Defendant-Appellant Morris Zukerman appeals from a judgment of conviction entered on March 21, 2017, in the United *426States District Court for the Southern District of New York (Torres, J. ). After pleading guilty to tax evasion and to corruptly endeavoring to obstruct and impede the due administration of the internal revenue laws, Zukerman was sentenced to pay restitution of $37 million, serve a 70-month term of imprisonment, and pay a $10 million fine. On appeal, this case calls on us to determine whether the fine imposed was procedurally and substantively unreasonable. It was not. In particular, the district court did not err in calculating the fine range recommended by the Sentencing Guidelines; Zukerman was given adequate opportunity to inform the district court of his financial condition and ability to pay a fine; and the imposition of a $10 million fine was within the district court's discretion. Accordingly, the judgment of the district court is AFFIRMED.
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Morris Zukerman is the founder of M.E. Zukerman & Co., an investment management firm also known as "MEZCO." In 2007, a MEZCO subsidiary sold certain assets for $110 million, at which time Zukerman enacted a scheme to avoid paying taxes on the proceeds of that sale, as well as on approximately $12 million of operating income MEZCO received as a result of its earlier ownership of those assets. Zukerman falsified several documents in order to effectuate this scheme, which allowed MEZCO to evade over $30 million in taxes. When aspects of these transactions were audited by the Internal Revenue Service in 2008, Zukerman lied to the tax professionals working for him and fabricated documents relating to the transactions, causing several false statements to be made to the IRS. See In re Grand Jury Subpoena Dated March 2, 2015 ,
Separate and apart from those activities, Zukerman engaged in several other schemes to avoid paying taxes and to throw the IRS off of his trail. He avoided paying over $4.5 million in state taxes related to paintings used to decorate his and his families' living quarters, which were purchased, in part, with his ill-gotten gains from the MEZCO tax evasion. In addition, he provided false information in connection with his personal tax returns, as well as those of his family members and his household employees, causing each of them to file false tax returns over the course of several years. When the personal taxes of both Zukerman and his daughter were audited, Zukerman once again provided false documentation and representations to the IRS. Finally, Zukerman also failed to file several years' worth of tax returns for the Zukerman Family Trust despite the trust's receipt of significant taxable income.
On June 27, 2016, Zukerman pleaded guilty to tax evasion, in violation of
Following oral argument, we subsequently entered a summary order pursuant to United States v. Jacobson ,
On appeal, Zukerman contends that the fine component of his sentence was procedurally and substantively unreasonable. Because Zukerman did not raise any procedural objections below, his procedural arguments are "deemed forfeited on appeal unless they meet our standard for plain error." United Statesv. Villafuerte ,
Zukerman's first procedural argument is that the district court overlooked U.S.S.G. § 5E1.2(h) in calculating the Guidelines' recommended sentencing range, which had the effect of doubling the recommended fine. That provision states that an earlier version of the Guidelines should be applied "[f]or offenses committed prior to November 1, 2015." Count One of Zukerman's indictment alleges that his corrupt endeavors to obstruct and impede the due administration of the internal revenue laws occurred "[f]rom in or about 2007 through in or about 2015," however, and Zukerman averred during his plea allocution that the conduct underlying Count One took place "from 2007 through 2015." Jt. App. 60, 99. One cannot reasonably interpret "through 2015" to mean only prior to November 1, 2015. Moreover, Zukerman's plea agreement expressly recognized the applicability of the Guidelines range of which he now complains. That the district court did not apply the pre-November 1, 2015 Guidelines to Zukerman was not an error, much less a plain error.
Nor is there any merit to Zukerman's contention that inadequate consideration was given to his ability to pay a $10 million fine. As soon as the district court set a date for sentencing, it foreshadowed that a major fine was possible, requesting information concerning "how fines have been calculated" in "cases where you have this degree of violation of law." Jt. App. 107. Zukerman subsequently submitted an affidavit regarding his financial condition as of August 2, 2016, at which time his net-worth was in the eight-figure range. Zukerman now contends that the affidavit was outdated by time he was sentenced in March 2017, but he declined to provide updated information in any of several submissions he made to the district court after receiving a revised Pre-Sentence Report on November 9, 2016, which incorporated information regarding his financial condition from his August 2016 affidavit. His failure to do so continued even after the government expressly asserted that he could "pay a substantial fine and should be ordered to do so-through a substantial variance from the $25,000 to $250,000 Guidelines range" in February 2017. Id. at 322. At his sentencing hearing, Zukerman objected neither specifically that he could not afford to pay the fine imposed, nor more broadly that his financial condition had materially changed since the submission of his affidavit. He was afforded ample opportunity to attempt to show any limitations on his ability to pay a fine, yet he failed to do so. See United States v. Elfgeeh ,
We next address the substantive reasonableness of Zukerman's fine, which we review "under a 'deferential abuse-of-discretion standard,' " United States v. Thavaraja ,
First, the district court "put significant weight on the nature and circumstances of [Zukerman's] crimes" pursuant to
Zukerman counters that these factors do not support an upward variance from the recommended fine range because they were already addressed as part of his offense level under the Sentencing Guidelines. But the district court was not bound to conclude that the offense level adequately accounted for the complexity and scope of Zukerman's actions. To the contrary, "the historic role of sentencing judges," which "continue[s] to be exercised," is to consider "the judge's own sense of what is a fair and just sentence under all the circumstances." United States v. Jones ,
Second, and again pursuant to
Third, the district court "put the most weight" on the need for deterrence, pursuant to
Zukerman also summarily argues that it is "obvious" his fine is not necessary for purposes of specific deterrence in light of his prison term and the "pain and humiliation his prosecution has caused." Def. Br. 43-44. Although there can be little doubt Zukerman has suffered, we "must give due deference to the district court's decision" that specific deterrence justified an upward variance in light of Zukerman's long-running tax evasion scheme, *430Gall , 552 U.S. at 51,
Fourth, the district court recognized that there was some risk of an unwarranted sentencing disparity, but it "assigned less weight than it might typically have" to this factor because it found "few, if any, defendants" who were similarly situated. Id. at 12. Although Zukerman's fine is certainly an outlier as compared to the fines typically imposed in tax cases, his arguments based on aggregated sentencing data and vague summaries of other cases are unconvincing. The relevant question is not simply whether there are disparities, but whether there are "unwarranted sentence disparities" as between Zukerman and others "with similar records who have been found guilty of similar conduct,"
*431Fifth, the district court "looked to
Although Zukerman now asserts that the district court erred in considering the gap between his restitution and the estimated tax loss, as well as the absence of interest in calculating the tax loss, he cites no authority for the proposition that the district court could not take these factors into account. Indeed, these seem pertinent considerations in ensuring that Zukerman would not ultimately profit from his tax evasion. See
Sixth, the district court "accorded significant weight to [Zukerman's] income and financial resources, as well as the limited burden of a $10 million fine." Supp. Mem. at 15. Zukerman contends that he is being unfairly punished because of his wealth, but
It stands to reason that a defendant's wealth is relevant in determining whether a particular fine will deter illegal conduct. Zukerman implies that sentencing judges should consider only whether a defendant is unable to pay a given fine, but nothing in the text or history of the Guidelines, let alone common sense, suggests that this is meant to be a one-way ratchet. A fine can only be an effective deterrent if it is painful to pay, and whether a given dollar amount hurts to cough up depends upon the wealth of the person paying it. Indeed, as noted above, a previous "$233,000 slap-on-the-wrist" did not deter Zukerman, with his extraordinary resources, from subsequently evading his taxes once again. Supp. Mem. at 11. We therefore join our sister Circuits in holding that a defendant's wealth and earning capacity are *432pertinent considerations in assessing an appropriate fine. See United States v. Teel ,
Lastly, the district court "put substantial weight" on the payment of restitution by "corporate entities," as a result of which "only the fine would be paid from [Zukerman's] own pocket." Supp. Mem. at 15. Zukerman responds that restitution was properly paid by MEZCO because it was MEZCO's tax evasion that caused most of the tax losses at issue and, in any event, payments made by MEZCO are tantamount to payments made by him. The latter point appears to be somewhat disingenuous, as elsewhere Zukerman takes the position that he no longer has any interest in MEZCO for purposes of asserting that the district court overestimated his net worth. Zukerman cannot have it both ways: if he no longer owns MEZCO and believes that its value is not attributable to him, it follows that he should not be credited with MEZCO's restitution payments.
Regardless of MEZCO's current ownership, however, a more fundamental principle remains: "Restitution is an effective rehabilitative penalty because it forces the defendant to confront, in concrete terms, the harm his actions have caused." Kelly v. Robinson ,
Focusing on each facet of the district court's reasoning individually, rather than their totality, is to miss the forest for the trees. The district court concluded that Zukerman, a very wealthy man who has repeatedly and brazenly committed sophisticated tax fraud-a rarely caught and more rarely punished offense that undercuts the functioning of state and federal governments-ought to pay a fine hefty enough to take any financial benefit out of his crimes and to give pause to others who might be tempted to commit similar crimes. The district court further concluded that the Guidelines range did not encompass a fine necessary to accomplish those ends. Instead, the district court calculated the size of the fine based, in part, on an estimate of the tax loss Zukerman caused less the amount of restitution he had agreed to pay. Zukerman's fine thus "resulted from the reasoned exercise of discretion." Cavera ,
For the foregoing reasons, we AFFIRM the judgment of the district court and DENY Zukerman's motion to stay his sentence pending this appeal as moot. We have considered all of the defendant's arguments and find in them no basis for vacatur.
Zukerman's third procedural argument-that the district court's explanation of his sentence was inadequate-is moot in light of our Jacobson remand.
The district court noted that a longer incarceral term was not necessary in order to specifically deter Zukerman at his sentencing hearing, but it referenced the totality of his experience with the criminal justice system-including the fine imposed upon him-as necessary to achieving that end. See Special App. 38 ("I do not think that there is a need for a term of imprisonment at the higher end of the guidelines range in order to achieve the goal of specific deterrence. I have confidence that this experience throughout this case has gotten that message across loud and clear.").
The only tax offender Zukerman discusses with specificity is Robert Pfaff, who was sentenced to 97 months' imprisonment and fined $3 million. As explained by the district court, however, there are myriad distinctions between Zukerman and Pfaff: (1) Pfaff designed and implemented fraudulent tax shelters on behalf of others but was not a direct beneficiary of the tax loss he caused, whereas here the tax loss directly benefitted Zukerman and his family; (2) Pfaff was convicted alongside two co-defendants, whereas Zukerman was the sole director of the scheme at issue; (3) Pfaff had no history of uncharged criminal conduct, whereas Zukerman had been dodging taxes for year prior to the conduct for which he was ultimately indicted; and (4) Pfaff had lost his entire net worth by time of his sentencing, whereas Zukerman still enjoyed a $35 million net worth. But even assuming arguendo that Pfaff and Zukerman were similarly situated, the disparity in their sentences points in both directions: Pfaff's fine may have been smaller, but he was also sentenced to an additional 27 months' imprisonment as compared to Zukerman. As a result, we cannot say whose sentence was more lenient. Cf. United States v. Rinaldi ,
We see no inconsistency between our holding and United States v. Mancilla-Mendez ,
Zukerman informed the district court that he transferred his interest in MEZCO to his wife as a result of the publicity surrounding his prosecution. He subsequently argued that "Mrs. Zukerman's assets are not relevant to assessing her husband's ability to pay," Def. Br. 18-19 n.3, and that assets "belong[ing] exclusively to Zukerman's wife" could not "be fairly considered in assessing Zukerman's ability to pay," Def. Reply Br. 16.
