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Full Opinion
After trial in the District of Connecticut (Janet C. Hall, Chief Judge), a jury convicted Defendant-Appellant Jesse C. Lit-vak of various charges of securities fraud, fraud against the United States, and making false statements. On appeal, Litvak challenges these convictions on several grounds.
First, Litvak contends that, for the purposes of the fraud against the United States and making false statements counts, the evidence adduced at trial provided an insufficient basis for a rational jury to conclude that his misstatements were material to the Department of the Treasury, the pertinent government entity. We agree, and accordingly reverse the District Court’s judgment of conviction as to those charges.
Second, Litvak argues that his misstatements were, as a matter of law, immaterial to a reasonable investor, which would require reversal of the securities fraud counts as well. However, because a rational jury could conclude that Litvak’s misstatements were material, the materiality inquiry — a mixed question of fact and law- — -was properly reserved for the jury’s determination.
Third, Litvak claims that, in respect of the scienter element of the securities fraud counts, the evidence was insufficient to support the verdict and that the District Court failed adequately to instruct the jury. Because Litvak is incorrect that “contemplated harm” is a requisite component of the scienter element of securities fraud, we reject this challenge.
Fourth, Litvak asserts a number of evi-dentiary errors at trial. We agree that the exclusion of certain proffered expert testimony exceeded the District Court’s allowable discretion, and that such error was not harmless. Accordingly, we vacate
BACKGROUND
The charges in this case arise from Lit-vak’s conduct as a securities broker and trader at Jefferies & Company (“Jeffer-ies”), a global securities broker-dealer and investment banking firm.
In January 2013, the government filed an indictment charging Litvak with eleven counts of securities fraud, see 15 U.S.C. §§ 78j(b), 78ff (Counts 1-11), one count of fraud against the United States, see 18 U.S.C. § 1031 (Count 12), and four counts of making false statements, see 18 U.S.C. § 1001 (Counts 13-16). The indictment alleged that Litvak made three kinds of fraudulent misrepresentations to several of Jefferies’s counterparties, some of which were Public-Private Investment Funds (“PPIFs”),
In February and March 2014, a fourteen-day trial by jury was held on the charges described above, except for Count Seven (a securities fraud charge), which was dismissed on the government’s motion
As a bond trader at Jefferies during the relevant time period, Litvak bought and sold RMBS on Jefferies’s behalf, sometimes as a middleman (holding the RMBS only briefly when facilitating a transaction between two other parties) and sometimes holding the RMBS for a longer period of time in Jefferies’s “inventory.” Joint App’x at 376. Between 2009 and 2011, Litvak made three types of misrepresentations to representatives of the counterparties with whom he transacted on Jefferies’s behalf in order to increase Jefferies’s profit margin on the transactions in which he engaged. First, he misrepresented to purchasing counterparties Jefferies’s acquisition costs of certain RMBS. For example, in the course of the transaction at issue in Counts One, Twelve and Thirteen, Litvak falsely represented to Michael Canter, a representative of the AllianceBernstein Legacy Securities Fund (“AllianceBern-stein Fund”), a PPIF, that Jefferies had purchased certain RMBS at a price of $58.00 (based on $100.00 face value), when in fact Litvak knew that Jefferies had purchased those securities at $57.50.
Second, Litvak misrepresented to selling counterparties the price at which Jefferies had negotiated to resell certain RMBS. In the course of the transaction at issue in Count Eight, for example, Litvak falsely stated to a representative of York Capital Management (“York”), a hedge fund that owned certain RMBS, that Litvak had arranged for Jefferies to resell those securities to a third party at a price of $61.25 (based on $100.00 face value). Litvak and York’s representative, Kathleen Corso, agreed that Jefferies would purchase the securities from York at a price of $61.00, in order to allow Jefferies to reap a $0.25
Third,' Litvak misrepresented to purchasing counterparties that Jefferies was functioning as an intermediary between the purchasing counterparty and an unnamed third-party seller, where in fact Jefferies owned the RMBS and no third-party seller existed. In the course of the transaction at issue in Count Eleven, for example, Litvak falsely represented to a representative of Magnetar Capital (“Magnetar”), a hedge fund, that Litvak was actively negotiating with a seller of certain RMBS (i.e., acting as a middleman) when, in fact, Litvak knew that Jefferies held the securities in its inventory. Lit-vak’s negotiations with Vladimir Lemin, Magnetar’s representative, began with Le-min’s offer to purchase the securities at a price of $50.50. Litvak then described to Lemin a fictional back-and-forth between himself and an unnamed, non-existent third-party seller, which concluded with Litvak’s false representation to Lemin that he had contemporaneously purchased the securities on Jefferies’s behalf at a price of $53.00. Lemin then agreed for Magnetar to purchase from Jefferies the securities at a price of $53.25, in order to allow Jefferies to reap a $0.25 profit (or “commission”) when resold. Id. at 543. However, the securities purchased from Jefferies by Magnetar were actually held in Jefferies’s inventory and had been acquired by Jef-feries several days prior at a price of $51.25. Lemin testified that this distinction reflected “a very different situation” from that which he understood at the time of the transaction.
At the conclusion of the trial, the jury convicted Litvak of securities fraud (Counts 1-6, 8-11), fraud against the Unit
This timely appeal followed. A prior panel of this Court granted Litvak’s motion for release pending appeal because he “raised a substantial question of law or fact likely to result in reversal.” Order, United States v. Litvak, No. 14-2902-cr (2d Cir. Oct. 3, 2014), ECF No. 41 (alteration and internal quotation marks omitted).
DISCUSSION
Litvak challenges his convictions on several grounds, four of which we reach in this opinion. First, Litvak contends that, for purposes of the fraud against the United States and making false statements counts, the evidence adduced at trial provided an insufficient basis for a rational jury to conclude that his misstatements were material to the Department of the Treasury, the pertinent government entity. We agree, and accordingly reverse the District Court’s judgment of conviction as to those charges.
Second, Litvak urges us to hold that his misstatements were, as a matter of law, immaterial to a reasonable investor, which would require reversal of the securities fraud counts as well. However, because a rational jury could conclude that Litvak’s misstatements were material, the materiality inquiry — a mixed question of fact and law — was properly reserved for the jury’s determination.
Third, Litvak claims that, in respect of the scienter element of the securities fraud counts, the evidence was insufficient to support the verdict and the District Court failed adequately to instruct the jury. Because Litvak is incorrect that “contemplated harm” is a requisite component of the scienter element of securities fraud, we reject this challenge.
Fourth, Litvak asserts a number of evi-dentiary errors at trial. We agree that the exclusion of certain proffered expert testimony exceeded the District Court’s allowable discretion, and that such error was not harmless. Accordingly, we vacate the District Court’s judgment of conviction as to the securities fraud charges and remand for a new trial on those charges. Because the other evidentiary rulings that Litvak challenges on appeal are likely to be at issue on remand, we also address those claims and conclude that the District Court exceeded its allowable discretion in certain of those rulings as well.
I. Fraud Against the United States and Making False Statements
Litvak contends that, in respect of the fraud against the United States and making false statements counts, the evidence adduced at trial was insufficient to establish the materiality of his misstatements to the Department of the Treasury — the relevant government entity. Because we conclude that the evidence was insufficient to permit a rational jury to find that Litvak’s misstatements were material to the Treasury, we reverse his convictions on those charges (Counts 12-16).
A. Standard of Review
“As a general matter, a defendant challenging the sufficiency of the evidence bears a heavy burden, as the standard of review is exceedingly deferential.” United States v. Brock, 789 F.3d 60, 63 (2d Cir.2015) (internal quotation marks omit
B. Materiality for Purposes of 18 U.S.C. §§ 1001, 1031
Litvak was convicted under 18 U.S.C. § 1001 for making false statements (Counts 13-16) and 18 U.S.C. § '1031 for fraud against the United States (Count 12). Section 1001 proscribes one from, inter alia, “knowingly and willfully ... makfing] any materially false, fictitious, or fraudulent statement or representation” “in any matter within the jurisdiction of the executive, legislative, or judicial branch of the Government of the United States.” 18 U.S.C. § 1001(a)(2); see also United States v. Shanks, 608 F.2d 73, 75 (2d Cir.1979) (per curiam) (explaining that Section 1001 was “designed to protect the authorized functions of governmental departments and agencies from the perversion which might result from ... deceptive practices” (internal quotation marks omitted)), cert. denied, 444 U.S. 1048, 100 S.Ct. 740, 62 L.Ed.2d 736 (1980). Section 1031 prohibits one from, inter alia, “knowingly execut[ing] ... any scheme or artifice with the intent ... to obtain money or property by means of false or fraudulent pretenses, representations, or promises, ... including through the Troubled Asset Relief Program, an economic stimulus, recovery or rescue plan provided by the Government, or the Government’s purchase of any troubled asset as defined in the Emergency Economic Stabilization Act of 2008----”
“[I]n order to secure a conviction under [18 U.S.C.] § 1001(a)(2), the Government must prove that a defendant (1) knowingly and willfully, (2) made a materially false, fictitious, or fraudulent statement, (3) in relation to a matter within the jurisdiction of a department or agency of the United States, (4) with knowledge that it was false or fictitious or fraudulent.” United States v. Coplan, 703 F.3d 46, 78 (2d Cir.2012), cert. denied, — U.S. -, 134 S.Ct. 71, 187 L.Ed.2d 29 (2013). For purposes of the second element, which is at issue here, “a statement is material if it has a natural tendency to influence, or be capable of influencing, the decision of the decisionmaking body to which it was addressed. ...” Id. at 79 (emphasis added).
We have not previously addressed the contours of materiality for purposes of 18 U.S.C. § 1031. Because the parties agree that materiality is an element of Section 1031, and that such requirement is coextensive with Section 1001’s materiality element, we assume as much and therefore have no occasion to address the issue here.
C. The Government’s Evidence
The government relies primarily upon the testimony of David Miller, formerly chief investment officer for the Treasury’s Office of Financial Stability,
As relevant to this case, Miller’s role at the Treasury “was to oversee the investment program[] that [was] created as a result of the financial crisis,” Joint App’x at 309, which formed and invested in the PPIFs. PPIFs were “partnership^]” between the Treasury and private investors established to purchase “troubled assets,” including certain RMBS that had “rapidly deteriorated] in value during the financial crisis.” Id. at 310; see also supra notes 2-3, 8.
Miller explained that the Treasury was responsible for overseeing the PPIFs. The Treasury selected the PPIF asset managers and prescribed rules governing “how they would invest the capital.” Joint App’x at 312. To enable the Treasury to perform its oversight duties, the PPIFs were required to provide the Treasury “access” to detailed “trade level data” upon request. • Id. at 314. Such data might be used to explore “concerns about the internal conflicts of interest that [the Treasury] wanted to be able to check upon,” such as assuring that firms with “multiple funds that invested in these type of securities” erected “certain separations and walls.” Id. In addition, Miller testified that the Treasury received “formal monthly report[s]” of each PPIF’s “top 10 positions” and “market color,”
Miller also explained, however, that because the Treasury did not have the “expertise” to purchase and manage the assets at issue, the “investment decisions were managed by the fund managers” it had selected — “expertf ]”. asset managers that “were well established in the field.” Id. at 310, 312. The fund managers were given “complete discretion over which eligible assets to buy and sell.” Id. at 323.
The government also elicited testimony regarding Miller’s prior duty to report fraud. While employed by the Treasury, if Miller received reports of fraud from
D. The Evidence Was Insufficient To Establish Capability to Influence a Decision of the Treasury
Even viewing the evidence in the light most favorable to the government, there was insufficient evidence for a rational jury to conclude that Litvak’s misstatements were reasonably capable of influencing a decision of the Treasury. Despite adducing evidence that Litvak’s misstatements may have negatively impacted the Treasury’s investments, that this impact would have been reflected in aggregate monthly reports submitted by PPIF managers to the Treasury, and that the misstatements were the impetus for an investigation by the Treasury that eventually led to Litvak’s prosecution, the government submitted no evidence that Litvak’s misstatements were capable of influencing a decision of the Treasury. To the contrary, on cross-examination, Miller’s testimony was unequivocal that the PPIFs were deliberately structured in a manner that “[kept] the Treasury away from making buy and sell decisions.” Id. at 319. To that end, Miller explained, the Treasury cast itself as a limited partner in the PPIFs, and retained “no authority to tell the investment managers” which RMBS to purchase or at what price to transact.
In defending Litvak’s convictions for' fraud against the United States and making false statements, the government advances three grounds for affirmance, each of which we find unpersuasive. First, the government suggests that a jury could reasonably conclude that Litvak’s misstatements stymied certain PPIFs from transacting RMBS “at the best possible prices,” thereby impeding the Treasury’s ability to reap optimal returns on their investments in those funds. Gov’t Br. at 43 (quoting Joint App’x at 316). Nevertheless, even if a rational jury could accept the underlying assertion — that Litvak’s misstatements ultimately, though indirectly, frustrated the Treasury’s achievement of its investment goals — it may not then infer solely therefrom that those misstatements were capable of influencing a decision of the Treasury. Such speculation is not permitted; rather, for a jury to so conclude, the government must have adduced evidence of an actual decision of the Treasury that was reasonably capable of being influenced by 'Litvak’s misstatements. See United States v. Gaudin, 515 U.S. 506, 512, 115 S.Ct. 2310, 132 L.Ed.2d 444 (1995) (“Deciding whether a statement is material requires the determination of ... [the] question[ ] ... what decision was the agency trying to make?” (internal quotation marks omitted)). To form the basis of a jury’s conclusion, evidence of such a decision cannot be purely theoretical and evidence of
Second, the government suggests that we may affirm because “the information the PPIFs reported to [the] Treasury was affected by Litvak’s conduct.” Gov’t Br. at 45-46. Viewing the evidence in the light most favorable to the government, we accept that Litvak’s misstatements resulted in the PPIFs with which he transacted buying or selling RMBS at slightly lower or higher prices than they would have absent the misstatements. It may follow that the government’s underlying contention — that information reported to the Treasury was “affected” by' Litvak’s misstatements — is accurate insofar as the monthly reports submitted by the PPIFs to the Treasury reflected marginally higher or lower aggregate balances in light of the prices at which RMBS were bought or sold in the transactions at issue. See id. at 46. However, even if the PPIFs’ monthly reports- to the Treasury (accurately) reflected slightly higher or lower balances than would have been reported but for Litvak’s misstatements, such evidence is insufficient to permit a rational jury to find materiality. Indeed, the government has failed to identify any evidence tending to show that these minor variations in the reports’ aggregate balances had the capability to influence a decision of the Treasury.
Third, the government suggests that “[t]he fact that [the] Treasury actually referred the matter to [the special inspector general] for investigation demonstrates that [the] Treasury regarded Litvak’s conduct as significant.”
Our decision in United States v. Rigas, 490 F.3d 208 (2d Cir.2007), supports our conclusion in this case. In Rigas, we evaluated the sufficiency of the evidence in the context of a criminal prosecution for bank fraud, which implicates the same materiality standard applicable here. See supra note 9. We explained that “ ‘relevance’ and ‘materiality’ are not synonymous.” 490 F.3d at 234. Like the limitations placed on the Treasury’s discretion here, see Joint App’x at 321 (“Q. ... [T]he general partner [i.e., the institutional manager of the fund] and the investment managers had all the authority? [Miller]. Correct.”), in Ri-gas, the banks’ discretion was also “limited,” 490 F.3d at 235. In that case, we found certain misstatements material where there was evidence that the banks would have decided to charge a different interest rate had the statements been accurate. See id. at 235-36. However, we found other misstatements, like those here, immaterial even where the government adduced evidence that the banks had received the misstatements and that its staffs had reviewed them, but there was no evidence that the statements were capable of influencing one of the banks’ decisions. See id. at 236. We therefore held that although “[defendants’ misrepresentations certainly concerned a variable that mattered to the banks,” the government must offer sufficient evidence that the misstatements were “capable of influencing a decision that the bank was able to make.” Id. at 234-35.
Here, the government has established that Litvak’s misstatements may have been relevant to the Treasury, and even contrary to its interest in maximizing the PPIFs’ returns. But the evidence also shows that the Treasury’s discretion in the matters at issue was greatly constrained by its status as a limited partner in the PPIFs. See supra note 12 (Miller’s testimony that the Treasury retained “no authority to tell the investment managers” which RMBS to purchase or the prices at which to transact (quoting Joint App’x at 320)). Similarly to Rigas, the exacting circumscription of the Treasury’s role as a decisionmaker highlights the difficulty the government faced in adducing evidence sufficient to identify a decision capable of being influenced.
Therefore, because the government adduced insufficient evidence for a rational jury to conclude that Litvak’s misstatements were reasonably capable of influencing a decision of the Treasury, we reverse the District Court’s judgment of conviction as to the fraud against the United States and making false statements charges (Counts 12-16).
II. Securities Fraud
Litvak raises three primary arguments in respect of the securities fraud counts. First, Litvak contends that the District Court erred in concluding that the evidence was sufficient to support a rational jury’s conclusion that the misrepresentations on which his securities fraud convictions were premised are material. Second, Litvak claims that, in respect of the scien-ter element of these counts, the evidence was insufficient to support the verdict, and the District Court failed adequately to instruct the jury. Third, Litvak challenges the District Court’s exclusion of nearly all of the expert testimony he proffered at trial.
A. Materiality or Immateriality as a Matter of Law
Litvak argues that the misrepresentations he made to counterparties during negotiations for the sale of bonds are immaterial as a matter of law because they did not relate to the bonds’ value (as opposed to their price). Although the District Court did not squarely address this argument, it held that the trial evidence sufficiently supported a finding of materiality.
1.Standard of Review
As explained above, see Part I.A, “a defendant challenging the sufficiency of the evidence bears a heavy burden, as the standard of review is exceedingly deferential.” Brock, 789 F.3d at 63 (internal quotation marks omitted).
2.Governing Law
Determination of materiality under the securities laws is a mixed question of law and fact that the Supreme Court has identified as especially “well suited for jury determination.” United States v. Bilzerian, 926 F.2d 1285, 1298 (2d Cir.) (citing TSC Indus., Inc. v. Northway, Inc., 426 U.S. 438, 450, 96 S.Ct. 2126, 48 L.Ed.2d 757 (1976)), cert. denied, 502 U.S. 813, 112 S.Ct. 63, 116 L.Ed.2d 39 (1991). A misrepresentation is material under Section 10(b) of the Securities Exchange Act and Rule 10b-5 where there is “a substantial likelihood that a reasonable investor would find the ... misrepresentation important in making an investment decision.” United States v. Vilar, 729 F.3d 62, 89 (2d Cir.2013), cert. denied, — U.S. -, 134 S.Ct. 2684, 189 L.Ed.2d 230 (2014). Where the misstatements are “so obviously unimportant to a reasonable investor that reasonable minds could not differ on the question of their importance,” we may find the misstatements immaterial as a matter of law. Wilson v. Merrill Lynch & Co., Inc., 671 F.3d 120, 131 (2d Cir.2011) (internal quotation marks omitted).
3.Materiality Was Properly Reserved for the Jury’s Determination
We conclude that, on the trial record before us, a rational jury could have found that Litvak’s misrepresentations were material. The trial record includes testimony from several representatives of Litvak’s counterparties that his misrepre
In trying to persuade us otherwise, Litvak relies principally upon Feinman v. Dean Witter Reynolds, Inc., 84 F.3d 539 (2d Cir.1996), in which purchasers of securities brought suit against stock brokers with whom they dealt. The purchasers alleged that the brokers charged transaction fees that far exceeded the cost to the firms of the items or services for which the purchasers were ostensibly charged, as described on the trade confirmations (e.g., “handling, postage and insurance if any,” “handling,” “service,” or “processing”). 84 F.3d at 540. The purchasers asserted that these fees were hidden, fixed commissions disguised to circumvent rules prohibiting fixed rates and to prevent customers from negotiating fees. Id.
In affirming the district court’s grant of summary judgment for defendants, we held that “no reasonable investor would have considered it important, in deciding whether or not to buy or sell stock, that a transaction fee of a few dollars might exceed the broker’s actual handling charges.” Id. at 541; see also Id. (“[Rjeasonable minds could not find that an individual ... would be affected ... by knowledge that the broker was pocketing a dollar or two of the fee charged for the transaction.”). We noted that “[e]ach of the defendants’ confirmation slips itemized the amount of the fee; the appellants were never charged more than the amounts reported on these slips.” Id. Thus, “[i]f brokerage firms are slightly inflating the cost of their transaction fees, the- remedy is competition among the firms in the labeling and pricing of their services, not resort to the securities fraud provisions.” Id.
Feinman is readily distinguishable from the case presented. First, the brokers in Feinman did not mislead their customers as to what portion of the total transaction cost was going toward purchasing securities versus the cost of the broker’s involvement. There, the brokers were truthful in stating that a certain portion of the total transaction cost — a specific amount for each broker, up to $4.85 per trade — was charged on behalf of the broker, and that the rest of the transaction’s total cost was used to purchase securities. See id. at 540. “[T]he fees were correctly stated, and the market was not otherwise alleged to have been distorted as a result.” Lit-vak, 30 F.Supp.3d at 150 n. 1 (citing Fein-man, 84 F.3d at 541-42). Unlike the stock transactions in Feinman, “the transaction costs for [Litvak’s] bid list and order trades — as agreed-upon markups or commissions ... — were embedded in the price, and the evidence showed that price was a heavily negotiated term and that the markups Litvak represented himself to be taking were false.” Id. Therefore, unlike in Feinman, Litvak was untruthful about the portion of each transaction’s total cost that would be used to purchase securities and the portion that would be retained by Jef-feries, and in each transaction at issue he falsely understated the latter portion.
Second, the amounts “pocketfed]” by Litvak on behalf of Jefferies in the transactions at issue were substantially larger than “a dollar or two” per transaction, Feinman, 84 F.3d at 541; the difference between the profit his counterparties were led to believe Jefferies yielded and the amount that it actually yielded averaged more than $100,000 per transaction in the twelve transactions at issue (ranging from
Third, the remedy for the behavior described in Feimnan — '“competition among the firms in the labeling and pricing of their services,” 84 F.3d at 541 — is not applicable to Litvak’s behavior. Those he dealt with were unaware that he was taking a larger cut on behalf of Jefferies than he had represented to them. Without knowledge of Litvak’s actions, the financial consequences of negotiations colored by false representations were virtually undis-coverable in the opaque RMBS market. See Litvak, 30 F.Supp.3d at 149 (“As Lit-vak stresses, and as is undisputed by the government, unlike the stock market, the RMBS market is not transparent....”). Until Litvak’s misrepresentations were brought to light by his colleague’s inadvertent email to a counterparty’s representative,
Setting aside Feinman, acceptance of Litvak’s argument is also inconsistent with the “longstanding principle enunciated by the Supreme Court that § 10(b) should be construed not technically and restrictively, but flexibly to effectuate its remedial purposes, and to protect against fraudulent practices, which constantly vary.” Parkcentral Global Hub Ltd. v. Porsche Auto. Holdings SE, 763 F.3d 198, 221 (2d Cir.2014) (per curiam) (internal citations and quotation marks omitted). Finding Section 10(b) inapplicable here, as a matter of law, would require an imper-missibly technical and restrictive construction. There is no dispute that Litvak misrepresented facts related to the securities transactions at issue, and that several of his counterparties’ representatives testified at trial that they considered the misrepresentations meaningful in the course of those transactions and that they or their employers were harmed by Litvak’s misleading course of conduct. In addition, the public interest is implicated by the involvement of the Treasury as a major investor, in several of Litvak’s counterparties in the transactions at issue. Thps, enforcement of Section 10(b) here is consistent with the Supreme Court’s instruction to apply the statute flexibly, see id., and with the statute’s purpose of “remedying] deceptive and manipulative conduct with the potential to harm the public interest or the interests of investors,” id. at 209 (internal quotation marks omitted).
For these reasons, we do not find Lit-vak’s misrepresentations immaterial as a matter of law, and we therefore conclude that the District Court appropriately left
B. Scienter
Litvak contends that the scienter element of Section 10(b) requires proof of “contemplated harm” (or “intent to harm”), that the District Court erred in failing to so instruct the jury, and that the evidence adduced at trial was insufficient to permit a rational jury to find that Litvak had such intent. In ruling on Litvak’s post-trial motions, the District Court reaffirmed its view that “intent to harm” is not an element of securities fraud.
“Liability for