ conduct bring § fraud” to 44 511. of 371. Id. at S.Ct. Specifically, statute. conspiracy within at conspiracy The Klein doctrine held that “it is not essential Court progeny is the of Haas issue here contemplate a fi- conspiracy such a shall Hammerschmidt,18 v. States United The or that one shall result. nancial loss (2d Klein, Cir.1957), 908, 247 F.2d 916 in enough is broad its terms statute charged with tax evasion defendants were of any conspiracy purpose for the include in connection conspiracy” and a “defraud obstructing, defeating or impairing, selling Id. at whiskey with their business. gov- any department lawful function of judg The district court entered 915-16. 479, 249. ernment.” Id. at 30 S.Ct. acquittal on the substantive ments later, in Hammer- years Fourteen counts, jury convicted on the re and the States, 182, 265 44 schmidt v. United U.S. ap § count. On maining conspiracy 371 (1924), 511, S.Ct. 68 L.Ed. 968 Court sup evidence to peal, we found sufficient attempted expansive to retrench from § conspiracy 371 conviction based port § in In the words of reading of 371 Haas. income,” twenty on “acts of concealment Dean) (later, Gold- Professor Abraham S. tax returns including false statements on School, expan- Yale Law stein of the “[t]he at responses. Id. interrogatory ... reading sive of the statute Haas Hammerschmidt, we Relying 915. a finally Supreme attempt led the Court to held that systematic judicia- examination of what the [mjere failure to income would disclose v. ry wrought. had Hammerschmidt to show the crime not be sufficient States furnished the occasion.” United (footnote States defrauding the United Goldstein, charged Yale L.J. 429 68 at statute, omitted). § under 18 U.S.C. 371. defen- The Hammerschmidt however, cheating only includes conspiracy a dants were convicted of Indeed, mary holding quotation from conspiracy” of Klein is appellation "Klein misnomer, pri- Hammerschmidt. is in some sense a since

61 of the government property out of or conspiracy to defraud the Govern- money, but “also means to interfere with ment is to be read broadly more than a governmen- conspiracy or obstruct one of its lawful private person. defraud a deceit, Goldstein, by tal functions trickery, craft or See 68 Yale L.J. at 424. Dicta McNally States, at v. least means that are dishonest.” 483 U.S. (1987), S.Ct. L.Ed.2d 292 Hammerschmidt, (quoting Id. at 916 example, accepted such a distinction. 511). Thus, U.S. at S.Ct. order Quoting a decision of the of Appeals Court prove a Klein conspiracy, the Govern- Circuit, for the First Supreme Court “(1) ment must show defendant [the] “ stated that ‘[a] statute which ... has for (2) agreement entered into an to obstruct a object its the protection of the individual lawful function of the Government property rights of the members of the deceitful or dishonest means and body, civic thing; is one a statute which least one overt act in furtherance of the object has for its protection and wel- Ballistrea, conspiracy.” United States v. alone, fare of the government which exists (2d Cir.1996) (alteration 101 F.3d purpose for the of administering itself in omitted). *15 the interests of the public, quite anoth- [is] ” 8, er.’ Id. at 359 n. to Klein Challenge 107 B. (quot- S.Ct. 2875 The ing States, Curley 1, v. United 130 F. 7 argue vigorously defendants ap- on (1st Cir.1904) (alterations original)). in peal that the conspiracy theory Klein is But this conclusion appears to on rest textually unfounded. The Government’s policy judgment that, in the nature of — stare decisis defense of the Klein doctrine things, government justify interests broad- view, support lends to this as it rests en- protection er that the private interests of tirely § on the construction of 371 in Ham- parties than any on principle of —rather merschmidt. There is nothing the Gov- statutory interpretation. ernment’s brief recognizable statutory interpretation plain discussion of Notwithstanding —no these infirmities meaning, legislative history, interpretive or history the and deployment of the stat Indeed, canons. pages all 325 of its ute, it § is now well established that 371 brief, the Government quote does not even “is not confined to fraud as that term has § the text of 371. The Government thus law,” been defined the common but appears implicitly to concede that “‘any conspiracy reaches purpose for the conspiracy crime, Klein ais common law impairing, obstructing defeating created courts rather than Con- any lawful function of department of Gov ” gress. That fact alone warrants consider- States, ernment.’ Dennis v. United 384 judicial able skepticism. See United 855, 861, 1840, U.S. 86 S.Ct. 16 L.Ed.2d Lanier, 259, 6, States v. 520 U.S. 267 n. (1966) Haas, 973 (quoting 479, 216 U.S. at 1219, (1997) 117 137 S.Ct. L.Ed.2d 432 249). (whose Indeed, 30 S.Ct. Coplan (“Federal crimes are by Congress, defined counsel “takes the laboring oar” on the court....”); not the Rogers see also v. issue) conspiracy Klein “readily concedes Tennessee, 451, 476, 532 U.S. 121 S.Ct. that, weight were the of this Circuit’s case 1693, (2001) (Scalia, ./., 149 L.Ed.2d 697 matter, law outcome-determinative in this (“[T]he dissenting) notion of a common-law challenge his government’s Klein utterly crime is today....”). anathema theory would fail.” Coplan Reply 3. justify To an expansive reading Although argue defendants forceful- § courts have occasionally implied ly appeal on that we should follow the

62 — Yannotti, novo, States, 541 States v. de United Skilling v. example of United (2d Cir.2008), 2896, 2928, uphold will 120 we -, 177 130 S.Ct. F.3d U.S. (2010), “any if ration- body judgments of conviction “pare” L.Ed.2d 619 core,” id., have found the essen- to its al trier of fact could § “down precedent beyond the crime a reason- to a tial elements of properly are directed arguments such doubt,” Jackson, ap- able U.S. authority. As an intermediate higher court, are bound to follow S.Ct. 2781. we pellate no Supreme precedents, Court dictates of argu- find the persuasive we

matter how Sufficiency of the Evidence A. the moor- breaking loose from ments for Supporting One Count by “par- judicial norms ings of established Nissenbaum Shapiro and Defendants ' ing” a statute. sufficiency of the evi- challenge first sum, de- because the Klein doctrine three with to each of the respect dence of the scope falls within the rives from and § conspiracy. alleged objectives of (itself long- grounded law of the Circuit noted, Count One previously As decisions), reject we Supreme lived Court charged the trial de- Redacted Indictment validity challenge to the the defendants’ § three conspiracy in a fendants theory liability. of criminal (1) to defraud objectives: (the to evade conspiracy), Klein States Sufficiency Challenges II. The taxes, § in violation of 26 U.S.C. le challenging In addition IRS, in to make false statements theory, validity conspiracy of the Klein gal § 1001. violation of 18 U.S.C. *16 Shapiro and Nissenbaum defendants convic conspiracy “To sustain a sufficiency challenges.19 mount a series of tion, some matter, present the Government must challeng a defendant general As a reasonably it can be that led evidence from which sufficiency of the evidence ing the person charged with con heavy a inferred that to his conviction at trial “bears Heras, the existence of the burden,” spiracy F.3d knew of States v. 609 United (2d Cir.2010) and alleged in the indictment 101, (quotation marks scheme 105 in it.” omitted), joined participated knowingly of review is “ex as the standard 539, F.3d deferential,” Rodriguez, v. States v. 392 States United ceedingly United (2d Cir.2004) (2d Cir.2008). 108, marks omit Hassan, (quotation 545 F.3d 126 578 ted). conspiracy In context of a con sufficiency challenge, we evaluating a viction, jury’s findings to the is light in the most “deference “must view the evidence ... a con especially important ev because government, crediting favorable very nature is a secretive spiracy have been drawn its ery inference that could where all favor, operation, and it is a rare case deferring to government’s in the laid bare in credibility aspects conspiracy of a can be of witness jury’s assessment Rojas, 617 F.3d of the court.” States v. weight of the and its assessment Cir.2010) (2d Chavez, 669, marks (quotation 674 v. evidence.” United States omitted) (alteration Where, Cir.2008) (internal (2d original). 119, cita F.3d here, jury guilty “a returns a verdict on tions, marks quotation alterations omitted). acts in the charging an indictment several Although sufficiency review is Coplan challenges argument sufficiency ic of his own. Vaughn joins Shapiro’s re- 19. insufficiency evidence to garding sufficiency challenge. of the a does not raise conspiracy, specif- no prove a Klein but raises summation, if conjunctive, ... the verdict stands the were not true. In rebuttal respect any Government argued you evidence is sufficient credit “[i]f Mr. charged.” Dougherty’s testimony, one of the acts v. Unit- ... that alone Griffin States, 46, 56-57, 112 proof beyond ed 502 U.S. S.Ct. is a reasonable doubt on the 466, (quotation 116 L.Ed.2d 371 conspiracy count at least as to ... Mr. omitted). reason, marks For that “the Shapiro.” On appeal, the Government support lack of sufficient evidence to one similarly argues Dougherty’s testimo- objects multi-object of the conspiracy ny ... “standing alone would be sufficient conviction, conspiracy vitiate the [will] support his conviction on the false state- sup- where there sufficient evidence to [i]s Indeed, ments object conspiracy.” of the port object.” United States v. [another] variations on the assertion that Cir.1996). Pascarella, (2d 84 F.3d Dougherty “coached” appear lie no few- er than four times in the Government’s follows, In what we consider the 67, 112, 117, brief. See Br. Gov’t’s conspiracy against evidence defendants Nissenbaum, Shapiro and mindful But the respect Dougher- record with conspiracy character and effect of a “[t]he ty’s testimony is considerably equivo- more judged by dismembering are not to be it cal than in the Government’s account. viewing separate parts, only by its but April Dough- Call. whole,” Conference looking at it as Cont’l Ore Co. v. erty testified that in March he ad- Corp., Union Carbide & Carbon 370 U.S. Coplan vised that the IRS auditing 690, 699, 82 S.Ct. 8 L.Ed.2d 777 Lake WRB transaction20 —the first such omitted). (quotation marks Never audit of a COBRA transaction. In re- theless, clarity for the sake of and ease of sponse, Coplan informed Dougherty that analysis, examine the evidence with we Conlon, attorney Dennis in E & Y’s respect alleged objective to each practice, national tax would coordinate conspiracy some detail before consider 2, 2001, response. April audit On Dough- ing conspiracy “as a whole.” For the erty participated a conference call with follow, reasons that we that the conclude *17 Coplan and that Conlon involved discus- respect evidence with to the intent of Sha may presented sion of “ideas that be piro and Nissenbaum is insufficient to sup why agent steps for did the [the clients] port their convictions on Count One. they executing that did” the COBRA Conspiracy Evidence Following transaction. the initial confer- Against Shapiro call, ence indicating Conlon sent e-mail that, “I think [Shapiro] we need Richard Objective Conspiracy a. Klein the “I meeting,” first because want to state The centerpiece conspiracy clearly correctly our case from the E Y against Shapiro, partner case an & beginning.” lawyer nearly and tax with four decades’ 21p, experience, April is the Government’s claim that Call. On Conference 24, 2001, April Dougherty participated he E & Y partner “coached” Thomas Conlon, Dougherty Coplan, to lie to the IRS him conference call with helping up explanations Shapiro. According Dougherty’s come with non-tax for the con- notes, Shapiro temporaneous Shapiro COBRA transaction that knew raised the partners 20. The "WRB with the Lake” transaction was a CO- who executed the shelter Dougherty. BRA named transaction for three business assistance of respect to is slim at best. With assertions of the CO- purpose the business topic of call, Dough- 2001 conference April the call. during BRA transaction asked a Shapiro indicate that erty’s notes Meeting. Preparation May is the business question: “What single 16, 2001, May that on testified Dougherty prep- During May purpose?” Rich- meeting prepare led [a] “Conlon meeting, Shapiro— aration Conlon—not meeting our myself Shapiro ard IDR, antici- meeting, reviewed led At that meet- day with the IRS.” the next and coordi- potential questions, IRS pated assignment of coordinated ing, Conlon what ... talk about nated “who [would] meeting, re- for the IRS topics discussion Contrary meeting. topics” at the the IRS In- points the relevant viewed assertion, Dougherty testi- Government’s (“IDR”), Request formation Document Shapiro on cross-examination fied ... that would come “anticipated questions sug- to lie” and did not “never told [him] meeting.” up during the IRS IRS in order to conceal gest lying to the Meeting. The follow- May 2001 IRS transaction. “problems” with COBRA Conlon, Shapiro Dougherty, and ing day, Dougherty further testified Crucially, the WRB met with the IRS to discuss Shapiro [COBRA] himself “believed During that transaction. Lake COBRA law.” worked under the falsely represented meeting, Dougherty testimony, Beyond Dougherty finan- E & Y “mentioned the tax and Shapiro claims that en- Government also foreign currency invest- implications cial that, not “in- in various acts while gaged in the the clients involved WRB ments” to “in the herently deceptive,” deceptive were transaction, “be- Lake and that the clients case,” of this as follows. context in the COBRA transac- came interested” testified at Dougherty tion as a result. The Govern- Promotional Materials. foreign in fact discussion of trial that his participation for his Shapiro ment faults currency with the clients was investment personnel policy discouraging E & Y’s “strictly limited to discussions we had and other leaving from PowerPoint slides transac- of the COBRA presentation clients, in case marketing materials tion,” he “lied the IRS [to and that had those copies the IRS should demand the reasons for agents] [the clients] about during from the client an audit. materials transaction.” entering into the COBRA See, (Shapiro stating A e-mail e.g., V: that he had Although Dougherty testified not be materials should presentation “the real facts” about how Shapiro told client). The Government left with the Young clients “had come to Ernst & WRB and others enforced claims that *18 transaction,” the he did not COBRA marketing the mate- policy prevent this to the substance of that conver- elaborate on rials, step which out each of the under- laid sation. transactions, into the falling from lying facts, the IRS. The Government does the Government re- hands of On these however, IRS ever argue, that the “Dougherty testified peatedly asserts mate- copies promotional requested in consultation with Co- specifically that files, IRS,” or that held in E & Y’s own he lied to the and rials plan Shapiro, required E & Dough- governing ethical standards “Coplan Shapiro coached in the ab- Y to those materials erty false information to the disclose provide to request.21 support for these sence of such a IRS.” But the record ¶ Conduct, (2006) (reaffirming principle pmbl. 9 basic Prof’l ABA Model Rules of Cf. Similarly, ing the Gov- account active” in Early light Termination. of the “upside highlights Shapiro’s side”); ernment editorial and no down id. at 219. The Gov- on an internal “Action Plan” comments argues ernment that this advice “was de- steps that summarized the involved signed protect to the bogus descriptions of tax his E & Shapiro CDS shelter. advised CDS.” Gov’t’s Br. 122. There is no dis- Y to colleagues avoid references to however, pute, that the substance of the “early” swap termination of the CDS con- advice advocated lawful trading activity. tracts.22 The Government characterizes Review Finally, PICO Documents. of Shapiro’s advice an as “underhanded ef- points the Government to Shapiro’s devel- protect descriptions to fort[ ] CDS opment and review of various documents designed that were convince agents to related to the PICO shelter as evi- something defendants knew to be dence of his “involvement in providing (internal false.” Gov’t’s Br. 122 quotation false directly information to the IRS.” omitted). marks As the Government re- Gov’t’sBr. 135. example, For the Govern- concedes, however, luctantly the CDS highlights ment Shapiro’s involvement in swap provided party contracts that either drafting the opinion PICO letter with out- could elect to swap terminate the before counsel, side maturity Cinquegrani, Peter imposed date —but no obli- who was Indeed, gation special to do so. several then counsel at clients Arnold & Porter. inquired about continuing swaps alia, argues, The Government inter maturity they date because were “interest- opinion letter misleading contained profits,” ed in the swap and were told that statements because it described PICO as income, doing so would lead to deferral of “opportunity an personal create invest- but not ordinary capital conversion from ment companies,” A V: when the end, gain. In the swap no CDS extended “real reason” for the transaction “was to past early termination date. Although provide investors,” tax losses for A III: Shapiro’s edits to the CDS “Action Plan” Cinquegrani, the self-described 114/3756. clearly deemphasized prevailing expec- letter, “principal opinion wordsmith” of the termination, early tation of it appears testified at trial opin- that he intended the the revised version was in fact more accu- ion misleading letter to be because his summary rate in its of the swap contract “intention was to describe the transaction terms. much possible ordinary as as as an busi- downplay ness deal and to all the tax Keep Trading

Advice to CDS Account aspects.” There is little such evidence Open. example decep- As additional context,” with respect Shapiro’s intent. The rec- tion “in the Government points to ord of suggestion by Cinquegra- communication between Coplan, Shapiro, and Nis- ni and reflects a trading Shapiro senbaum that CDS clients continue sometimes tense working relationship, in which past early termination date in re- order argument peatedly questions their tax as raised strong “mak[e] concerns 214; (Sha- possible.” language A IV: see id. at 212 about the draft opinion. piro e-mail advocating “keeping the trad- See A III: (Cinquegra- 144/3873-145/3876 *19 lawyer's obligation zealously pro- priate during of “the swap period, time the will GP interests, pursue legitimate tect and a client’s swaps terminate the with the bank.” In re- law”). within the bounds of the advice, sponse Shapiro’s Step 45 was edit- read, "Swap ed to terminates.” original 22. In the draft of the CDS Action Plan, Step appro- 45 read follows: “At the faith good consistent with appears equally as “a describing Shapiro testimony ni tasked with because he role as a “technician” “high maintenance” his pain” and questions ask the same struc- frequently “would the transactions were making sure the and “would revisit multiple times” law. compliance with tax Id. tured been ad- previously that had same issues testimony); see (Cinquegrani 140/3857-58 dressed”). ex- example, Shapiro For (Six testimony); A II: also 544-45/2865-67 that “the nature of the “concern” pressed testimony).23 (Rydberg III:A 398/4882 making ... investors are rep[resentation]s A 455. On strong.” IV: may be too Objective Tax Evasion b. occasions, revi- Shapiro proposed several incorporated into Cinquegrani sions that Shapiro challenges also result, early a an As documents. PICO respect to sufficiency of the evidence with that PICO clients had representation § objective tax evasion was re- purpose investment “principal” “It is charged in Count One. conspiracy representation PICO placed crime, conspiracy is a elementary that nontax business had a “substantial clients and distinct from the substantive separate Shapiro purpose.” A III: 165/3955-56. Pinckney, 85 States v. offense.” United opin- a draft version of questioned also (2d Cir.1996). “Although the F.3d inaccurately suggested ion letter prove need not commission government transac- consequences tax of the PICO secure a con offense” to substantive A not discussed with clients. tion were conviction, prove “it must that the spiracy result, opinion the final 457. As a IV: conspirators] conduct intended future [the inves- potential letter disclosed that PICO upon includes all the elements of agreed an overview of the “provided tors were (internal quo the substantive crime.” Id. trading strategy, includ- economics of the omitted). tation marks and alterations A consequences.” tax V: ing potential case, the substantive crime of tax this 575. “(1) proof of the exis requires evasion argues strenuously The Government debt, willful tence of a substantial tax opinion final letter still appeal that nonpayment, and an affir ness of the misleading statements contained lies and defendant, performed mative act the “real reason” for the PICO about to evade or defeat the calcula with intent that, But we note as Cin- transaction. of the tax.” United payment tion testified, very himself quegrani fact (2d Litwok, 208, 215 States v. 678 F.3d prepared letter was indi- opinion Cir.2012) omitted); see (quotation marks anticipated cates that the client substantial § U.S.C. A III: tax benefits from the transaction. deficiency Government’s sole tax Thus, to fault be- 146/3880-81. theory at trial was that the Add-On opinion affirmatively letter failed cause offered investors no reasonable shelter to state that the “real reason” for the and that the tax losses possibility profit, provide transaction was “to tax loss- PICO therefore could not resulting from Add-On spurious. At a mini- es” borders on from the investors’ mum, properly be deducted with Shapiro’s respect conduct argued tax returns. The Government crafting opinion letter PICO analysis objective of that evasion below. Our 23. For the sake of convenience and to avoid is, course, equally applicable in repetition, the evidence evidence undue we set forth objec- conspiracy Shapiro’s with the Klein respect involvement in the connection the tax tive. Add-On tax shelter under the rubric of *20 that, explana- in to create a non-tax involved in drafting order factual section of the Add-On tion for the mechanics of letter, legal the Add-On opinion and was transaction, adopted trial a defendants from excluded e-mails which others dis- story” proposed by false “cover Bolton. cussed economics of the transaction. story key step That cover attributed a Marketing. Add-On The Government’s transaction —the transfer of the Add-On claim that Shapiro was involved in market- digital options partner- from the individual ing the primarily Add-On shelter rests a a ship newly request formed LLC—to receipt his of various e-mails. In June Krieger from trader Andrew to consolidate 2000, Coplan Vaughn, Shapiro, sent accounts for administrative convenience. meaningful dispute There was no at trial a proposed Nissenbaum e-mail to other E story” the “consolidation cover was professionals & Y announcing the new false. shelter, Add-On and asked them to review “accuracy for and tone.” AIV: 127. That argues

The Government that sufficient repeated e-mail the consolidation cover supported objec- evidence the tax evasion story. Similarly, July Coplan tive sent because involved “w[as] junctures develop- critical of Add-On’s an e-mail asking Vaughn, Shapiro, Nis- ment, marketing, and defense.” In what senbaum, and others to “make any final follows, we consider evidence with re- changes” to a draft client solicitation let- spect to Shapiro’s involvement at each of contrary ter. But to the Government’s junctures.” these “critical assertions, there Shapi- is no evidence that actually ro habitually “reviewed” the Development. parties Add-On do dispute strategy not that the for the Add- Add-On solicitation they letters before On tax initially proposed by shelter was Indeed, were sent to clients. according to Vaughn developed by and thereafter Six, testimony cooperator trial of Belle Vaughn, Coplan, and members of the in- Shapiro among was not the people who operated by vestment firm Bolton. Al- “part process” “sending were of th[e] though Shapiro copies early received e- out A to clients.” II: letters 424-25/2391- describing “precursor concept” mails a 93. shelter, the Add-On participated Shapiro maintains that he had no reason telephone prelimi- conferences about that suspect understand or the economics of idea, nary “specifics” of the transaction February the Add-On shelter until only A developed subsequently. were III: years marketing after the Add-On (this 237/4241; see AII: was “not 2003— 496/2674 campaign he received draft “Talk way ultimately the Add-On transaction —when be”). ing Points” that contained the details nec Moreover, Shapiro came to did essary profit potential to assess the early attend an at which the al- meeting discussed, draft, leged story” reviewing “cover was not transaction.24 After "objective” prong jective objective pre-tax purpose Under the so-called business doctrine, profit potential) the economic substance transactions that must be satisfied before may profit potential lack a will be disallowed transaction be accorded tax benefits Libin, claimed.”); Congress the IRS. See Jerome B. see also Modem Tax Controver- sies, 478-1, Practicing Should Address Tax Avoidance Head-On: The Law Inst. 478-35 GAAR, ("To analyze pres- Internal Revenue 30 Va. Code Needs transaction for substance, ("Some objective Tax Rev. 345-46 lower ence of economic courts objective potential courts have viewed ‘economic substance’ as a look to see if there is an risk.”). (sub- having separate requirements profit presence genuine test two and/or *21 amnesty template, ments on the Add-On “the 2:1 ratio”25 asked whether Shapiro does not reflect although was “correct” the record describing potential payoff suggestions. of fees” was on or content of his impact scope and what “the then leaving transaction. Shapiro of the faults profitability Government .He in Coplan “[apparently, amnesty from learned in the story cover undisturbed payoff 2:1 would not apparent [A]dd-[0]n it not at all template, but is to E & Y paid exceed the transaction story cover in fact knew that the Shapiro fees of the loss totaling Bolton 1.5% and argues “bogus.” The Government was under premium net was amount since the an “instant Shapiro that because had seen added). The (emphasis A 1%.” V: Vaughn proposing message” from why explanation for offers no Government the “consol- he knew that concept, Add-On ratio payoff ask Shapiro would about But purpose was false. idation” business already knew that impact of fees if he exchange message in the instant nothing profit potential. lacked the Add-On shelter pur- business suggested that the Add-On instead, false; story the cover pose The Government was Add-On Defense. that, calls and by “reviewing developed during was conference argues further in an IRS de- Shapiro for use in which approving” correspondence e-mail chart af- himself committed an position, Shapiro participate. did chart at act of tax evasion. The firmative depicted the “home run” “sweet

issue Objective c. False Statement in which the Add-On shel- spot” scenario huge windfall to the produce ter would objective and final The third the Government con- Although client. Shapiro conspiracy imputed § 371 on the at trial that “the numbers ceded One, the false state- charged Count true,” argues it that the chart chart are objective, clearly directed to ments by attempt- the IRS was used to mislead Six and charged the conduct Counts a false non-tax motivation ing to establish (“Section A Seven. See VI: 420/6161 response, Shapiro for a transaction. only charged object as an is not no evidence that he argues that there is conspiracy, charged but is also Counts chart, affirmative with the anything did of- separate substantive Six and Seven as variety correctly which sets forth a of out- Coplan and against fenses defendants transaction, including the comes for the ”). noted, previously Vaughn.... As run.” At extraordinarily unlikely “home charged Six and Seven defendants Counts most, reflect that Shapiro’s time records Vaughn making false Coplan and a half. “he reviewed it” for an hour and IRS. The Government statements to the even knew Shapiro does not contend that Finally, points the Government to corre- Vaughn depositions Coplan about the the Add-On “amnes- spondence regarding occurred, they before much less discussed template” Shapiro’s par- as evidence of ty There was no testimony It their with them. conspiracy.26 in a tax evasion ticipation substantive false statements provide separate did com- appears premium) In December the IRS announced (profit: 25. The "2:1 ratio” refers to amnesty program taxpayers who under which that, unlikely highly "home the fact absent voluntarily engaged could had in tax shelters post, potential scenario discussed run” to the IRS order disclose those transactions payoff transaction before fees Add-On potential penalties. The defendants to avoid the net investment amount.” was "two times amnesty templates that E & helped craft Y’s clients could submit to IRS. *22 Conspiracy charge against Shapiro Against connection with Evidence deposition. his own IRS Nissenbaum Conspiracy d. The “As a Whole” Conspiracy Objective a. Klein Having reviewed the record and Amnesty Template. PICO The princi- counsel, arguments we conclude pal conspiracy against evidence Nissenb- against Shapiro the evidence is insufficient aum relates to his participation in the de- support to his conviction on One. Count velopment of amnesty the PICO template. conclusion, reaching this we are mindful 26, See note ante. The Government as- that the absence of direct evidence is not “drafted, serts that Nissenbaum and then dispositive, government since “the is enti Shapiro circulated to and Coplan for their prove solely through tled to its case cir review, template evidence.” a for the amnesty cumstantial United States v. PICO (2d Cir.2004). 539, Rodriguez, 392 F.3d 544 strongest submission.” The evidence to Nevertheless, the evidence viewed “[i]f support the Government’s assertion is a the light most favorable to the prosecution February 2002 e-mail Nissenbaum sent gives equal nearly equal circumstantial Shapiro to and Coplan with the draft a support theory guilt theory and a template PICO attached. The text of the innocence, then a jury reasonable must- “Gentlemen, e-mail reads as your follows: necessarily entertain a reasonable doubt.” Bob, you comments. did also want me to Huezo, United States v. 546 F.3d template [referring do SDI ato differ- (2d Cir.2008) (internal quotation marks ent Because the shelter]?” PICO omitted). case, In this an essential ele template misleading contained false and conspiracy ment of the charged Count transaction, descriptions of the the Gov- required proof beyond One a reasonable ernment claims that Nissenbaum knowing- Shapiro joined alleged doubt that con ly participated in providing false informa- spiracy with “specific intent” to violate directly tion to the IRS. But again, once Ogando, the law. v. United States the record belies the Government’s gloss. (2d 102, 107-08 Cir.2008); F.3d Rodriguez, Dougherty testified that he “drafted the (“To 392 F.3d at 545 conspiracy sustain a amnesty temp- [PICO] letters based on a conviction, government present must kit,” late from the SISG tool and that the some evidence from which it can reason template “generally opinion tracked the ably be inferred that the person charged letter” for respect the transaction. With conspiracy with knew of the existence of to Nissenbaum’s role in developing alleged the scheme in the indictment and template, Dougherty testified as follows: it”) knowingly joined participated added) (emphasis (quotation marks omit My recollection was that Martin Nis- ted). The evidence with respect Shapi senbaum temp- reviewer of the intent, light ro’s viewed in the most favor prepared pro- late letters that I and he Government, remains, best, able to the vided some non-substantive comments in equipoise. Because would not “[i]t sat on the final go version letters to isfy the jury to have a deter [Constitution] out to the clients. mine that the defendant is probably A II: further Dougherty testi- Louisiana, guilty,” 235/1641. Sullivan v. 508 U.S. 275, 278, fied that the “non-substantive comments” S.Ct. L.Ed.2d 182 (1993), provided Nissenbaum were to “take out Shapiro’s we conclude that convic tion on typo.” Count One must be reversed. the bold” and “correct[ ] various Add-On documents review of Trading Account Keep CDS

Advice in the Klein participation of his the ex- evidence regarding The e-mail chain Open. account, Coplan In March sent conspiracy. trading raised of the CDS tension Nis- above, amnesty template to see Part Add-On draft respect & Y II.A.l.a, ante, conspir- senbaum, in the and another E Shapiro, features also *23 In a No- look it over “to request Nissenbaum. with a acy against employee case e-mail, asked Sha- make it easi- Coplan unnecessary facts or to vember avoid Twenty about a shelter min- accurately.” and Nissenbaum CDS piro complete er to terminated, later,27 swaps replied have with a in which Nissenbaum “[t]heir utes partner- that the suggesting Bolton is but e-mail: three-line essentially 13.5 down after ship be shut except fine to me looks disclosure Coplan’s question A 219. months.” IV: necessary to I believe that it’s don’t E & Y should “intercede and was whether option each trade specifics of put year out with the suggest running another here, presumably If we do it the letter. respond- Nissenbaum trading account?” the hundreds of we’d have to include way too anxious to They ‘Yes. sound ed: trades that are done PICO. exchange, the Gov- From this get out.” re- Nothing in Nissenbaum’s Id. at 400. defendants argues “[t]he ernment “stamp ap- of knowing evinced a sponse . understandably concerned about the were story in cover for the consolidation proval” get anxious to taxpayers appearing ‘too Similarly, amnesty template. the Add-On account because that trading of the out’ July a 2000 e- also received Nissenbaum hasty would undermine false de- exit Coplan suggesting that Nissenb- mail from in- trading account as an scription of the “any final aum others should make vehicle.” vestment client solicita- changes” to draft Add-On that, of it in the context appears But But, Shapiro, there is tion letter. “they” exchange, pronoun the e-mail actually that Nissenbaum “re- no evidence e-mail is in Nissenbaum’s two-sentence letters; the Add-On solicitation viewed” “taxpayers.” not a reference to anxious of “part process” he of th[e] nor was Coplan’s initial appended The e-mail out letters to clients.” “sending Hasseltine, from inquiry was a note Cam Objective b. Tax Evasion firm, Bolton which was employee an trading accounts. managing CDS alleged tax evasion respect With e-mail, suggested which Hasseltine’s § conspiracy, Nissenb- objective of account, was ad- termination of the CDS similarly that the evidence is aum contends Six, Coplan, Belle dressed to Robert partici- Nissenbaum did not insufficient. employees E & Y two other —not meetings conferences or pate telephone anyone If clients at issue. taxpayer of the Add-On development related to the get anxious to out” of CDS shel- “too Although Nissenbaum occasional- shelter. ter, manag- employees it was the Bolton copies correspondence of e-mail ly received accounts, taxpay- not the ing trading Add-On, re- appears it that he related to the transaction. ers who entered three-line e- only once—in the sponded Indeed, the Govern- Finally, quoted mail above. Documents. Review Add-On acknowledge the dearth appeared ment points to Nissenbaum’s the Government computers the two that the clock on one of stamp Coplan’s initial e-mail 27. The time a.m.; stamp the time on Nissenb- was 9:16 was off one hour. Thus, appears reply it aum’s was 8:36 a.m. ILAl.b, to Nissenbaum in the of direct evidence as transaction. See Part ante. response judgment that, to his motion for argues The Government because Nis- acquittal pursuant to Federal Rule of senbaum was also aware that the IRS was A III: 516 Criminal Procedure See conducting depositions ongo- related to the (Nissenbaum ... “[a]dmittedly doesn’t shelter, ing audit of the Add-On it was have the same involvement that Mr. Co- reasonably foreseeable to him that a co- plan Vaughn and Mr. and Mr. conspirator would commit tax evasion. do”). not, course, The Government does as- proposition sert the that the mere fact of Instead, the Government’s ongoing inquiry suggests, IRS much theory principal liability evasion shows, less criminal knowledge intent or *24 Nissenbaum was based on Pinkerton v. subject inquiry of the is unlawful. States, 640, 1180, 328 66 United U.S. S.Ct. (1946). Pinkerton, 90 L.Ed. 1489 Under The trouble with the Government’s ar- established, conspiracy a has been “[o]nce gument is that “even liability Pinkerton liability the criminal of its members ex ... premised is on a mental state.” Unit- to all wrongdoing occurring tends acts of 260, ed v. Ferguson, States 676 F.3d 279 n. during the of in course and furtherance of (2d Cir.2011) Pinkerton, 18 (citing 328 U.S. conspiracy.” v. United States Gallera (“The 647, at 66 S.Ct. 1180 criminal intent ni, 611, (2d Cir.1995) (internal 68 F.3d 620 to do the act is by established the forma- omitted). quotation marks Pinkerton is words, conspiracy.”)). tion of the In other principle liability not “a broad of vicarious although may permit Pinkerton a broader imposes responsibility upon criminal scope liability of coconspir- for established every co-conspirator for whatever substan ators, the doctrine does not dilute or erode any tive of their offenses confederates requirement the basic person “the Bruno, commit.” United States v. 383 charged with conspiracy knew of the exis- (2d Cir.2004) 65, F.3d 90 (quotation marks tence of the scheme in alleged the indict- omitted). Instead, provides Pinkerton knowingly joined partici- and ment that “a defendant who directly does not pated in it.” Rodriguez, 392 F.3d at 545 may commit a substantive offense never- added) (emphasis (quotation marks omit- be if theless liable the commission of the ted). only The attempt Government’s offense a co-conspirator furtherance identify an affirmative act Nissenbaum conspiracy reasonably of the was foresee- requisite that would demonstrate the crim- able consequence to the defendant as a inal intent is the three-line March 2000 e- their criminal agreement.” United States mail. That simply enough. is Parkes, (2d Cir.2007) 220, v. 497 F.3d omitted). (quotation marks Objective c. False Statements The argues Government that Nissenb- II.A.1.C, noted, aum guilty liability previously was under a Pinkerton As see Part ante, theory it reasonably objective because was foresee- the false statements § able that a coconspirator conspiracy clearly would commit tax directed to noted, evasion. previously charged As the trial the conduct Six and Counts Nissenbaum) defendants (including con- Seven. The Government does not contend they cede that were aware of Add-On’s that Nissenbaum was aware of or involved profit potential February during lack of in the false statements to the IRS as of exchange when an e-mail the Coplan Vaughn depositions. revealed impact profitability separate of fees on the of There was no substantive false on support their convictions in dence against Nissenbaum charge statements Three, charged all which Counts Two deposition. own connection with his with tax evasion the trial defendants Conspiracy a Whole” “As d. prove § 7201. To violation of 26 U.S.C. must § the Government violation of against the evidence Having examined (1) a beyond a reasonable doubt to each of establish respect with Nissenbaum (2) willfulness, deficiency; conspiracy § objectives three substantial One, violation of a again we turn the intentional charged meaning in Count affirmative conspiracy] duty; “looking legal the task of at known [the Co., or defeat a whole.” 370 U.S. “with the intent to evade Cont’l Ore act review of again, 1404. Once our it.” States v. payment 82 S.Ct. tax or (2d Romano, of counsel arguments the record and the Cir. 938 F.2d 1991). the evidence already the conclusion that reviewed the evi compels We have sup liability insufficient against Nissenbaum is the tax evasion supporting dence One. Viewed in con port his conviction Count and Nissenbaum of both the Govern most favorable to light foregoing nection discussion with ment, to Nis respect objective. conspiracy evidence the tax evasion See *25 nearly equal ILAl.b, II.A.2.b, “gives senbaum’s intent ante. For substan Part theory to a equal support compel circumstantial that reversal as tially the reasons theory One,28 innocence.” United guilt and a we that the con to Count conclude (2d Glenn, 70 Cir. v. 312 F.3d Nissenbaum on Shapiro States victions of omitted). 2002) (internal quotation marks Two and Three must be reversed.29 Counts circumstances, “a reasonable these Under a reason

jury necessarily must entertain Sufficiency of the Evidence C. marks omit (quotation able doubt.” Id. Supporting Four Count ted). that Accordingly, we conclude Nis the suf- Finally, challenges conviction on One must Nissenbaum senbaum’s Count Four, ficiency of the evidence on Count be reversed. of the charged which him with obstruction Sufficiency Evidence B. 7212(a). § 26 IRS in violation of U.S.C. Supporting Two Counts 7212(a) noted, prohibits § previously As . and Three “corruptly conduct which a defendant ... ob- by force or threats of force Shapiro and Nissenbaum or Defendants to ob- impedes, of the evi- structs or or endeavors challenge sufficiency also challenges highly fact-specific dissenting Judge sufficiency are partial opinion, 28. In her suggests Shapiro and Nissenb- inquiries require Kearse examination of a careful 2 and 3 See, aum could be convicted on Counts e.g., Ospina v. Trans World the record. because, disagree We under Pinkerton. Airlines, Inc., (2d 1992) Cir. 975 F.2d 37 above, evidence noted there is insufficient ("[Tjhis plaintiffs case turns on whether intro “knew of the or Nissenbaum jury's support the evidence to duced sufficient alleged indict- in the existence of scheme necessarily fact-specific inqui verdict ... a knowingly joined participated ment and above, our close ry.”). For the reasons stated (quotation Rodriguez, in it.” 392 F.3d 545 to the conclu review of the record leads us omitted). marks presented at trial fell that "the evidence sion short’; considerably but more than ‘a trifle dissent, Judge partial Kearse reach- 29. In her is insufficient.” United even a trifle short regard opposite conclusion with to es 1995) Muniz, (2d v. F.3d Cir. States Shapiro’s and Nissenbaum’s convictions J., (Kearse, dissenting). response, simply we note that Counts 1-3. impede, struct or the due administration was that “the Tradehill transaction was internal revenue 26 U.S.C. fully hedge [the code].” intended partners’ expo- 7212(a) 7212(a). key § “The words in [§] sure to fluctuation the euro.” The Re- ” ‘corruptly’ are and ‘endeavors.’ United dacted Indictment alleged that this state- (2d v. Kelly, States F.3d Cir. ment was false “in reality, because 1998). The District Court instructed the transaction had no capacity to do so.” AI: jury as follows: corruptly To act means to act with the The statement at appeared issue in re- advantage intent to secure an unlawful sponse to the first question in the IDR or benefit either for oneself or for anoth- questionnaire: your “Describe all of rea- Acting corruptly requires er. conscious- objectives sons entering into the and/or wrongdoing. ness of Transaction. For each reason ob- and/or A Although VI: we have 428/6193-94. jective, were these objec- reasons and/or previously declined read willfulness letter, tives response achieved?” The IDR 7212(a), § requirement into we have held which was submitted signed by Pros- substantially jury that a similar instruction (“Proskauer”) kauer Rose LLP attorney comprehensive

was “as and accurate as if (“Gutwein”), Abraham Gutwein included a ‘willfully’ the word incorporated ten-paragraph answer to question one. Kelly, statute.” 147 F.3d at 177. Among paragraphs, those ten the Govern- Here, the Government argues Nis- ment primarily quarrels with the following 7212(a) § senbaum violated by causing passage: misleading false and statements to be sub- Partly in order hedge exposure his in response mitted IRS to an IRS *26 the euro and to offset the losses sus- (“IDR”) Request Information Document tained to date with respect Cap to his regarding the Tradehill tax shelter. The Gemini holdings, taxpayer entered with respect prin- evidence to Count Four option into the transactions Novem- cipally implications turns on the ber testimony E partners of two & Y who the currency option positions Under transaction, participated in the Tradehill sold, purchased and the taxpayer would Flashner, Jacob Blank and Martin potential stand the profit substantial who pursuant immunity testified trial to if the euro to in continued decline value originally alleged orders. Count Four (as relative to the dollar had been the the IDR contained four false statements: trend) prevailing option at the exercise motivation. The first alleg- Profit dates.... In that taxpayer manner the edly false statement IDR response fully hedge exposure intended to his partners

was that the E & Y had entered fluctuation the value of the euro. into the Tradehill transaction in order to SA 812. generate profits. After Nissenbaum’s counsel made a Rule 29 motion on Count argues The Government that the direct Four, the Government agreed to withdraw Flashner, examination of Blank and allegation this statement was principal respect witnesses with to Count misleading” “false and and to redact the Four, conclusively they established that Indictment accordingly. did not enter the Tradehill transaction exposure. alleged- hedge against Euro The second exposure order to the

ly response, false statement in the IDR disagree. testimony, euro. We Blank’s Indictment, example summarized the Redacted for both on cross-examination and Q. asking you your primary I’m examination showed that his tax- not redirect objective, asking you purpose only was not the ob- sir. I’m [whether] minimization objective entering into jective the Tradehill On th[e] transaction. examination, Blank testified as fol- transaction was to hedge direct [Tradehill] currency? objective. lows: An THE no. you Yes or Can COURT. enter into transaction Q: you Did answer it? hedge your exposure in order Q. euro? At that time. time, yes. A. At that No,

A: I did not. Q. you did not question The ask [IDR] Q: your purpose then was it not Why was, your objective what it? primary did the euro? hedge A. That is correct. purpose entering A: The into really to generate was transaction Q. objectives that par- So the three the real ... I That was reason

loss. against ticipants hedge had were to my that for- made investment. fact money, make currency, were to and the used, currency options were there eign obvious, why every- tax motive. That’s ... certainly it exposure, was an this, correct, body is is that doing sir? competing factor or a factor that we on, foreign to focus ... were able but

currency exposure was the reason A. Yes. into the deal. we entered The reason Id. at And on redirect exam- 609/3121-23. the tax loss. get was to ination, harked the Government back to

Blank’s testimony Cap that because the Gemini stock he had received “was not What, Q: any, you if understanding did rather denominated in dollars” but “was have at the time of the transaction about foreign currency, in a ... denominated hedge much of a how this transaction justification entering into the transac- provide? could *27 from perspective tion a business was to be A: I had none. to, effect, try able to hedge in reduce What, any, Q: you if did discussions owning the risk associated with non-U.S. have with other members of the transac- dollar denominated investments.” Id. at how much of a this hedge tion about sought It clarification: 570/2966-67. provide? transaction could Q. you On direct examination said that A: None. hedging justification the euro was a for you the Do transaction. remember us- Q: response] In that says: This [IDR that ing word? taxpayer fully manner the intended to Yes, sir, A. I do. hedge exposure his fluctuation in the Q. you mean that? What did euro, is that

value of the statement true? A. At the time we entered into correct. A: It’s not transaction, assuring I was desirous of purpose A But on II: cross examina- there was a business for 588/3037-38. tion, transaction, at that time I equivocated acknowledging Blank did currency exposure, in have hedging against foreign fluctuations be- cause, that we objective,” again, euro was “an follows: the stock were foreign in the sale was not denom- investment. The fact that curren- awarded dollars, used, cur- foreign cy options inated in it was were there was exposure ... rency, certainly and to the extent that trans- it was a or a compet- factor offered, on, we entered to the best of ing action factor that we were able to focus time, my knowledge possibili- at the but ... foreign currency exposure was not ty trying mitigate hedge or some we reason entered into the deal.” A going with the dollar the risk associated II: straightforward impli- The 588/3037. down, that to me up going dollar cation of testimony hedging Blank’s is that time, at that based what I understood on against fluctuations the euro was not the then, represented purpose a business for primary entering reason for the Tradehill entering into transaction. this transaction. But that was question not the Q. you posed by Question it the entered into the IDR. Was reason number one “[djescribe prompted taxpayer the transaction? all of your reasons objectives entering primary A. It was not the reason. and/or the Transaction.” Blank’s statement —in Id. at 618/3156. excerpted by the same sentence the Gov- The record reflects a similar tension foreign currency exposure ernment —that Flashner, respect who testified on “certainly appears factor” consistent direct examination that he did not enter with the statement in the IDR response hedge the Tradehill transaction in order to “[pjartly the transaction was entered euro, 24/3395, A III: exposure his in order to hedge.” (emphasis SA 812 but examination that the admitted cross added). E & Y partners “exchange discussed (S) understandings. Non-written presented by receipt rate risk” their allegedly third IDR false statement euros, stock denominated in id. at 32/3424. “[tjhere response was that were ho non- Flashner further testified that “it would understandings” partic- written among protect “by make sense” to his investment ipants in the Tradehill transaction. The trying money to make some from this alleged Redacted Indictment this against downward movement of the euro reality, statement was false because “in Finally, the dollar.” Id. at 33/3430-31. understanding among there was an all the goals Flashner admitted that his in invest- parties to the that the E & Y transaction ing Tradehill were “two-fold”: to obtain partners option positions would exit their profit losses and “to earn a from the before the end of in order to claim transaction.” Id. at 24/3394. ... they tax losses could use to offset their Faced with obvious internal tension AI: income.” testimony principal within the of its two *28 Four, testimony witnesses on no Count the Government There was affirmative jury rely that “the the avers was entitled to on about existence of “non-written under- the direct examination.” Gov’t’s Br. 185- standings” among partici- the Tradehill fact, jury fully pants. 86. But even if the credited the In both Blank and Flashner examination, in engaging any direct as we must assume denied discussions with here, testimony E & Y their implicit support partner exiting lends other about 578/2997,579/3000, A option positions. Nissenbaum’s defense as well. As not- II: (Flash- above, (Blank); A testimony ed Blank’s direct was III: 580/3005 23/3389 ner). Nevertheless, purpose entering into the the Government in- “[t]he really generate transaction was the loss. that the “entire thrust” of their sists testi- my mony partners entering That was the real ... I was that the were reason made testify any expec- Flashner did not a tax generate Tradehill transaction to the would take future business to year, the or referral of loss for same tation any affirma- necessary to that end. In the absence steps the Proskauer. only “specu- left with the proof, tive we are that the Gov- assuming arguendo Even expecta- lation and surmise” that such the “thrust” of ernment is correct about Smith, 630 F.3d Langston v. tion existed. a more fundamental defect testimony, the (“[A] (2d Cir.2011) conviction the Tradehill in remains: allegation this and surmise alone speculation based on retained Gutwein—not Nis- participants ” omit- marks (quotation cannot stand.... regard represent them senbaum—to ted)). Gutwein, pow- who had to the IRS audit. partici- attorney from the Tradehill ers of the record and Having reviewed substantially response pants, revised counsel, conclude that arguments of we the “under- proposed that Nissenbaum about of Nissenb- compels the record reversal E & Y standings” among partners. the Four. Given aum’s conviction on Count response, IDR Nissenbaum noted a draft testimony by Blank and equivocal the ‘understandings’ involved the “[a]ny and the role of Gutwein draft Flashner options, and contribution of purchase jury IDR “a reasonable ing response, the creation of the various entities and necessarily entertain reasonable must generated the loss- sale of the assets corrupt as to whether Nissenbaum doubt” A 130. Gutwein then revised the es.” V: Glenn, IRS. ly impeded obstructed or were no response to state that “[t]here omitted).30 (quotation F.3d at 70 marks understandings between the non-written Thus, appears it participants].” [Tradehill Six, Propriety for Count III. of Venue language suggested by that the Nissenb- Charging Vaughn with False the language aum was more accurate than IRS Statements IDR response. of the final challenges pro- Vaughn Defendant (Jf) The fi- Future business. referral Six, charging of venue for priety Count IDR allegedly nal false statement in the making him with false statements expecta- was that there was no response during deposition IRS a June any tion referral of future business to or Nashville, Tennessee, in violation of 18 Proskauer, reality, “when in § U.S.C. clients to [Pros- defendants referred PICO letters.” The Govern- opinion kauer] Legal A. Standard on the fact that about the time ment relies in criminal “[p]roper pro Because venue legal opin- completing Proskauer was ceedings was a matter of concern to shelter, given for the Tradehill it was ions founders,” States Nation’s the United Con opinions, paid writing work of PICO safeguards “twice defendant’s stitution prepared by which to that been point had Cabrales, right.” venue States v. timing, Arnold & Porter. Based on the 1772, 141 1, 6, 118 L.Ed.2d 1 524 U.S. S.Ct. argues jury that the the Government (1998). requires Article III that “the Trial conclude that there was indeed an free to ... State all shall be held of future busi- of Crimes “expectation referral” *29 have been ness, where the said shall rendering the IDR Crimes statement Const, 2, Ill, § art. cl. But Blank committed.” U.S. contrary misleading. false and Judge Four on sufficien- underscoring the fact that aum's conviction on Count 30. It bears cy grounds. agrees of Nissenb- Kearse with our reversal

77 (2d 202, Cir.2010) (internal provides 3. The Sixth Amendment further F.3d 205 quota- omitted). all criminal the ac- prosecutions, tion “[i]n marks alterations Con- enjoy right speedy cused shall to a gress has codified the so-called “continuing trial, public impartial jury of the offense” 3237(a), § rule in 18 U.S.C. which State and district wherein the crime shall provides in part: relevant VI;31 have been committed.” Id. amend Except as expressly otherwise provided (requiring see also Fed.R.Crim.P. 18 by enactment Congress, any offense government prosecute “the must an of- against the United States begun one fense in a district where the offense was another, district and completed or committed”). district, committed more than one may be ... prosecuted any district in When relevant federal statute which such offense was begun, contin- specify does not how to determine the ued, or completed. “committed,” location where the crime was The Government bears locus delicti must “[t]he determined be. burden of proving that venue is proper. alleged from the nature the crime Tzolov, 642 F.3d at 318. venue “[T]he the location constituting of the act or acts requirement, despite ped its constitutional Cabrales, 6-7, it.” 524 at 118 U.S. S.Ct. igree, is not an element of a crime so as to 1772. In conducting inquiry, this we require proof beyond doubt; a reasonable initially “must identify the conduct consti rather, venue proved only need be by a ... tuting the offense and then discern the preponderance of the evidence.” United location of the commission of the criminal 108, (2d Rommy, States v. 506 F.3d 119 acts.” United v. Rodriguez-More States Cir.2007) (emphasis and internal quotation no, 275, 279, 1239, 526 U.S. 119 S.Ct. 143 omitted). marks The propriety of venue is (1999). proper only L.Ed.2d 388 “Venue is a question of law that we review de novo. where the constituting acts the offense— United States v. Drachenberg, 623 F.3d the crime’s ‘essential conduct elements’— (2d 122, 124 Cir.2010). Tzolov, place.” took United States v. (2d Cir.2011)

F.3d (quoting Rodri statute, The federal false statements guez-Moreno, 526 U.S. 119 S.Ct. 1001(a), § crime, U.S.C. makes it a inter 1239). alia, “in any jurisdiction matter within the executive, legislative, judicial or “When a crime consists of a sin branch of the Government of the United act, gle, non-continuing proper venue States, knowingly ... willfully [to] is clear: The crime is ‘committed’ in the false, fictitious, any materially make[ ] performed.” district where the act is fraudulent statement or representation.” Ramirez, United States v. 420 F.3d 1001(a)(2). § 18 U.S.C. (2d (other Cir.2005) quotation internal omitted). cases, marks In other “where We have considered the issue of 1001(a) constituting § acts the crime and the pri- venue violation on two nature of the crime charged implicate or occasions. In United States v. Candel location, la, (2d Cir.1973), more than one the Constitution 487 F.2d 1223 a case does not a single arising command exclusive ven in the Southern District of New York, ue.” v. Magassouba, United States charged the defendants were "Technically, specifies practical Article III importance.” Roy ‘venue’ United States v. er, specifies ‘vicinage,’ and the Sixth Amendment (2d Cir.2008). 549 F.3d 893 n. 8 longer but that refined distinction is no *30 78 for in Manhattan afforded no basis fraudu- officials based on

making false statements of New in the Southern District to a venue affidavits that were submitted lent disagree. and York. We Brooklyn municipal branch office Housing the and Urban conveyed then begin by identifying the “es We in Manhattan. Id. at Development office 1001(a)(2). § elements” of sential conduct that, crime although the 1227. We held 280, at 119 526 U.S. Rodriguez-Moreno, District of New in the Eastern began Ali, v. 1239. In States S.Ct. United York, that the crime “it does not follow (2d Cir.1995), amended on deni F.3d 1468 terminated, transpired that what then (2d Cir.1996), we reh’g, 86 F.3d 275 al of irrelevant for venue in Manhattan was materiality is a for the first time that held at 1228. In States purposes.” Id. United under statutory charges element of all (2d Ramirez, Cir.2005), we 420 F.3d 134 v. Ali, 1474-75; F.3d at see § 1001. Candella, reasoning of upon elaborated the 519, Mandanici, States v. 205 F.3d United that, where a false statement was holding Cir.2000). (2d Thus, order to se then trans- jurisdiction in one made 1001(a)(2), § the a conviction under cure another, proper mitted to venue was prove must that a defendant Government (holding jurisdictions. Id. both (1) (2) willfully, made a knowingly in the District proper venue was Southern false, fictitious, fraudulent materially or New York because the “‘statements of statement, in relation to a matter with to be to be false and continued continued jurisdiction department of a or in the the States’ jurisdiction in the of United States, with agency finally reached Manhattan” they when or fictitious or knowledge that it was false 1228)).32 Candella, 487 F.2d at (quoting fraudulent.33 B. for Count Six Venue statutory not all elements But conduct elements” for constitute “essential Vaughn contends that venue Count meaning Rodriguez-Moreno. his statements within improper Six was because § the elements of during reviewing In were both made and received Supreme has noted that statuto in Nashville. For that rea- Court deposition IRS the false statement be son, subsequent ry requirement re- Vaughn argues, any jurisdic- matter within the by IRS made “in analysis view and of his statements mentioning materiality distinguish element. Vaughn Candella and without 32. seeks to See, Wiener, involved written e.g., because both cases v. 96 F.3d United States Ramirez 1001(a)(3), § in violation of (2d Cir.1996) ("To false statements a defendant of convict in violation rather than oral false statements government violating must Section end, 1001(a)(2). Vaughn § con- To that (i) knowingly and prove that the defendant: 1001(a)(3), prohibits § the text of which trasts statement, (iii) (ii) willfully, made a in relation " "mak[ing] us[ing] of a written false jurisdiction depart- to a matter within'the statement, 1001(a)(2), § with the text of States, (iv) agency ment or of the United "mak[ing]” prohibits only the of an which knowledge that it was false or fictitious Ra- statement. But Candella and oral false fraudulent.”). holding light explicit of our rely upon subsequent "use” did not mirez "materiality is indeed an element of to find that of the false statements order offense,” Ali, subsequent 68 F.3d at our Moreover, properly laid. we find venue was materiality incorporate into our failure to 1001(a) § in the text of no indication statutory elements standard recitation of (a)(2) differently is be treated subsection simple appears § 1001 to be the result of (a)(3) purposes of venue. than subsection oversight. Ali, occasionally we have stated Since charge § elements of a 1001 false statements

79 “jurisdic- requires ... the States” is evidence that those tion of statements phrase in a language appears conveyed tional were to or an [that] had effect on the prohibited conduct” and separate investigators working from IRS in the Southern “predicate circumstance” simply is District of New York. Oceanpro, 674 F.3d Yermian, States v. 468 329; Salinas, offense. United at v. see United States 373 2936, 63, 68-69, (1st Cir.2004) (“When 104 82 L.Ed.2d 161, U.S. S.Ct. F.3d 167 mate- omitted). marks Sim- (quotation 53 riality component is a critical of the statu- requirement consti- ilarly, the mens rea definition, tory it perfect makes sense to “a element that tutes circumstance does consider the crime continuing as into the determining not contribute to the locus in district which the effects of the false delicti of the crime.” United States v. felt.”); statement are v. United States Indus., Ltd., 323, Oceanpro (7th Cir.2002) 674 F.3d 329 788, Ringer, 300 F.3d 792 (4th Cir.2012).34 Thus, the essential con- (finding venue the district where the 1001(a)(2) § prohibited by duct is the mak- investigation “reasonably likely was to be fictitious, false, ing materially of a statements”). affected [the defendant’s] fraudulent statement. Smith, But see v. United States 641 F.3d (10th Cir.2011) 1200, venue, 1208 (finding case, materiality In re this recorded, where false statement was not quirement proves dispositive respect only in jurisdiction where the false 1001, § to venue. a statement is “Under made). statement was We therefore con- tendency material if it has a natural clude that venue for Six proper Count was influence, capable influencing, or be in the Southern District of New York.35 decisionmaking body decision of the addressed, capable which it was or if it is fully This result is consistent with our distracting government investigators’ holdings Candella and Ramirez. It is away attention from a critical matter.” undisputed Vaughn the false “ma[de]” Adekanbi, 178, United States v. 675 F.3d during deposi- statements issue the IRS (2d Cir.2012) (internal citations, quota 182 tion in Nashville—but “it does not follow omitted). marks, tion and alterations Ac terminated, that the crime then and that cordingly, Vaughn’s whether false state transpired what in Manhattan was irrele- tendency ments were material turns on the Candella, purposes.” vant for venue 487 or capacity of those statements to influ Ramirez, F.2d at 1228. offense decisionmaking body ence the at issue—in began Jersey, New where the fraudu- case, this the IRS. filed, paperwork lent was and ended in the York, materiality Proving Vaughn’s juris- Southern District of New necessarily Jersey false statements Tennessee diction to which New officials for- (4th Cir.2000) Clenney, (holding language 34. United States v. 434 F.3d "de- Cf. (5th Cir.2005) (holding 782 the intent fin[ing] requisite intent for the offense” of statute, parental kidnapping element harboring fugitive, § 18 U.S.C. was § "merely speaks U.S.C. to the offend- element). not an essential conduct rea er's mens as he commits conduct crime; plainly essential it is Vaughn similarly argues grand required by element’ 'essential conduct jury jurisdiction lacked to return Count 6 of Ramirez, Rodríguez-Moreno"); F.3d at Superseding the of- Indictment because ("While certainly a scheme to defraud is outside the district fense was committed fraud, one of three essential elements of mail element____ impaneled. jury where the This chal- it is not an essential conduct It lenge substantially fraud.”); the same reasons fails for is the mens rea element of mail Bowens, III.B, challenge. United States v. 224 F.3d as his venue See Part ante. *32 Ramirez, Magassouba, trial.” States v. 420 his United paperwork. warded the (2d Cir.2010). 202, 2 of- 205 n. We Similarly, the instant 619 F.3d F.3d at 137-38. Tennessee, pro- where in this case the District Court began fense case think care consider- required statements to IRS with the made the false ceeded Vaughn officials, Reed and ing into the Southern the factors enumerated but continued York, deposition concluding that “the sub- of New where his Saavedra before District weighs in favor analysis reviewed and discussed contacts transcript was stantial ongo- Vaughn in connection with the does not IRS officials of venue this district.” of that Vaughn’s challenge fact that the substance ing appear E & Y audit. The “ appeal. to be false and ‘continued determination statements the jurisdiction in the of continued to be of Graham IV. Admission finally reached they States when

United ” Taylor Testimony Candella, Manhattan,’ (quoting at 143 Id. 1228), our view that at confirms 487 F.2d validity, to their suffi In addition District proper venue in the Southern was ciency, jurisdictional challenges, and of New York. variety mount a of trial defendants also occasion, supplemented our On we have In first of evidentiary challenges. a contacts” inquiry these, venue with “substantial they argue that the District Court into account a number of testimony test that “takes of Gra admitting erred in acts, the defendant’s attorney factors —the site of who worked at Taylor, ham a tax crime, nature of the the elements and who Pillsbury the law firm of Madison and conduct, the effect of the criminal variety locus of a of crimes indisputably committed for accu- suitability and the of each district unrelated to this involving tax shelters Reed, v. factfinding.” rate States United rul case. We review the District Court’s Cir.1985). (2d 477, Since admissibility 773 F.2d 481 of evi ings regarding Reed, ig- alternately applied we have of discretion. dence at trial for abuse Williams, 703, the substantial contacts test. Com- nored States v. 585 F.3d United 886, Royer, (2d Sims, v. 549 F.3d pare Cir.2009); United States In re 534 F.3d cf. (2d Cir.2008) approv- (2d Cir.2008) (citing Reed that the (explaining al); Saavedra, 223 F.3d States v. includes term of art “abuse of discretion” Cir.2000) (2d (same); law). with Unit- 92-93 errors (2d Tzolov, ed States v. 642 F.3d of discus- Taylor had series Cir.2011) to a ‘sub- (“Though Reed refers with E & about the CDS transaction sions determining contacts rule’ for ven- stantial Smith, partner Y David the defendant regarded ue ... it is clear that the [court] at the time fugitive this action who was a the defendant’s acts as locale of Taylor opinion drafted an initial of trial. (al- venue.” establishing sufficient basis for transaction, regarding letter CDS (other quota- internal original) teration in eventually the transaction brought Smith omitted)). tion marks E Y. opinion letter to & and the draft held, letter contained a Taylor’s opinion we draft previously We have variety regarding of statements CDS clarify, now that use of the substantial false, where, in- that he knew were may appropriate be transaction contacts test (1) purpose here, cluding statements that “argue[s] the defendant his profit; ... partnership in the was investment prosecution district] [contested risk; him, money have the investors would hardship preju in a [will] ] result! swap him, early termination the fairness undermine[ ] ] dice! 104(b). predetermined. Taylor testified introduced later.” Fed.R.Evid. agreed he and Smith had that these faced with a question When conditional relevance, elements of the transaction could not core district court should “exam- disclosed in letter if the all the opinion ine[ ] be evidence in the case and de- yield the intended tax jury cide!] transaction were to whether the could reasonably *33 a phone by Other than brief call find the ... benefits. conditional fact a prepon- & Y employees with two unknown E derance the evidence.” Huddleston v. 1999, States, 681, Taylor no contact with June had United 485 U.S. 108 S.Ct. anyone (1988). E Y ultimately else at E & Y. & case, L.Ed.2d 771 In this engaged Brent at Locke Clifton Liddell the defendants the argue that relevance of Taylor Taylor’s rather than write the opin- testimony upon to CDS depended pre- a letter. liminary ion “conditional fact”—that the con- versations between Taylor and Smith were Tay- The to exclude defendants moved ultimately conveyed to the defendants. trial, testimony prior arguing lor’s that Taylor the absence of that evidence had testimony primarily his would consist anyone substantive with conversations else recounting his with Smith. conversations Y, E & or anyone at that Smith told Eat that, argued The defendants since there Y about Taylor, & his conversations with no evidence that the substance of argue the defendants that the Government relayed been those conversations had carry failed to prove its burden to the defendants, Taylor’s testimony was not the by conditional fact a preponderance. relevant. The Government conceded that produce it would not direct “evidence that Despite the appar Government’s Taylor directly anyone with communicated 104(b) ent failure to the Rule confront E & Y falsely what was stat- regarding analysis appeal, persuaded arewe that in, from, or intentionally ed omitted his Taylor’s testimony was admissible as di opinion,” argued that a jury draft but conspiracy. rect evidence of the a pre As could infer that matters necessarily “those matter, liminary we note that the draft conveyed by would have been Smith to one opinion by Taylor letter prepared and the or more of the The District defendants.” opinion by final letter Locke issued Liddell denied the defendants’ motion Court similar, substantially were and that some allowed the to present Tay- Government passages appeared copied nearly to be ver testimony, warning lor’s while that the Indeed, the batim. even defendants ac required Government would be to “connect knowledge certainly that “it was reason up” evidence. able to conclude that Locke Liddell had letter, copy Taylor’s received a and that appeal, princi On defendants it had as a starting point used letter argue admitting Taylor’s pally tes Thus, Taylor’s for its own.” testimony timony, the District Court misunderstood opinion about content of the draft let obligations its under Federal Rule of Evi independently ter was admissible as to 104(b), questions dence which governs manifesting the circumstances formation of 104(b) Rule pro conditional relevance. conspiracy. vides the relevance of evi “[w]hen exists, depends Taylor’s a fact testimony dence on whether about his conversa- proof admittedly presents must be sufficient sup introduced tions Smith finding fact port question does exist. closer of conditional relevance. may proposed Taylor court length admit evi testified at about the various proof dence on the that the be facts about the condition CDS transaction had Alameh, v. States spiracy.” opinion the tax be omitted from Cir.2003) (2d (quotation As the misleading terms. F.3d described omitted). notes, about striking “preliminary “what is These are marks Government they precisely are is that Taylor’s concerns to be resolved questions of fact” defendants, in e that the same facts preponderance court under a district e-mail, against people cautioned mail after Bourjaily v. United evidence standard. these Based on revealing to the IRS.” 171, 175, States, 107 S.Ct. 483 U.S. similarities, concluded District Court (1987). 97 L.Ed.2d 144 infer that jury could that a reasonable on to passed concerns were

Taylor’s error a dis review for clear We present circumstances In the defendants. to whether “there findings trict court’s *34 here, Although the defen agree. we ed the declarant conspiracy involving awas there is no evidence protest that dants nonoffering party, and [whether] and the the de directly with Taylor communicated the course during was made the statement fendants, a state required have never we conspiracy.” the and in furtherance of member to each ment to be disseminated Embassies Bombings Terrorist U.S. re to be admissible conspiracy the order (2d Cir.2008) 93, 137 Africa, in E. 552 F.3d States v. the whole. United against Cf. omitted) (alteration in marks (quotation (2d Cir.1988) Friedman, 535, 562 854 F.2d noted, we review original). previously As (“[Tjhere that each requirement is no the as to a district court’s determination conspire directly conspiracy of a member admissibility of evidence at trial for abuse conspira the other member of every with Williams, at 707. 585 F.3d of discretion. we affirm the District cy.”). Accordingly, trial, identified Prior to the Government Taylor’s testimo decision to admit Court’s with the defen- people coconspirators 50 as ny- dants, figures central such as including Coconspirator Admission of Smith, V. Belle Cinquegrani, Peter David Statements offered out-of- Six. When the Government alleged coconspira- court statements of the argu in an Vaughn, Defendant trial, that the objected the tors at defense the trial defen joined by ment each of had not carried its burden Government dants, com that the District Court argues excep- coconspirator elements of the by admitting error mitted reversible the evi- The District Court admitted tion. 20 of more than out-of-court statements pro- subject to connection under dence Federal Rule of alleged coconspirators. Bourjaily v. United cedure established is provides 801 that a statement Evidence States, 171, 107 S.Ct. 97 483 U.S. a hearsay against if it both offered is (1987), permits 144 which dis- L.Ed.2d by party’s cocon- and is “made party hearsay to “examine the state- trict court in furtherance of the spirator during and “making a sought ments to be admitted” 801(d)(2)(E). conspiracy.” Fed.R.Evid. Id. at preliminary factual determination.” testimony Rule hearsay To under admit 2775. At the close of 107 S.Ct. 801(d)(2)(E), court “must find the district case, filed a mo- (b) Government’s the defense (a) conspiracy, a that its that there was the out-of-court statements tion to strike the declarant and the members included After hold- coconspirators. alleged of whom the statement is party against (c) re- (the ], on the motion and ing argument oral party”) “nonoffering fered [ for addi- copies of certain exhibits during questing that the statement was made review, a made tional the District Court in furtherance of the con- course of and

83 ruling prerequisites ruling. blanket that “the of of the District Court’s Vaughn See 801(d)(2)(E) (“In fact, Rule have been shown a Reply point of it is the sum mary of the evidence with re- preponderance fashion which the District Court spect conditionally detailed, to each of the admitted dispensed with these specific ob jections by statements.” the Defendants which forms of Vaughn’s argument concerning basis argue appeal The defendants that the point this on appeal.”). Although the blan District blanket admission of the Court’s ruling by ket certainly District Court coconspirator transgresses statements difficult, appellate makes review more we Rule proper use of “limit[s] [on] have never required district court to 801(d)(2)(E) coconspirator to admit testi- particularized make rulings or conduct mony.” Gigante, States v. separable analyses respect to each (2d Cir.1999). Specifically, F.3d coconspirator, coconspira much less each that, Vaughn argues as to most or all of tor statement. United States v. Al Cf. alleged coconspirators, the Govern- (2d Cir.2008) Moayad, 545 F.3d prove they ment failed to had (vacating the judgment because “[t]he join intent to further an illegal ven- court findings, by preponder made no (“It ture. unity See id. is the *35 otherwise, ance of the evidence or about stemming specific interests from a shared conspiracy” (emphasis the existence of a justifies criminal task that Rule added)). The record makes clear that the 801(d)(2)(E) in place....”). the first For experienced judge able and district re example, argue the defendants two papers, viewed the defendants’ motion held accountants, outside Fred Goldman and argument, oral obtained additional evi Cooper, “merely Robert were outside func- Government, dence from the applied tionaries” and “cannot be considered ‘co- standard, legal correct and a consid made conspirators’ with the defendants under facts, ruling. light ered oral In of these any definition of reasonable the term.” clearly the District did not err in its Court response, the Government accuses factual determination that the out-of-court Vaughn “cherry-pick[ing]” testimony of statements were made in furtherance of argue his case when there “ample conspiracy, and therefore did not Goldman, evidence” to establish Coo- by admitting abuse its discretion the out- per, coconspirators and others were with coconspira of-court statements under In particular, the defendants. the Govern- exception. tor Cooper acknowledged ment notes that given trial that he had false and mislead- Coplan VI. Exclusion of Portions of ing testimony during an IRS tax audit and Vaughn Deposition and helping that he believed he was clients Transcripts signed commit tax evasion when he tax that the Dis- Coplan Vaughn argue and for the returns Add-On transaction. by ex- trict Court abused its discretion Upon foregoing cluding portions review of the ar from evidence of their de- guments, appears it an position transcripts. part defendants’ As IRS Y,36 objection fundamental to the exam” of E & the IRS coconspirator “promoter in June generalized deposed Coplan Vaughn evidence relates to the nature both and laws, (as "promoter organizer opposed principal 36. A exam” to an "in- or an under the exam”) underlying come tax to determine and whether transactions aims entity whether under examination is a constitute tax shelters. admissible.”). Here, hearsay, and it is not formed deposition transcripts 2002. The challenge the District Coplan Vaughn and Seven of the the basis for Counts Six ruling that the bulk of predicate Indictment, Court’s charged which Co- Redacted offered for transcripts were deposition making false state- Vaughn plan But as trial, the truth of the matter asserted. the Govern- to the IRS. At ments concedes, tacitly see the Government only portions sought to introduce ment by the questions posed Br. Gov’t’s containing deposition transcripts hearsay, because as a agent IRS were not Six alleged in Counts the false statements law, questions are “asser- matter Vaughn sought to Coplan and Seven. meaning of Rule see tions” within the transcripts in deposition their entire admit F.2d statements, Oguns, States v. that the order to demonstrate Cir.1990) (“An (2d inquiry is not ‘asser- false, to the even if were not material tion,’ is not and cannot be accordingly exam. The District Court promoter marks hearsay (quotation statement.” counter-desig- certain accepted thereafter omitted)). Thus, erred defendants, the District Court but proposed by nations rule exclude by invoking hearsay transcripts, to admit the entire refused deposition in the questions contained portions the excluded were holding by transcripts. “largely hearsay offered inadmissible defendants, they simply irrele- [we]re hearsay the defen status of vant to the issues here.” ques a closer responses presents dants’ again,

Once we review district court’s Coplan responses insists that his tion. admissibility determination as the mat were not offered for the truth of evidence at trial for abuse discretion. asserted, “the over ter but to demonstrate *36 Williams, 585 F.3d 707. interview, in all of the the context purpose made, were charged which the statements Alleged

A. The Error fully in willingness cooperate [his] that, in Coplan Vaughn argue ex- Coplan Reply the interview.” n.5. percent depo- Coplaris more than 80 of the true cluding Government counters that, transcripts, jury sition the District Court erred convince the purpose was to (1) deposi- bulk of the ruling lengthy deposition, that the the course of a he was hearsay; transcripts mostly tion constituted truthful. The Government’s con failing to admit the statements under the from support tention finds a letter brief counsel, failing completeness; rule of which made clear that he Coplaris under the state of tran deposition admit statements wished to admit the entire exception hearsay forthcoming mind to the rule. in order to show “his script proceeding.” SA 303. In approach Hearsay facts, light of these the District Court did by invoking not abuse its discretion Federal Rule of Evidence

Under hearsay deposition rule to exclude the re 801, hearsay a statement is an out-of-court sponses. ... prove “assertion” that is “offerfed]

the truth the matter asserted in the Completeness” 2. “Rule of 801(a), (c); statement.” Fed.R.Evid. see Marin, Federal Rule of Evi States v. 669 F.2d Under (2d (“When Cir.1982) all party the defendant seeks where a introduces or dence statement, an adverse part of a recorded prior to introduce his own statement for asserted, any the introduction of party may require truth the matter it is ought “in to be part transcript other fairness tions of the were admissible un- considered at the same time.” Fed. der this “state of mind” exception. particular, R.Evid. 106. The so-called “rule of com Coplan argues that a statement that “even pleteness” provides though evincing his confusion about the definition may hearsay, por be an omitted of a “digital option” statement should have been ad- must be placed tion of statement mitted “to show lack understanding [his] necessary to explain evidence if admit of some of the financial instruments in- portion, place portion ted the admitted Coplan volved.” Br. although 83. But context, 803(3) misleading jury, Coplan to avoid or raised Rule “in general below, fair impartial understanding to ensure appears terms” it that his current portion.” argument of the admitted v. United States certain statements were —that (2d Cir.2009) 141, 144 Kopp, (quo 562 F.3d prove admissible to his lack of technical omitted). not, tation marks The rule “does acumen—was never presented to the Dis- however, (District require the portions admission of trict A III: Court. 218/4167 explanatory statement that are neither ruling noting Court that defendants “ha- of nor relevant to the admitted passages.” given ven’t any specificity of statements omitted). Id. (quotation marks that show state of of Vaughn mind Coplan”). case, Coplan In this and Vaughn

argue that the District Court erred in Prejudice B. concluding portions transcript of the offered under Rule 106 could still be ex event, In any even assuming arguendo hearsay cluded under the Although rule. that the District Court erred not admit- initially the Government misstated the ting entirety deposition tran- below, standard Coplan identified the mis scripts, the error was harmless. Fed. immediately, take almost and there is no 52(a) (defining R.Crim.P. “harmless error” indication that misap District Court error, defect, “[a]ny irregularity, or var- prehended or misapplied the Rule 106 iance that does not affect substantial standard in electing to admit the defen rights”). The argue defendants that the counter-designations dants’ but not the en “gutted” erroneous exclusion their defense *37 transcripts. Citing tire the relevant stan “were, best, that the false statements Jackson, dard from United States v. 180 ancillary investigation.” Coplan to the Br. (2d 55, Cir.1999), F.3d 73 the District record, 85. But the full context of the it Court “[u]sing stated it was [Rule] is clear that ample defendants had polestar” 106 as a filter or a in refusing to opportunity arguments to make these deposition transcripts admit the in their through their cross-examination of the IRS entirety, but a admitting number of coun agent and their closing arguments. More- ter-designations. We find no abuse of dis over, jury testimony heard explaining cretion in that determination. how all of the information sought IRS material promoter was to the exam Exception

3. “State of Mind” subject that was the of the deposition. On 803(3) record, that, Federal Rule of Evidence Rule this we conclude even if the provides hearsay exception for state- exclusion of the deposition testimony “[a] was erroneous, ment of the then-existing declarant’s state the error harmless. was See emotional, Farhane, ... or sensory, phys- 127, mind States v. 634 F.3d United 803(3). (2d Cir.2011) ical condition.” (deeming Fed.R.Evid. 164 harmless defendants contend that por- the excluded exclusion of state of evidence where mind

86 error, prejudicial the level of was marks rise to contrary evidence

Government’s severity of the miscon- we examine ‘the v. overwhelming”); United States “clearly Cir.2006) duct, (2d to cure 137, adopted the measures F.3d 140 Song, 436 misconduct, certainty of conviction the erroneous exclusion (deeming harmless ” States v. the misconduct.’ United absent mind evidence where defendant of state of Cir.2011) (2d 85, Gansman, 657 F.3d 96 testify in de- sufficient permitted “was Caracappa, v. 614 (quoting States United theory of the case” tail as to his Cir.2010)). (2d 30, 41 F.3d overwhelming evi- presented Government guilt). dence of re “surprise” respect With well argument, it is established buttal Alleged Misconduct Prosecutorial VII. provides government “[r]ebuttal Vaughn, joined by Coplan and Shapiro, respond to defendant’s opportunity the Government committed argues that govern It does not allow arguments. by introducing misconduct prosecutorial matters.” bring ment to in new United misrepresenting surprise arguments (2d Giovanelli, 479, 945 F.2d 495 States v. Spe- in its rebuttal summation. evidence omitted). Cir.1991) In (quotation marks (1) the challenge cifically, the defendants context, however, appears it that the “sur “surprise” arguments about Government’s argument briefly IDR prise” PICO IDR; responses client PICO opening in the Government’s discussed description Government’s COBRA galling of the most summation as “one “amazing” and an and “ex- as a “trick” by the examples” prepared of statements of the relevant tax traordinary” distortion falsely described their defendants that regulations.37 The Govern subjective intent. clients’ IDR ar then returned to the PICO ment matter, general a defen As rebuttal, highlighting the fact gument remarks asserting prosecutor’s that a dant counsel had ad “ that none of the defense heavy trial ‘faces a bur warrant a new Re responses. IDR dressed PICO den, alleged the misconduct must because although turning argument to an noted— as to result significant be so severe and the Government its emphasized by ” not — right to a fair trial.’ the denial of his regarded cannot be opening summation Banki, v. 685 F.3d United States Br. and unfair.” “deceitful Cir.2012) (2d v. Lo (quoting United States the context of a rebuttal summation (2d Cir.1993) (alter cascio, 6 F.3d transcript, of trial spanned pages some 120 omitted)); v. see also States ations any here cannot be deemed misconduct (2d Cir.2010) Whitten, 610 F.3d Newton, States v. severe. See United (“We ground prose- will reverse on the (2d Cir.2004) (cautioning F.3d *38 only cutorial misconduct if that misconduct “disproportionate emphasis against [on] by infect prejudice caused substantial so error”). alleged isolated incidents of the the trial with unfairness as to make ing challenge pro The defendants also resulting conviction a denial of due omitted)). (internal description of the the Government’s CO quotation marks cess.” a “trick” and an re- BRA transaction as considering inappropriate “In whether already we have argues BRA transaction. Because Shapiro that the Government's also Shapiro’s conspiracy the rec- convic- rebuttal summation mischaracterized that concluded by telling jury Dougherty had ord the that sufficiency grounds, reversed on tion must be why them that "Mr. lied about "told” argument. we decline to address this corporation for the CO- the S was needed” matter, a “extraordinary” general distortion As we review “amazing” and regulations. relevant tax This ar- a properly preserved claim of error re novo, It is gument equally unpersuasive. is garding jury instructions de revers that the Government where, well established ing only “viewing charge the as a it latitude in the inferences whole, “has broad prejudicial there was a error.” jury may reasonably suggest to the dur- Aina-Marshall, States v. 336 F.3d States v. Ed- ing summation.” United (2d Cir.2003). 167, 170 The trial court Cir.2003) (2d wards, 342 F.3d “enjoys broad discretion in crafting its in omitted). case, (quotation mark In this structions[,] which only is circumscribed ample had evi- presented Government requirement charge that the be fair support dence to the inference that CO- Brand, to both sides.” United States v. that, BRA—a shelter rather than defer- (2d Cir.2006) (quotation 467 F.3d taxes, ring converting eliminated tax omitted). A challenging marks defendant liability altogether ag- based on an —was give request a district court’s refusal to a gressive, although necessarily not unlaw- jury instruction “heavy ed carries the bur See, ful, interpretation of the tax code. showing] den .... that proposed his [of e.g., (testimony A II: of Belle 364/2149 charge accurately represented the law in Six) (“We did look at elimination strate- every respect, that charge actually gies Group]. The consen- [the VIPER whole, given, prejudiced viewed as a him.” them, sus was not that we wouldn’t sell Feliciano, United States v. 223 F.3d very unlikely but it would be (2d Cir.2000) (internal quotation marks Young Ernst & would ever reach a level omitted). them.”). authority to sell The Govern- ment’s comments about in rebut- COBRA Theory A. Instructions on the Defense summation, arguably imprecise, tal “while First, argue defendants light were no means unreasonable in jury instructions on Count One presented of the evidence at trial and theory omitted their of defense and unfair charged nature of ... scheme.” ly emphasized theory the Government’s Cohen, v. 427 F.3d United States guilt. Although a defendant is “entitled to (2d Cir.2005). reason, For that we find any charge jury have the court on prosecutorial the defendants’ assertions of theory defense for which a foundation ex misconduct to be without merit. record, necessarily in the he isted [is] Jury VIII. Instructions entitled to have that instruction communi jury in the language cated to his Coplan, Shapiro, argue and Nissenbaum Brand, (quota choice.” 467 F.3d at 205 jury the District Court’s instructions (alteration omitted) original). tion marks (1) respects: were flawed in three will vacate a on account of “We conviction One, the conspiracy instructions Count (1) if missing requested instruction charge, unfairly emphasized to defraud correct; legally requested instruction was theory Government’s of the case and omit- represents theory it of defense with defense; theory ted their there was in the record that would lead to basis no factual for the avoid- basis conscious *39 acquittal; theory and is not effec ance in instruction connection with Counts in Three, tively presented charge.” elsewhere Two charges; the tax evasion Prawl, v. F.3d United States the instructions on Counts Two and (2d Cir.1999) (internal improper quotation Three contained an definition of marks omitted). “economic substance.” required them case, public accountants proposed a certified

In this the defendants clients the interests of their represent to empha- One that jury instruction on Count with adversar- dealings in their vigorously acts that the distinction between sized IRS.”). ies, The District Court such as the difficult and acts job made the IRS’s more proposed of the adopted substance deceitfully dishonestly. or that were done to include the defen- charge, but declined instruction included a requested Their jury examples or to inform dants’ that, in the defen- examples of number obligations profes- of tax special about view, conspir- could not constitute a dants’ clients in an adver- represent sionals who defraud, acy in order to advance the to setting.38 sarial le- theory that their conduct was defense advocacy on behalf of their gitimate ruling We affirm the District Court’s See, (proposed A e.g., clients. VI: pro- primarily because the defendants’ instruction) (“It illegal simply is not jury “accurately repre- posed charge did not harder. is job every respect.” to make the IRS’s This Felici- the law ] sente defendants, ano, marks (quotation true for the whose 223 F.3d at 116 particularly omitted). purportedly The of attorneys examples as or professional obligations men, suggest conspiracy I to that these respect defraud do not mean 38. With to to only impede the charge, jury are the actions that could the District Court instructed the means, by nor IRS fraudulent or dishonest as follows: expressing any I view as to whether am conspiracy the United States A to defraud actually examples conduct similar to these necessarily cheating involve does not you place That’s for to decide. took here. government money property. out of or impedes the lawful Not all conduct conspiracies also includes to inter- statute agency illegal. government is functions of a government any fere with or obstruct lawful unlawful, To be that conduct has to entail fraud, deceit, any by function or dishonest fraud, deceit, means. It or other dishonest you I that the IRS is an means. instruct job illegal simply make the IRS's is not to agency government. of the United States Only agreement engage harder. an to "conspiracy The term to defraud the United IRS, impede conduct that tends to means that the defendants States" therefore fraudulent, also involves or dishon- deceitful alleged co-conspirators are ac- and their means, illegal agreement constitutes an est impair, conspiring impede, to ob- cused the United States. defeat, by fraudulent or dishonest defraud struct or means, necessary government It is not that the or the lawful functions of IRS to actually a financial loss from IRS suffer lawfully taxes and to collect due ascertain conspiracy a scheme. A to defraud exists owing tax revenue. agreement impede, when there im- is Only is intended to conduct both defeat, obstruct, any pair, fraudulent or govern- impede the of a lawful functions manner, or dishonest the lawful functions agency or ment and is fraudulent dishonest deception of the IRS. One cannot use or support charge conspiracy will a to de- defeat, impede, impair, dishonest means to government agency. conspiracy A fraud a IRS, protect legiti- even to or obstruct government impede of a the functions position. mate agency by fraudulent or dishonest means Where, however, agreement there is an altering may things include such docu- obstruct, impede, impair, or defeat the law- they ments after have been demanded fraudulent, de- government creating ful functions of the IRS agency, false docu- ments, records, means, destroying making ceptive, or the first ele- false dishonest statements, regardless of whether the attempting to induce others to ment is satisfied statements, doing particular in- engaging any means of so in that make false in and deceptive conduct that stance are or are not unlawful other fraudulent or impairing the abili- themselves. would have the effect of here, object alleged ty government agency the first that's to determine That’s By giv- defrauding aspects the IRS and the United States. material transaction. added). gentle- (emphasis ing you examples, AVI: these ladies and 419/6157-59

89 fraud, deceit, means.”). proffered by lawful conduct the defendants or other dishonest following: agreement included the “an be- whole,” “[Vliewing charge as a we find tween witnesses not to tell the government Ainar-Marshall, no prejudicial error. 336 something specifically unless asked about F.3d at 170.

it; attorney advice from an ato client to right

assert his constitutional not to speak B. Conscious Avoidance Instruction government investigators; an agree- The argue defendants further ment not to a create document that indi- there was no factual basis for the obligation viduals had no to create.” A VI: conscious avoidance instruction in connec Although these acts are not neces- Three, tion with Counts Two and the tax deceitful, sarily bright no line rule ex- “ charges. evasion ‘A conscious avoidance supporting cludes such acts from a con- permits jury instruction a to find that a spiracy to defraud. See v. Cont’l Ore Co. defendant had culpable knowledge of a fact & Corp., Union Carbide Carbon 370 U.S. when the evidence shows that the defen 690, 707, 1404, 82 S.Ct. 8 L.Ed.2d 777 dant intentionally confirming avoided (1962) (“[I]t is well settled that acts which ” Quinones, fact.’ United States v. 635 legal are in themselves lose that character (2d 590, Cir.2011) F.3d (quoting Unit they when become constituent elements of Ferrarini, 145, ed States v. 219 F.3d scheme.”). an unlawful are not un- We (2d Cir.2000)).39 A conscious avoidance in sympathetic to the view that a defendants’ struction is appropriate only when “a lay jury may struggle fully apprehend defendant asserts lack of some specific obligations professionals of tax zeal- aspect of knowledge required for convic (and ously lawfully) representing clients tion,” and “the appropriate factual Nevertheless, before the IRS. because predicate exists, i.e., charge for the the current understanding of the Klein evidence is juror may such a rational doctrine categorically does not exclude the reach the beyond conclusion a reasonable acts, foregoing properly District Court doubt that the defendant was aware of a the proposed examples omitted from the high probability of dispute the fact in jury instructions. consciously confirming avoided that fact.” event, any the Court’s actual instruc- 260, v. Ferguson, United States 676 F.3d tions on repeatedly emphasized Count One (2d Cir.2011) (quotation marks omit jury the need for the find ted). The Government need not choose defendants acted in a deceitful or dishon- between an knowledge” “actual and a “con est manner in order to convict. A VI: theory. scious avoidance” United States v. (“Only conduct that in- both is 419/6158 (2d Kaplan, 490 F.3d n.7 Cir. impede tended to the lawful functions of 2007). government agency and is fraudulent or case, In this the Government support charge requested dishonest will conspir- acy government to defraud a a conscious avoidance agency.... instruction con- Not all conduct impedes the lawful nection with the scienter element of government Three, functions of a agency illegal. is Counts Two and the tax evasion unlawful, To be that conduct has to entail charges. objected defense that there S.A., - U.S. -, recently 39. We have noted that Su "[t]he SEB 131 S.Ct. (2011)). preme appears prefer appel Court to now & n. 179 L.Ed.2d 1167 Because ” parties lation ‘willful blindness.’ v. United States used the term "conscious avoid (2d below, Ferguson, 676 F.3d 278 n. 16 Cir. ance” we continue to use that term for 2011) (quoting Appliances, purposes Global-Tech Inc. v. case. this *41 of SISG and his role as the head plan’s the conscious predicate for was no factual fees, instruction; setting the Add-On involvement the District Court avoidance evidence to allow there was sufficient objection, finding unspecified overruled the that, not Coplan if did charge. jury to conclude support to “adequate evidence” knowledge that the fees ex- have actual that the knowl- jury instructed The was 1.0%, he “decided not to learn if a defen- ceeded would be satisfied edge element fact,” v. Rodri- key States high probability that th[at] “was of a dant aware (2d Cir.1993). 455, 458 For guez, lacked a 983 F.2d transaction a CDS add-on shelter reason, conscious we conclude that the profit” and “act- that possibility of reasonable with appropriate instruction was purpose to avoid learn- avoidance ed a conscious respect Coplan. whether or not the ing the truth about of a possibility a reasonable shelter had factual basis for the conscious profit.” Shapiro instruction as to avoidance presents ques- a much closer Nissenbaum conclude respect Coplan, we With reversing are tion. Because we Counts the conscious avoidance instruction that respect Three with Two and February In clearly justified. was insufficiency on the and Nissenbaum based commented on a reviewed and Coplan ante, evidence, II.B, Part we see from Belle Six he received spreadsheet not, not, reach their chal- need and do provid- clients and that listed Add-On avoidance instruc- lenges to the conscious client. information about each ed basic tion. reflected the cost of the spreadsheet That po- maximum investment and the client’s Economic Substance Instruction C. the investment— payout

tential ratio for argue also Finally, to eval- the defendants points necessary three data two of Two and Three the instructions Counts profit potential. Specifically, uate of “eco- improper contained an definition the investment spreadsheet showed in- The District Court 0.5% nomic substance.” taxpayer approximately for each cost loss, that the Add-On transac- jury the maxi- structed the and that desired “economic substance” if taxpayer each was tion lacked payout mum ratio for possibil- offered “no reasonable (profit premium). transaction approximately 2:1 in a that the transaction would result (describing payoff ity the 2:1 See note ante ratio). variables, taxpayer it the relevant had profit,” From these two in the purpose” engaging “no business profit poten- Add-On lacked apparent that challenge The defendants transaction.40 tial if the fees exceeded 1.0%. Given Co- Now, say your me a few words about respect let 40. With to the economic substance test, there jury as to whether or not Court instructed determination District possibility was a reasonable shelter follows: profit. in a This element re- would result In to establish that a transaction order you objective judgment substance, quires to reach an government lacks economic government proved about whether the has beyond prove two elements a reason- must possibility was no reasonable that there The first element is that there able doubt: profit. in a the shelter would result possibility that the trans- was no reasonable words, upon depend other this does profit. The action would result in a second taxpayer profit what the believed about the taxpayer that the relevant had no element is requires you all of engaging potential. It to consider purpose for in the trans- business and reach a conclusion about question apart from the creation the evidence action in government proved beyond has whether of the tax deduction. that there was no rea- a reasonable doubt *42 inconsistently that within possibility the “no reasonable circuits.” Modern Controversies, profit” Practicing would result in a lan- Tax 957 Law transaction Inst, (summarizing “disjunc in the first element of the instruc- at 478-35 guage tive, tion, conjunctive, instead a transaction lacks arguing unitary formulations” doctrine).41 only economic substance where there is the economic substance “no market risk.” exception. Our is In Circuit no United Atkins, approved States v. we an instruc- matter, general

As a a transaction tion that a transaction lacks economic sub- will not pro that lacks economic substance subject stance if it was to “no market Fergu vide the basis for a tax deduction. (2d Cir.1989) 135, risk.” 869 F.2d 140 Comm’r, (2d 98, v. 29 F.3d 101 son Cir. a (upholding charge that the transaction at 1994). A transaction lacks economic sub issue lacked economic substance if it if it “can with stance not reason be [sic] was “not intended either to make or pre- substance, purpose, utility said to have or any profit any serve or to limit a loss from apart anticipated tax conse [its] way,” subject it was to no market Comm’r, 584, quences.” Lee v. 155 F.3d “changes prices risk in market (2d Cir.1998) (quotation 586 mark omit any cannot have (quotation effect” marks Comm’r, ted); see v. 915 also Jacobson omitted)). In (2d Cir.1990) (“A Regan, United States v. 937 832, F.2d 837 sham (2d 823, Cir.1991), F.2d 827 we suggested, analysis requires transaction a determina expressly ruling, without “no mar- a any tion prac whether transaction has ket risk” instruction was erroneous on the ticable economic effects other than the (internal particular facts of that case. Most recent- creation of income tax losses.” omitted)). ly, nonprecedential disposition, ap- in a we quotation marks proved instruction that a transaction substance, The law of economic it must lacks economic substance when there is said, clarity. be is not a model of possibility “no reasonable that the transac- was, economic “if substance doctrine not profit.” tion would result in a formulated, popularized” by then at least (2d Pfaff, Fed.Appx. States v. Judge Learned opinion Hand’s Helver Cir.2010) omitted). (quotation marks In (2d Cir.1934), ing Gregory, v. 69 F.2d 809 holding, so we noted that the “narrower aff'd, Gregory Helvering, v. 293 U.S. previously we approved definition” did (1935). 55 S.Ct. 79 L.Ed. 596 David “state the outer limits of the economic Hariton, Sorting P. Tangle Out the Eco substance doctrine.” Id. Substance, nomic 52 Tax Law. (1999). inconsistencies, Gregory, Despite Since the economic sub these we return applied premise stance doctrine “has been differ transaction lacks ently from circuit to circuit and sometimes economic substance if it “can not [sic] possibility profit government’s theory sonable on the tax and find defen- guilty. shelter after the were fees other costs dants not

paid. you government (paragraph If find that the has A VI: breaks omit- 424/6176-77 ted). proved beyond a reasonable doubt possibility there was no reasonable of a 2010, Congress finally codified the eco- profit, you then move on to the second element, nomic substance doctrine at 26 U.S.C. taxpayer whether the relevant had 7701(o). applies pro- § The codified version purpose engaging no for in the tax business you spectively to transactions entered into after government shelter. If find that the 30, 2010, proved inapplicable therefore has not the lack of a reasonable March is possibility profit, you reject of a then must to this case. (2d substance, Pfaff, v. 619 F.3d United States purpose, to have reason be said Cir.2010). anticipated utility apart [its] from (em- Lee, 155 F.3d at 586 consequences.” a criminal sentence We review added). presence phasis Given “reasonableness,” which “amounts early in our for- reasonableness standard for abuse of discretion.” United review substance doc- mulations of the economic *43 (2d Cavera, 180, 187 v. 550 F.3d States trine, that the District Court’s we now hold banc). Cir.2008) (en re “Reasonableness that the transac- possibility “no reasonable the length an examination of requires view instruction, profit” in a tion would result (substantive reasonable the sentence of 40, ante, accurately the note stated see ness) employed in procedure well as the as law. rea (procedural at the arriving sentence sonableness).” Johnson, v. States United Prejudice “Spillover” IX. Cir.2009). (2d 40, A district 567 F.3d 51 that, argues should his conviction Coplan error where it procedural court commits One, Two, Three, or Seven be on Counts calculates) (or improperly to calculate fails overturned, obligated would be this Court treats the Guidelines range, the Guidelines (obstruction Five of the to vacate Count to consider mandatory, as fails IRS), Be- “spillover prejudice.” based on 3553(a) factors, § selects a sentence based in affirm conviction its Coplaris cause we facts, ade clearly erroneous or fails to on Vaughn entirety, reject argument. we this sentence. quately explain chosen Gall improp- argues allegedly likewise that the States, 38, 51, 128 v. United 552 U.S. S.Ct. er venue on Six and admission Count (2007). We have 169 L.Ed.2d coconspirator statements caused of review for substan previously likened our spillover. reject argu- We this prejudicial tive unreasonableness “to the consider ment, rejected predicates. we its jury criminal ation of a motion for a new trial, only when granted which should be X. Procedural and Substantive ‘manifestly unjust,’ jury’s verdict was Reasonableness of Bolton’s and to the determination of intentional Sentence actors, which be torts state should if the tort ‘shocks the only alleged found Finally, challenges procedur- Bolton Dorvee, conscience.’” States v. al reasonableness of his and substantive Cir.2010) (2d (quoting 616 F.3d noted, previously 15-month sentence. As 583 F.3d 122- Rigas, United States v. guilty Superseding to a pleaded Bolton (2d Cir.2009)). charging Information him one count of § conspiracy, in violation 18of U.S.C. Proceedings Sentencing A. (1) conspira- objectives: with three Klein (2) Government and Bol- cy; making parties false statements to the —the (3) ton, IRS; stipulated plea of the IRS. On in this obstruction context— (1) special that “under the facts of appeal, agreement Bolton contends that the Dis- defendant, there concluding applicable that his this case trict Court erred (c) §in 2T1.1 of § 371 resulted in a “tax is no ‘tax loss’ as defined conviction under Guidelines; Bolton A 36. meaning Sentencing Guidelines.” loss” within that Bolton’s ad- imprison- stipulated sentence of 15 months of It was further his unreasonable; substantively visory range ment Guidelines would be to 6 ap- of if the imposed by imprisonment million fine the months Court $3 2T1.9, § or 10 to 16 months light plied be vacated in U.S.S.G. District Court should imprisonment applied if the Court loss excess of million. He then $400 § 2J1.2. The Pre-Sentence Re- U.S.S.G. imposed a sentence of impris- 15 months of port of the Office calculated U.S. Probation onment, noting that my finding “if on loss advisory range Guidelines of 0 to 6 incorrect, is the sentence would still be the imprisonment § under months of 2T1.9 substantial, same because this is a massive recommended a sentence 6 months departure.” Bolton A117. imprisonment. sentencing In its sub- mission, the Government agreed B. Procedural Unreasonableness applicable Probation Office that the Guide- months, range lines was 0 to 6 but urged argues Bolton on appeal that the Dis- impose Court sentence above that trict Court procedural committed error range based the factors set forth in 18 *44 2Tl.l(a) § applying though even he was 8553(a). § U.S.C. essence, convicted of tax evasion. Bolton contends that a “tax loss” within 29, 2010, By January Judge order dated the meaning of the only Guidelines exists appear Stein ordered counsel to at a hear- where a defendant willfully evaded taxes ing order to discuss “several issues” or committed certain “specific other in- related Bolton’s Guidelines calculation. tent” crimes. At hearing, Judge explained Stein “huge problem” that he had a with the applicable § Guideline 371 con- parties’ stipulation that no tax loss was 2T1.9,42 § spiracy convictions is which attributable to Bolton under the Guide- states that a defendant’s base offense level Specifically, lines. Judge Stein stated that shall greater be the of 10 or the offense “intellectually he could not be honest” and 2T1.4, § § level determined from 2T1.1 or adopt position that there was no tax appropriate. as Section 2T1.1 is entitled loss, light attributable to Bolton in of his Evasion; “Tax Willful Failure to File Re- Stein’s) (Judge conclusion that the tax loss turn, Information, Supply Pay Tax; or attributable to the trial defendants exceed- Returns, Statements, Fraudulent or False ed million. April At the $400 or Other Documents.”43 Section 2T1.4 is sentencing hearing, Judge Stein applied 2Tl.l(a) entitled “Aiding, Assisting, Procuring, § advisory and calculated an Counseling, or range Advising Guidelines of 210 to Tax Fraud.”44 262 months of imprisonment based on an estimated tax provision, Under either the base offense (2) provides, 42. part: Section 2T1.9 in relevant if there is no tax loss. Obstruct, Conspiracy Impede, Impair, 2Tl.l(a). § or U.S.S.G. Tax Defeat (a) (Apply greater): Base Level Offense provides, part: 44.Section 2T1.4 in relevant (1) Offense level determined from Aiding, Assisting, Procuring, Counseling, or 2T1.4, § § appropriate; 2T1.1 or or Advising Tax Fraud (2) 10. (a) 2T1.9(a). § Base U.S.S.G. Offense Level: (1) (Tax Table) § Level from 2T4.1 corre- provides, part: Section 2T1.1 in relevant loss; sponding to the tax or Evasion; Return, Tax Failure to File Willful if there is no tax loss. Tax; Supply Information, Pay or Fraudulent purposes guideline, For of this the "tax loss” Returns, Statements, or False or Other Docu- loss, 2T1.1, resulting § is the tax as defined in ments aid, assistance, procu- from the defendant’s (a) Base Offense Level: (Tax Table) rance or advice. § Level from 2T4.1 corre- loss; 2T1.4(a). sponding § to the tax or U.S.S.G. But sentencing.” Mr. Bolton’s “tax the close of by calculating the is determined level below was sentencing about the nothing loss” for the offense. the Court deter- “cursory.” Although 2Tl.l(c)(l), a “tax loss” is §to Pursuant range Guidelines applicable mined that the as follows: defined it imprisonment, 262 months of was 210 to tax evasion or a involved If the offense of 15 ultimately imposed a sentence return, false statement fraudulent or the low 93% reduction from months —a document, the tax loss is the total other range. Inasmuch as Bolton’s end of that object of loss that was amount clearly was not driven sentence {i.e., have the loss that would offense calculation, the Court’s initial Guidelines the offense been successful- resulted had impose that it would same statement ly completed). in the absence of a loss sentence even 2Tl.l(c)(l). § The definition U.S.S.G. For supported by the record. amply is to “the tax loss reference measures reason, “confidently we can conclude” in the nothing the offense.” But object of error here was harm- any arguable of a “tax limits the existence definition Id. less. acted to instances where defendant loss” Unreasonableness C. Substantive intended to cause willfully or otherwise *45 argues that his 15- Bolton also Thus, the title although IRS. loss to the substantively unrea month sentence § clear that 2T1.1 provision makes “unrea the District Court sonable because willful on tax evasion and other is focused sonably weighted the seriousness of [his] laws, nothing in the violations of the tax evidence, particularly offense based on § 2T1.1 application limits the language in to the E & Y defendants.”46 comparison Assuming arguendo that to such crimes.45 fact that given Br. 28. But Bolton applying err the District did Court necessary played significant Bolton 2T1.1, § that error would be harmless be conspiracy (by coming up role explicitly cause the District Court stated story signing cover IRS the Add-On the same sentence impose it would documents, example), as well as his See regardless of the loss amount. United gain implementing financial (2d significant Jass, 47, v. 569 F.3d 68 Cir. States transactions, it cannot be said that his 2009) (“Where er identify procedural we un “manifestly sentence was 15-month sentence, the record indicates ror in a but F.3d at 122. just.” Rigas, See 583 would have clearly that the district court event, in any sentence imposed the same Imposed D. Fine on Bolton harmless, avoid may the error be deemed Finally, argues Bolton the Govern vacate the sentence and to ing the need to —and (internal fine im the million sentencing.” agrees ment $3 remand the case for —that omitted)). be va posed by the District Court should marks Bolton at quotation Pfaff, v. light cated in of United States significance to minimize the tempts (2d Cir.2010), which was decided by characteriz F.3d 172 District statements Court’s sentencing. after Bolton’s “cursory” observations “near four months ing them as note, however, trial defendants were skepti- 46. The sentences of the our considerable 45. We (36 months), applying Coplan the wisdom of an intend- Mar- cism about Robert as follows: where, (30 months), measure ed rather than actual loss Shapiro Richard tin Nissenbaum here, has not been convicted of (20 months). the defendant months), (28 Vaughn Brian specific requiring him to have the a crime loss. intent to cause a tax that, jury ing we held in the absence of a Pfajf, conspiracy violation of 18 371, § finding, may impose a district court U.S.C. are REVERSED due greater statutory evidence; fine than the default to insufficient provided máximums U.S.C. b. The convictions of 3571(d). (“[I]t § is the clear Id. at Nissenbaum on Counts Two and implication Apprendi Blakely Three, charging tax evasion in viola- jury pecuniary when a does not make a § tion of 26 U.S.C. are RE- § gain finding, or loss 3571’s default statu insufficient VERSED due to evi- tory cap máximums the amount a district dence; defendant.”). Further, may court fine the c. Nissenbaum’s conviction on Count in the time period sentencing between Four, charging him with obstruction hearing filing in this case and the of this of the IRS in violation of 26 U.S.C. opinion, Supreme decided Court § is REVERSED due to in- States, Southern v. Union Co. evidence; sufficient squarely holding that “the rule of Appren proper Venue was with respect applies imposition di of criminal Six, Count which charged Vaughn - -, fines.” U.S. S.Ct. with false statements to the IRS in (Sotomayor, 183 L.Ed.2d 318 1001; § violation of 18 U.S.C. J.). (4) The District err by Court did not indisputable It is that the District Court admitting testimony of Graham impose could not a fine in excess of the Taylor; $250,000. statutory maximum of See 18 (5) The District Court did not err 3571(b)(3). § Accordingly, U.S.C. we va- admitting the out-of-court statements portion cate the of Bolton’s sentence that *46 alleged of the coconspirators; fine, imposed the and remand the cause to (6) The District Court did not err the District for the sole of purpose Court excluding portions Coplan’s of and reducing statutory the fine to the maxi- Vaughn’s deposition transcripts; $250,000. mum of (7) prosecutorial There was no miscon- CONCLUSION duct the Government’s rebuttal summation; presided The District Court over this (8) by: The District Court did not err complex and difficult case with admirable care and understanding declining give “theory of its intricacies. a. to instruction; defense” summarize,

To we hold that: including b. a conscious avoidance (1) challenge The to the defendants’ so- instruction; or conspiracy theory called Klein of instructing jury c. that “econom- liability criminal under 18 U.S.C. only if there ic substance” existed § 371 fails the law of the under Cir- possibility” was a “reasonable of cuit, good which remains law absent profit; review or modification the Su- Court; preme (9) Spillover prejudice did not infect the convictions; (2) remaining and respect sufficiency With chal- lenges: portion of Bolton’s sentence Shapiro imposing a.The convictions of and a fine is VACATED and One, charg- Nissenbaum on cause is REMANDED for the sole Count On”); Personal Investment Cor- fine to the and reducing of purpose (“PICO”) $250,000. poration shelters. statutory maximum of at 54. “The IRS Majority Opinion ante holdings, judg- light of these resulting from a can deductions disallow Vaughn of Coplan ments of conviction with reason that ‘can not [sic] transaction AFFIRMED, of con- judgments are substance, or purpose, to have be said are Shapiro viction of and Nissenbaum tax con- utility apart anticipated from [its] REVERSED, of the District portion are said to sequences. Such transactions sentencing principal- Bolton Court’s order ’ ” Majority lack “economic substance.” is AF- ly imprisonment to 15 months of with (quoting, ante at 58 n. 15 Opinion FIRMED, of Bolton’s portion and the Commissioner, alterations, Lee v. 155 F.3d a million fine is VA- imposing sentence $3 Cir.1998)). (2d 584, 586 is REMANDED CATED and cause reducing the fine purpose for the sole superseding One of the indict- Count $250,000. statutory maximum of four alleged that each of the above ment respect to defendants Sha- Judgment other, shelters, along with one tax enter on all piro Nissenbaum, and Nissenbaum shall fraudulent, Shapiro, and that which we have reversed the counts as to Coplan Robert and defendant —each District judgment Court. Master’s De- lawyer whom was a with a experience gree in tax law and decades of KEARSE, dissenting in Judge, Circuit persons other known practice tax —and part: unknown, agreed to de- conspired I from so much of respectfully States, dissent to violate the fraud the United Majority Opinion as finds the evidence laws, and to make false federal income (1) the convictions support insufficient to Majority statements to the IRS. As the Martin of defendants Richard Opinion acknowledges, the evidence as conspiracy, in violation of Nissenbaum conspiracy’s objectives is not deficient (a) § defraud the United 18 U.S.C. if there is sufficient evidence of least by impairing the lawful functions of States objectives. Majori- alleged one of the See govern- States agency of the United ty Opinion ante at 62-63. Govern- “[T]he ment, wit, the Internal Revenue Service sought ment to demonstrate the de- *47 (b) (“IRS”), evasion, see 26 commit tax from the IRS fendants hid the truth (c) 7201, § make false state- U.S.C. and withholding making information and affir- IRS, § to the 1001 ments see U.S.C. mative misstatements” about these shel- (2) (Count One); those two defen- 58, and ters, Majority Opinion ante at IRS attempted convictions of tax evasion dants’ with a audit interviews and in connection (Counts § in violation of 26 U.S.C. amnesty program 2000 IRS that would Three). Two and in tax person allow a who had invested shelters, legit- if them not the IRS deemed out, Majority Opinion As the sets this transactions, penal- paying imate to avoid prosecution principally focused ties on those transactions. audit design, implementation, Majority suggest does not developed of four tax shelters The defense (“E Y”) jury there insufficient evidence for the Young & LLP & [Ernst ] (1) with conspiracy that there existed a Contingent to find Group/SISG: VIPER (“CDS”); Currency objectives alleged Swap one or more of Deferred it, given Nor could that Co- Reward Alternatives Count One. Options Bring (“Add- (“COBRA”); Vaughn, Brian a certi- plan and defendant CDS Add-On accountant and certified finan- duce public Extraordinary fled Results —and whose Y, E planner employed by cial & were name changed was later to Strategic Indi- (see participating alleged (“SISG”) convicted of in the vidual Solutions Group Gov- (“GX”) conspiracy 73), and that we affirm con- ernment those Exhibit which mar- Rather, (see Majority victions. finds that keted tax shelters Trial Transcript 1069). (“Tr.”), 4619, the evidence was insufficient Coplan to show that was the lead- Shapiro and Nissenbaum knew of the con- er “high of this net worth market group” (Tr. spiracy 4619-20); in it. participated Majori- See and Nissenbaum ty (see, Opinion ante 62-63. were core e.g., members id. at 2135- 2236). Majority Opinion out the sets well trial, government At introduced nu- legal principles established “[i]n merous e-mails between or among Shapiro, conviction, context of a conspiracy ‘defer (and Nissenbaum, others) and Coplan dis- jury’s ence to the findings especially is alia, cussing, inter the need to prevent important ... a conspiracy by because its materials, certain which E mentioned & Y very nature is a operation, secretive and it clients’ interest in minimizing or eliminat- aspects is a rare case where all of a con taxes, ” ing falling from into the hands of court,’ spiracy can be Majori laid bare the IRS. These included: ty Opinion (quoting ante at 62 — (Coplan GX 795 e-mail dated No- (2d Rojas, States v. 617 F.3d “ 27, 2000, vember copies to Shapiro, Cir.2010)); government ‘the is enti others, among stating, “we refrain from prove solely through tled to its case cir ” sending leaving out—or with a client— evidence,’ Majority Opinion cumstantial promotional materials that go through ante at 69 (quoting United States v. Rodri steps of a strategy, highlight or even (2d Cir.2004)); guez, 392 F.3d the tax benefits of a strategy. Business evaluating sufficiency chal “[i]n purpose is a critical element to prove for lenge, we ‘must view the evidence in the solutions, these and the less evidence light government, most favorable to the there is that the client responded to a crediting every inference that could have tax-saving promotion, the better his favor, government’s been drawn in the argument that there were non-tax moti- deferring jury’s assessment of wit guiding vations his actions.” (emphasis credibility ness and its assessment of the ” added)); weight of the Majority Opin evidence.’ — (Shapiro GX 860 e-mail May ion dated (quoting ante at 62 v. United States 22, 2001, Merk, Chavez, (2d to Melinda a member of 549 F.3d 124-25 Cir. 2008)). group who PFC worked with SISG But in finding the evidence insuffi (see 1281), Tr. stating general that “as a cient to permit jury to infer that Sha *48 rule, presentation materials piro and SHOULD conspir Nissenbaum knew of the NOT be left with the acy it, client. Clients participated and in the Majority notes, etc., may take but apply does not materials principles. these should be handed back at the end of the meeting. In an meeting audit i [sic] A. Conspiracy Count Minneapolis had in on a COBRA trans- Y, firm, action, E & an accounting had a Per- one of requested the items of the (“PFC”) sonal Financial Counseling group taxpayer any promotional materials that included a group, initially they called VI- had.” in (capitalization origi- nal)); acronym PER —an for Value Ideas Pro-

— (Merk be out the window.” from would dated No- COBRA e-mail GX 795 added)). an E & Y tax (emphases to vember “I am stating employee department subparts 1-4 and below in As discussed any provide and prepare to hesitant below, pre- government also Part B delivery potential summary for to witnesses, in- testimony many from sented client, my recent conversa- based on cluding Bob Shapiro and tions with Richard — Thomas partner E & Y tax former very careful about that we be Coplan that, in the A. who testified Dougherty, writing in such information providing others, he lied Shapiro and presence into the dissemination potential in connection with the CO- to the IRS receipt n by me- marketplace and/or ” shelter, “plau- false making but BRA added)); dia, Treasury.... (emphases he dis- had representations sible” — July e-mail dated (Coplan GX 555 Shapiro; with cussed 17, 2001, employees, 60 E & Y to some — Nissenbaum, Kathryn E & Y client Mun- “in- former including Shapiro and ro, immediately delete to statements made— struct[ing to who testified them] in any and all materials her E dispose not made—to statements computers drawers and with investments [their] [their] & Y connection other shelters, transaction related to COBRA and with re- and Add-On CDS re- letters and documents opinion than” amnesty misleading false and spect to currency to the client’s trades lated by E & Y for submis- prepared letters supporting the economic “documents IRS; sion to the and bona nature purpose fide — manager E & Y Jason former (emphas- in the transaction” investment Munro Bryant Rydberg, who dealt with added)); es to, alia, prepara- inter and testified — July e-mail dated (Coplan GX 602 misleading opinion let- tion of false and 23, 2001, Y employees, to some 60 E & following and letters to the IRS its ters Nissenbaum, re including Shapiro and amnesty regard to CDS offer of Leak,” stating that a Materials “PICO shelters, Add-On tax and testified of E & Y’s potential client had sent set requirement presenta- E & Y competitor, to an E & Y PICO materials regard tions with to those shelters be sug- was “not although Coplan and that to Shapiro; shown in advance necessarily is a calami- gesting that this — manager E & Y Belle Six— former event[, negative re- potential tous t]he a total of some million who earned $22 obvious, are and a percussions fax of selling both from CDS commissions [including] people materials to certain with, Y working while at E & shelters have calami- government WOULD ” others, and Nis- Shapiro, Coplan, among origi- (capitalization tous results senbaum, selling E & Y Add- and from nal)(other added)); and emphasis plead- thereafter —who had On shelters — e-mail dated June (Coplan GX 639 conspiring to defraud guilty ed 14, 2000, regional an E & Y senior required and had been government re “Fi- manager, copy with a govern- that total to the pay or forfeit Slides,” stating, Add-On nal Set CDS *49 (see 2106-10); ment Tr. and alia, ever inter these slides “[i]f — practicing lawyer Peter Cin- ... former IRS way made their to the to, pleaded guilty who had argument quegrani, purpose entire business alia, give with others to conspiring inter ability distinguish this gives us false false statements and documents mid-March Sullivan received with the the IRS connection PICO notice from the IRS that the WRB Lake shelter, having Shapi- collaborated with partnership being was audited. He in- so fashioning opinion ro in letters PICO Dougherty, formed who in turn informed Cinquegrani testified he knew con- fax, Coplan by e-mail and Coplan which misleading tained false and statements to, others, among forwarded Shapiro, Nis- (Tr. 4015). story” a constituting “cover (see senbaum, and Denis Conlon Tr. 1171- 75), a member of E & Y’s national tax 1. Shapiro and COBRA practice specialty whose responding Shapiro was the E & Y leader on the (see 540; contacts from the IRS GX Tr. presentation national roll-out of the CO- 1175-76). In a early conference call in 4588.) BRA tax shelter Tr. {See April, Dougherty discussed with Coplan Dougherty about the principally testified and Conlon the “facts that could hurt the professed purported of (Tr. 1186). —and —interests client’s case” Dougherty, [sic ] partnership three members of a called Coplan, and Conlon ... come “tr[ied] WRB Lake who invested in a COBRA tax up may with some ideas that presented he Dougherty shelter. been had instructed agent why for [IRS] WRB the[]” by E & Y’s tax division director to ask two partners Lake entered the COBRA trans- of those & Y clients Bill partners Wan- —E (id. added)), action at 1182 (emphases even Sullivan, ner and Brian whose business though Dougherty, Coplan, and Conlon purification was water and desalinization transaction, “knew that this was a COBRA were a a selling company profit who at one all three principals had entered into of more than million each—whether $20 (id. 1181). ... savings” to realize the tax at they were in E & interested Y’s CDS Dougherty testified: (see 1081-86) strategy id. at to convert discussion, At point this we’re income, ordinary their have which would looking taxpay- at other reasons that the rate, been taxable at about a 40% into together purposes ers came for the long-term which capital gains, would be why they purchase foreign digital did (see 2149). taxable at generally 20% id. at contracts, why they together did do this However, Sullivan, along Wanner and partnership, why they in a did de- another Lake partner, WRB informed partnership cide to terminate that Dougherty they were interested in- any foreign currency not do more invest- stead in a strategy whereby taxes on their ing. just transaction would be not minimized (Id.) Dougherty possible advanced various (Id. 1087.) but at After E “eliminate[d].” explanations, including that Wanner had COBRA, & Y decided to market its tax business, prior experience, some (see had his 1088-89), strategy elimination at id. doing foreign currency trading, some partners sought WRB Lake “to enter “maybe something that was we could into COBRA transaction ... for the being throw out as supporting purpose eliminating tax on the transac- fact ” entering reason into this transaction they going through”; tion were the clients (id. added)), (emphasis although at 1182 they pursuing said interested in “w[ere] (id. Dougherty 1183), Wanner had indicated to for that at purpose” [COBRA] (see 1181-83). outset, any such motivation id. at they and in 1999 From the did so. Dougherty Wanner had “also talked about the fact that stated his “desire to enter partners] happened into the transaction for the three Lake purposes [WRB COBRA (Id. 1141.) creating joint newly a tax loss.” to be investors in formed [a] *50 reason” that was the “same why “they purpose” explain which could company,” dis- and Conlon had Dougherty, Coplan, willing partnership to form a would be in their purposes business partnership possible cussed carry and on some together they “to talk about would earlier call: needed Maybe activities. that investment reasons, reasons, plausible at 1182 other something {Id. be we could use” added).) ... it become al- could be discussed should Dougherty had (emphasis meeting at the important to discuss that “the real ready Coplan told and Conlon added).) clients; is, (emphases agent.” how with the history {Id. these behind and the they Young to Ernst & came ensuing that in the Dougherty testified 1736.) at transaction.” {Id. COBRA interview, IRS attended May the three “They knew those facts about Conlon, Dougher- Dougherty, Shapiro, and 1738.) talking at “We were clients.” {Id. agent why “about ty “lied” to the IRS pre- that could be plausible about reasons partners] got three Lake into [WRB sented”; with some up “we needed to come 1743.) (Tr. COBRA transactions.” took why reasons the transaction business plausible “the Dougherty gave agent place.” form it took at place {Id. in the during reasons that we had talked about added).) (emphases discussions, misleading were which at among Dough- agent pwpose.” {Id. After that conference call as to the real added).) Conlon, Dougherty erty, (emphases sent 1743-44 Coplan, and Conlon made an e-mail dated testified that the Dougherty Coplan “[statements [he] and 19, 2001, why the clients had stating they agent needed about April this, gone ... had Shapiro join thinking things [he] have GX 542 done were {see (“I Mr. during Coplan, think Richard.... I want to over the calls with Mr. we need Conlon, clearly correctly Shapiro.” from and Mr. at 1743 {Id. state our case and added).) (emphasis IRS would like to catch beginning.... hurt get cold and admissions that will us alone, events From this series of need to make sure that does our case. We that, with re- jury permissibly could find happen.”)). Accordingly, April COBRA, Shapiro knowingly spect Conlon, 2001, Coplan Dougherty, e-mailed conspiracy in the joined participated and “call Shapiro to schedule a conference impair the law- Coplan and others to go ... the facts of with all us over make ful functions of the IRS and to false approach will plan this case and how we the IRS. statements to (Tr. 1188.) agents on this matter.” Shapiro and CDS Add-On CDS call April, In late a conference was held Conlon, addition, was E & Y’s “sub- among Dougherty, Coplan, Shapiro call, “SME”—on its Shapiro ject expert” raised matter Shapiro. During —or (Tr. 4555), which would con- strategy Tr. CDS question purpose of business {see 1741-42), ordinary long-term income into saying high need to discuss vert “[w]e (taxable gains at about half the rate purpose capital business on this transaction” {id. 1191). income), however, ordinary and on the Add- Dougherty, al- of such “[h]ad” which, 636), when ready point strategy at that the On GX Shapiro {see “told Mr. transac- year had used in the second of a CDS real about how these clients facts tion, liqui- would involve the creation and Young come Ernst & the COBRA even the (emphasis at 1741 add- dation of an LLC and eliminate transaction.” {Id. ed).) The SME had the “techni- Coplan, capital gains. Con- Dougherty, reason (Tr. i.e., 4876), lon, he “was the “discussing expertise” were business cal

101 (GX added).) that knew the transaction the best out.” person (emphases 66 Shapiro went to you ques- and that’s who for added that fact that “[t]he no materials are (id. 4555) (id). approval” at and “for tions” to left be behind at a call sales is not example, regional For a senior manager enough. my opinion, before anything is Shapiro forwarding sent an e-mail to a here, in ‘stone’ we should consider what presentation Power Point to “for are record [sic] look like.” will/should (GX 30, approval as the CDS SME.” dated (Id. added).) (emphasis And in an e-mail 1999.) 22, in October And to a response Vaughn models,” to about “cds copies presentation proposed by Power Point Nissenbaum, others, Coplan, to Shapi- and Add-On, Vaughn for Coplan stated that ro instructed that certain “deletions” from “the Add-On will all of strategy lose its “essential,” model documents were if it purpose’ steps ‘business is reduced to “ that the statements that ‘Calculations as- objective in a PowerPoint The slide. sume Early utilization of the Termination (GX will appear driving to be the force” ’ (GX ... Provision should be deleted.” 14, 2000, (Coplan 636 e-mail dated June to 2000.) dated April Vaughn, with copy Shapiro)); Coplan to using recommended not slides and recom- (“Bolton” Bolton Capital Planning or mended that all “materials like this” “BCP”) general partner was the in some should be reviewed in by Shapiro, advance (See, LLPs created for CDS shelters. e.g., (id.). as the Add-On “SME” 1231.) 2215-16, 2477; Tr. GX After Bol- Success of the involving CDS shelter — ton an inquiry received from the IRS with partnership that in engage swap was shelter, regard to a Coplan CDS revised purportedly having transactions a term of language the initial draft of the BCP 18 depended swap’s on the termi- months — response to the inquiry IRS to state that nation year after one but short of the 18- general partner, “[i]f based on market month stated termination year date. One fluctuations, swap terminates con- dividing was the line between short-term early, capital gain tracts would arise capital gains long-term capital gains; (GX (Coplan such termination” e-mail prior termination to the end of the stated added))). January (emphasis dated 18-month term required gains was for (Tr. 2321) Six testified that this “does not” be capital gains treated as rather than “accurately describe what ... clients” 2198-99.) (See, ordinary income. e.g., Tr. early were “told ... about termination and Shapiro repeatedly urged that the fact that how the decision early was made to termi- early pre-planned termination was not be (id. 2320). swaps nate” the CDS at 8, 2000, On February disclosed. he sent decision was not to be made based on Merk, an e-mail to with copies to Nissenb- ” fluctuations; “understanding market aum, Coplan, Vaughn, on “the [CDS] we assumed we would “[t]hat termi- plan”; action suggesting addition to nate, early terminate ... if the counter- he, Shapiro, along with Coplan Vaughn, (Id. party did not.” (emphases should be involved in any CDS sales con- added).) The revised language GX tact, Shapiro noted “the swap our fact day had been introduced the previous will be early terminated ”—and noted that Coplan Shapiro, e-mail from Nissenb- “[cjlearly this was ... necessary aum, others, with the statement “ques- transaction” —and he flow of acceptable “This one should be more ... seriously” whether there tioned] (GX 932, January “should ... be a Richard.” dated document existence 2318-22.) 2001; ... chapters has all and verses laid Tr. see *52 (See id. at those misstatements. repeated observation Shapiro’s with Consistent 3524-41.) necessary for “early” termination was strategy but should not of the CDS success that, E contrary to the Munro testified described, E & Y client Mun- former be so letters, representation “[w]e Y drafted & her that when she and husband ro testified as a partnership] not invest in [the did shelter, they were had invested a CDS invested financial investment. We sound 18 swap had a duration of not told that That pay less in taxes. in it so we could simply told it would They months. were the transaction.” purpose the basic (See 3548; at Tr. see also id. year. a last 3525.) (Tr. Contrary representation to the maturi- testifying that “the (Rydberg letters, coherent busi- wasn’t sound “[i]t in the used ty swap that[ was] date of the specific It was a transac- strategy. ness months; was 18 “[w]e transaction” CDS taxes”; nobody help our tion to us reduce it would last 12 months and told [clients] Young to talk[ed] [Munro] “from Ernst & date”); at early termination id. day to the philosophy a coherent business about (“all transactions ha[d] CDS transaction.” with the CDS connection “12 early ... termination date” of same (Id.) Contrary opinion to the letters— day”).) one months and representation on the which were based “purpose testified that the Munro also predeter- in fact “had a letters —the CDS was to de- Munros’ transaction CDS] [the ... the outcome was mined outcome liability [they] until sold” fer [their] income to ordinary capi- the conversion of had received from shares that her husband what tal income. And that’s gains options of stock “and could the exercise of the transaction was about.” purpose (Tr. 3539; see pay capital gains tax.” 3530-31.) (Id. Contrary opinion at to the 3530-32.) id. at In 1999 also letters, partnership formed Munro respect in 2001 with to respect to CDS and for the had no and her husband CDS Add-On, “repre- the Munros Rydberg sent plan of the plan”; “overall business “[t]he sign and return in sentation letter[s]” ordinary in- partnership was to convert from a law firm opinions order to receive by exercising your op- you come that had legitimacy of their investments capital gain. it So tions and convert (Id. 3519-24, at 4637- CDS and Add-On. primary purpose pay less taxes was 38.) Munro testified that these were let- (Id. 3531-32.) at partnership.” really” read before ters that she did “[n]ot informed Munro of the Rydberg (id. 3524), having “paid at a lot of signing amnesty and E & Y draft- program, IRS’s for tax money Young to Ernst & advice” and her amnesty letters for Munro ed (id. 3526; see, (Rydberg at e.g., at id. Add-On, respect husband with to CDS and testifying that he told clients “the fee[ ] signed by the Munros and which were percent ... was 4 transaction th[e CDS] (See the IRS. Tr. were submitted to being generated”); the loss that was id. 3550.) 3545-46, Munro testified that those (the Munros, for their CDS transac- on the amnesty letters —which were based tion, $400,000)). E Y Munro testi- paid & (a) business opinion letters and described letters were representation fied that (b) have, that the Munros did not purposes they in that misstated misleading false and purpose not mention the Munros’ did her for which she and hus- purpose (c) taxes, stated Add-On; reducing had invested in CDS and band (see facts any letters did not omit material letters received opinion and the pertain- GX 1231 as (describing id. at 3546 opin- with the Munros—who did not deal ing pertaining E and GX 1232 as through firm & Y— CDS ing except law Add-On)) (see situations,” misleading gain false and stated that “the 1999 —were 3544-50). Tr. and 2000 clients that have completed a transaction” shortly CDS would be “no- IRS, amnesty The Munros’ letters to the ... of opportunity tified] to partici- in March had been drafted submitted (GX pate in the trading program.” new by Rydberg. Rydberg testified that his 633.) Shapiro responded: “i remain [sic] for Add-On followed a re- template draft concerned of the formal pre-wired tie-in to *53 (See, Coplan. e.g., ceived from Tr. 4657- cobra, i think adversely impacts [sic] it 491.) 58; template GX Drafts of that had story that we regarding can tell to, others, by Coplan among been e-mailed (Id. purpose of the transaction.” (empha- 27, Shapiro February and Nissenbaum on added).) sis Coplan then edited the letter (see 490), 5, GX and on March to be sent to announcing clients Add-On (see 491). e-mail, Coplan GX In the latter and, 1, 2000, July an e-mail dated to stated “Please look this over to see if there Six, Merk, Shapiro, Vaughn, and Nissenb- any changes you are would make either to aum, stated, “I softened the last reference unnecessary avoid facts or to make it easi- liquidation to the of the interest accurately. er to I want complete post to LLC so it an sounds less like event that I morning. this and distribute this will be we know happen will in the near future.” sending along template CDS later this (GX added).) However, (emphases (Id.) morning....” re- Nissenbaum liquidation part was eighth LLC of the sponded Coplan, copy Shapiro, to with a to specified that were steps necessary for that, believing other than to details as the success of an Add-On transaction. specific option unnecessary, trades to be (See 18, (Vaughn May GX 115 e-mail dated (id.; disclosure fine me” “[t]he looks to see Coplan Shapiro).) to and As Six 4663); Shapiro provided Tr. and some non- testified, “liquidation of the in the interest adopted substantive comments that were in fact “was one steps LLC” of the (see 4663-65; Tr. compare GX 491 with required was to obtain the tax benefits.” 492). “[tjhroughout GX But these various (Tr. 2410.) generic amnesty drafts of the add-on template, ... description basic of the Shapiro and PICO (id. transaction the same” remain[ed] at (or 4665); Personal Investment and those drafts omitted mention of PICO Cor- poration) tax-minimization or tax shelter was a tax deferral pur- tax-elimination (see 491). poses strategy GX and conversion that involved in- vestments in an S corporation, called Although the Add-On strategy CDS PICO, by taxpayer and another share- (see Vaughn was the brainchild of Tr. engage holder. The would in strad- PICO 2378-79), reality Add-On was in a combi- generated offsetting dle transactions that (see nation of and id. at CDS COBRA losses, gains only and with allo- losses 1378-81). Both of the latter were shelters taxpayer. capital cated to the These loss- (see E Y promoted by Shapiro to & id. at taxpayer es could be used to offset (CDS); (COBRA)), 2144-46 id. at 4588 gains his from sources. capital unrelated (see Shapiro was the SME for Add-On GX (See 3736.) Tr. 636). in a June Vaughn, 2000 e-mail to early numerous E & Y tax department employ- Cinquegrani, attor- ees, copies Shapiro, Coplan, with ney approached, opinion who was for an Nissenbaum, letter, by person noted the add-on who had conceived “[w]ith feature, applied capital Cinquegrani can now be and who instructed CDS PICO description”; in such lead not been set forth Shapiro, E & Y’s Richard

contact 3739^42.) about (See samples nothing said Shapiro’s but Tr. contact for PICO. (Id.) tax ramifications. the transaction’s initial conversation Cinquegrani’s he some testified that added any Cinquegrani there was no discussion Shapiro, Shapiro’s sample representations non-tax reason for purpose or business (see 3743-44.) (See opinion ensuing version of PICO id. PICO. 3777); the substance of two Tr. legal to have is- Cinquegrani proceeded pur- non-tax business samples asserting researched, in- kept Shapiro he sues appeared representations as client poses (See, Tr. 3748- e.g., of the results. formed (see, e.g., letter GX Cinquegrani’s opinion 49.) with Sha- many He had conversations 663). “discussing] provisions various piro, knew he testified that he may apply Cinquegrani Internal Revenue Code that transaction, that was mislead- drafting asked about was document [Shapiro] *54 of the ing purpose as to the true PICO being were or were not includ- what issues (id. 3773); in engaged that he was in the at and Cin- transaction and opinion” ed (See 3761.) exam- Tr. For wrongdoing. memoranda and drafts to quegrani sent by stating ple, description began the fact Shapiro, Coplan who forwarded them to (see 3751-54, qualified inves- offering 3769- that the “is and Nissenbaum id. at LLC investors’) (‘the 70). opportunity summaries of the tors Cinquegrani sent man- special purpose in create a investment requested to be included conclusions letter, on proposed agement company capitalize fact opinion [the and drafts facts, foreign exchange in the expertise as LLC’s] sections—based on “assumed” (id. general manage- investment were no clients at the time markets and there PICO 3752-53) services”; that already- Cinquegrani ment testified support at —to (see that not an accurate statement be- legal reached conclusions id. at 3750- 54; offering this (“by [Cinquegrani] cause “the real reason for id. at 3761 the time section,” vehicle, PICO, provide is to drafted facts the PICO which is the [this] (Id. 3754-56.) at largely in its final tax losses for investors.” opinion letter “was form”).) description contained other false or (see id. at misleading statements as well receiving Cinquegrani’s After draft of 3756-61), de- although because PICO was section, Shapiro Cinquegrani the fact sent to the investor signed make available “[t]o repre- listing an e-mail economic-substance (id. 3758), Cinquegra- at significant losses” that been made in connec- sentations had the transac- ni’s “intention was describe transaction, stating tion with different ordinary possible tion as much as sending that he was them for discussion all the tax downplay business deal and to tone, etc., purposes specifically “as to (id. 3756), “deemphasizing at aspects” (GX e-mail dat- (Shapiro for content.” (id. tax benefits” at possible wherever (bold 7, original)).) August ed 3760). any E expressed No one at & Y Shapiro’s sample representations first four the letter. language concerns about the referred to “substantial non-tax” business (See 3761.) id. at transaction; the last purposes for the sum, testified that there Cinquegrani reviewed the stated has “[i]nvestor story begin- element contained in was a “cover description of transactions about description ning opinion the Letter and is accurate misleads such (Tr. what the transaction is all about” complete, pertinent and there are no 4015) opinion and that the letter contained relating facts to the Transactions that have — 8, false misleading Shapiro’s statements were February 2000 e-mail (see 3754-81), indeed, “wildly CDS, id. at mis- GX “seriously” “ques- (id. 3779). at leading” Cinquegrani was tionfing]” whether the ... “[c]learly nec- why asked he not tell “Shapiro” did essary” “fact that swap our will be ter- opinion others that the letter contained a minated early” should be included “a (Id. 4021.) story. false cover Cinqueg- document”; rani that he testified “didn’t feel a need to — Shapiro’s April 2000 e-mail on oh, say, way, the stuff we are CDS, GX terming it “essential” that “ writing really really doesn’t reflect what’s the statements that ‘Calculations as- on,” going key players, because “the sume Early utilization of the Termi- ” mentioned, you others], Mr. [and nation Provision’ “be deleted” from the they all participated creating story.” documents; model (Tr. 4021-22.) — e-mail, Coplan’s July GX 144, stating despite the fact that liqui- — 4. Nissenbaum dation of the interest in the LLC was Nissenbaum too awas core member of fact a step required that was in order to (See the SISG headed Group Coplan. planned achieve the tax benefits —that 2236.) 2135-37, Tr. I disagree with the Coplan had “softened the” Add-On an- Majority’s view that the evidence was in- nouncement letters’ “reference to the *55 sufficient a permit to reasonable inference liquidation of the in interest the LLC so that Nissenbaum knew of participated it sounds less like an event that we know in the conspiracy impede to the IRS in the happen will in the near future.” performance of its lawful functions. I nothing see that required jury to As the Shapiro above discussion of re- regard Nissenbaum as a disinterested re- veals, Nissenbaum too received numerous cipient of random e-mails. These were e-mails from Coplan, as well as several communications sent to him as a core from Shapiro, urging concealment of facts member of the SISG group, pre- which that were material to the tax-minimization pared presentations, prepared templates COBRA, goals tax-elimination of the clients, for prepared letters to and for CDS, Add-On, and PICO shelters. templates responses to IRS inquiries. These included: Plainly Nissenbaum did review e-mails — 17, e-mail, Coplan’s July 2001 GX regard sent to him with to letters to be 555, ordering retention of documents seeking amnesty. sent to the IRS in With “supporting the economic purpose and PICO, regard Dougherty testified that bona fide nature of the investment in the prepared he a disclosure using letter (emphasis transaction” add- [COBRA] “amnesty ... template coming from Mr. ed), along legal opinions and docu- (Tr. 1761; Nissenbaum” see id. at 1317- trades, ments relating currency 18); and that template did not “disclos[e] but ordering the immediate deletion and [taxpayer’s] all the entering motives” for disposition any of other relat- materials (id. 1762) into the transaction at and did COBRA; ed to primary not “mention the motivation of — 23, (id. 1761). e-mail, Coplan’s July 2001 GX deferring reducing taxes” at 602, Leak,” about a “PICO Materials Nissenbaum approved (prepared the letter stressing that leaking “of the materials from his template) without substantive (GX (Nissenb- ... government change go” WOULD have as “Good to results”; 18, 2002); calamitous aum April e-mail dated see also 499, States, 492, 63 S.Ct. 1641). Add-On, 317 U.S. Co- United regard to Tr. With (1943). The jury L.Ed. 418 solicited—and received—comments plan instructed, alia, find that it inter could amnes- proposed on the Nissenbaum from of these of- guilty substantive defendants (which adopted misstatements ty template principle estab- fenses on the basis by E & Y letters opinion in the received States, 328 in v. United lished Pinkerton letters, turn, having clients, opinion in 90 L.Ed. 66 S.Ct. U.S. representa- from the form prepared been (1946), when the evidence establishes (see, GX 786 e.g., the clients tion letters for existed, member of the conspiracy (e-mail 30, 2001, from Brent March dated held liable for all of conspiracy may be acts Clifton, opin- attorney who wrote Add-On coconspir- performed by other wrongdoing letters, and Nis- Shapiro, Coplan, ion during the course of and further- ators 2486-88)). senbaum); amnesty Tr. 646-47, conspiracy, of see id. ance tax- not disclose the templates did letter 66 S.Ct. 1180. ie., motive, actual tax-elimination. payer’s only suggestion was to elim- Nissenbaum’s Vaughn were Coplan and convicted otherwise, details; some investment inate One and of conspiracy alleged Count said, fine to me” he disclosure looks “[t]he offenses al- tax evasion substantive (GX (Nissenbaum March e-mail dated Two and Three. Given leged Counts 5, 2002, see Tr. Coplan and Shapiro); supports convictions evidence 4663). Shapiro and Nissenbaum of Count above, in Part A conspiracy, One discussed reasonably argued can it be Nor easily find that jury could import of did not realize the Nissenbaum Vaughn by Coplan evasions were In March any these nondisclosures. and were conspiracy furtherance a region- when he became aware that I foreseeable to and Nissenbaum. department employee Y tax had al E & *56 against the verdicts uphold would thus department em- to some 18 other sent Two Nissenbaum on Shapiro and Counts de- ployees presentation a Power Point theory. and Three on the Pinkerton shelter, scribing an SISG tax Nissenbaum region rejects applicability to of the director that The Majority instructed “nothing substantially from SISG theory it clear” that “[f]or “make the Pinkerton (GX widely” Majority this that” the re- is to be circulated the reasons would (Nissenbaum Nis- Shapiro e-mail dated March the convictions of verse (bold stated, conspiracy, Majority original))). Opinion in Nissenbaum senbaum for is, Majority than this sooner ante at That views “This could shut down (Id.) IRS!” to the infer- sending permit the PowerPoint to the evidence insufficient as knew Shapiro

ence that and Nissenbaum and Nis- Shapiro B. The Convictions in con- the Count One participated of and Three senbaum Counts Two ie., they in fact mem- that were spiracy, conspiracy. bers of the supersed- Two and Three of the Counts view, in In the evidence my and Nis- discussed charged Shapiro indictment ing offenses, wit, ample jury permit Part A was to with substantive to above senbaum Shapiro and Nissenbaum in of 26 to infer tax evasion violation attempted in the participated proven §-7201 in the Add- knew of and connection with U.S.C. Each was a core member prohibits conspiracy. tax shelter. Section 7201 On SISG, E tax-shelter-marketing arm of conduct, of which “any likely effect e-mails, conceal,” Y; they received numerous Spies v. & be to mislead or would Coplan, cautioning against proffer could to the IRS in connection with principally from marketing E & Y materials those allowing the audit of the Lake partners WRB but to fall into the hands of “the IRS.” shelters also attended the IRS interview at which warnings explicitly similar were is- And Dougherty told such And both “lie[s].” them- by Shapiro and Nissenbaum sued Shapiro ap- and Nissenbaum reviewed and warnings and selves. The numerous stat- proved form letters to be submitted E maintain files need not goal ed sanitized IRS, Y in support & clients to the themselves have been unlawful order amnesty, proffered business purposes, show, did, they Shapiro as and Nis- not did disclose tax-reduction tax- fully were aware of the efforts to senbaum motivation, elimination and stated that no purposes conceal the tax of these shelters sum, pertinent facts were undisclosed. from the IRS. And the evidence was suffi- I conclude that the evidence was sufficient permit jury cient to to infer that Sha- support the convictions of piro engaged and Nissenbaum mislead- Nissenbaum of conspiracy charged plainly conduct unlawful. ing Count One and of the substantive offenses Shapiro, example, only discussed Dougherty they charged false statements that Two Three. Counts APPENDIX A *57 B

APPENDIX by or force or threats of way corruptly RELEVANT STATUTORY any threatening letter or (including force PROVISIONS communication) impedes, or or obstructs impede, or the due endeavors to obstruct Conspiracy § to Commit 18 U.S.C. 371— shall, title, upon con- administration of this Offense or to Defraud United States thereof, be fined not more than viction persons conspire either If two or more $5,000, not more than 3 imprisoned or any against commit offense United both, if the offense is years, except or States, States, or or to defraud United force, only threats of committed any thereof in manner or for any agency fined not convicted thereof shall be person of any and one or more such purpose, $3,000, not more imprisoned more than or object of persons any do act to effect The term “threats of year, than 1 or both. conspiracy, each shall be fined under subsection, force”, as in this means used more than five imprisoned this title or not bodily of harm to the officer or threats years, or both. or to a employee of the States United family. member of his If, however, offense, the commission object conspiracy, of which is the is (b) property Forcible rescue seized only, punishment

a misdemeanor for of the maxi- conspiracy such shall not exceed forcibly Any person who rescues or punishment provided mum for such misde- any property to be after it causes rescued meanor. title, or shall have been seized under this do, shall, attempt shall or endeavor so to Attempt § to Evade or U.S.C. 7201— for, provided excepting cases otherwise Defeat Tax offense, every such be fined not more Any person willfully attempts in who $500, than double the than or not more any any manner to evade or defeat rescued, property value of the so whichev- there- imposed by payment this title or the greater, imprisoned er or be not is shall, penalties pro- of in addition to other 2 years. more than law, and, felony guilty vided be thereof, shall be upon conviction fined § or Entries 18 U.S.C. 1001—Statements $100,000($500,000in the more than case Generally not more corporation), imprisoned or (a) Except provided as otherwise this both, years, together than 5 or with the section, whoever, any matter within the prosecution. costs executive, legislative, jurisdiction of the Attempts § to Interfere U.S.C. 7212— judicial branch of the Government of the with Administration Internal Reve- States, willfully— knowingly and *58 nue Laws (1) falsifies, conceals, up by or covers (a) Corrupt trick, scheme, or a material any or device forcible interference fact; or force or corruptly Whoever (2) fictitious, false, any materially makes (including any threatening threats of force representa- fraudulent statement or or communication) letter or endeavors to in- tion; or any employee timidate or officer or impede or acting any writing in an official makes or uses false of the United States title, any knowing the same to contain capacity under this or other document false, fictitious, any materially matters, or fraudu- administrative including a entry; lent statement or claim payment, for a matter related procurement of property or title, imprisoned shall be fined under this services, personnel employment or or, years not more than 5 if the offense services, practices, support or or a international involves or domestic terror- law, rule, document required by or (as 2331), impris- ism defined in section regulation to be submitted to the years, oned not more than 8 or If both. Congress or any office or officer the matter relates to an offense under branch; within legislative or 109A, 109B, 110, chapter or or section (2) any review, investigation or conduct- 1591, then the term im- imprisonment pursuant ed authority any posed under this shall be not more section committee, subcommittee, commis- years. than 8 sion or Congress, office of the con- (b) (a) apply par- Subsection does not to a sistent with applicable rules of the ty a judicial proceeding, party’s or that House or Senate. counsel, statements, representations, writings or documents submitted such

party or to a judge magistrate counsel

in that proceeding.

(c) respect any With matter within the branch,

jurisdiction of the legislative sub- (a)

section shall apply only to—

Case Details

Case Name: United States v. Coplan
Court Name: Court of Appeals for the Second Circuit
Date Published: Nov 29, 2012
Citation: 703 F.3d 46
Docket Number: 10-583-cr(L)
Court Abbreviation: 2d Cir.
Read the detailed case summary
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