United States v. Cole

Court of Appeals for the Second Circuit·Decided October 27, 2025·No. 23-7566·Published

Opinion

23-7566 United States v. Cole

In the

United States Court of Appeals For the Second Circuit

August Term, 2024

(Argued: January 30, 2025 Decided: October 27, 2025)

Docket No. 23-7566-cr

UNITED STATES OF AMERICA, Appellee,

–v.–

NEIL COLE, AKA SEALED DEFENDANT 1, Defendant-Appellant.

B e f o r e:

JACOBS, CARNEY, and NARDINI, Circuit Judges.

Defendant-Appellant Neil Cole challenges his convictions after a 2022 jury trial in the United States District Court for the Southern District of New York (Ramos, J.) on charges of securities fraud, making false filings with the Securities and Exchange Commission (SEC), and improperly influencing the conduct of audits. He argues that the Double Jeopardy Clause should have precluded the government from trying him for those offenses, because he had been acquitted in a 2021 trial of conspiracy to achieve those same illicit objectives. The District Court erred, in Cole’s view, by rejecting his double jeopardy argument and allowing the second trial to go forward.

The primary question before us is whether the first jury’s verdict acquitting Cole of conspiracy “necessarily decided” factual questions that were essential to the government’s case against Cole at the second trial. If so, the Double Jeopardy Clause’s “issue-preclusion” function should have prohibited Cole’s retrial. See Yeager v. United States, 557 U.S. 110, 119 (2009). Cole urges that, by acquitting him, the first jury necessarily rejected the theory underlying the government’s case on the substantive charges: that Cole inflated the revenue that Iconix reported to investors by making “secret deals” with executives at one of Iconix’s business partners to shift money backand -forth at strategic times. The government offers two narrower interpretations of the jury’s verdict; neither, it says, would preclude the second trial.

After a close review of the trial record, we conclude that each of the government’s theories would have required the first jury to reach an irrational conclusion unsupported by the evidence in the record. We agree with Cole that the acquitting jury must have doubted that Cole made the alleged “secret deals.” Because that theory was essential to Cole’s convictions at the second trial, we REVERSE the judgment of the District Court and REMAND with instructions to vacate Cole’s convictions on the substantive counts and to dismiss the Indictment.

JUSTIN V. RODRIGUEZ, Assistant U.S. Attorney (Andrew Thomas, Danielle R. Sassoon, Assistant U.S.

Attorneys, on the brief) for Damian Williams, United States Attorney for the Southern District of New York, New York, NY, for Appellee United States.

ALEXANDRA A.E. SHAPIRO (Daniel J. O’Neill, Bronwyn C.

Roantree, on the brief), Shapiro Arato Bach LLP, New York, NY, for Defendant-Appellant Neil Cole.

CARNEY, Circuit Judge:

Defendant-Appellant Neil Cole challenges his convictions after a jury trial in the United States District Court for the Southern District of New York (Ramos, J.) on charges of securities fraud, making false filings with the Securities and Exchange

Commission (“SEC”), and improperly influencing the conduct of audits. He argues that the Double Jeopardy Clause precluded the government from trying him for those offenses, because he had been acquitted in an earlier trial of conspiracy to achieve those same illicit objectives.

The Double Jeopardy Clause of the Fifth Amendment provides that no person shall “be subject for the same offense to be twice put in jeopardy of life or limb.” This guarantee is enforced in part through the Clause’s “issue preclusion” function, which prohibits the government from “relitigating any issue that was necessarily decided by a jury’s acquittal in a prior trial.” Yeager v. United States, 557 U.S. 110, 116, 119 (2009). The prohibition works to preserve the finality of the prior jury’s not-guilty verdict and to protect individuals from facing repeated trials for the same conduct.

Cole was tried twice, once in 2021 and again in 2022, for his alleged participation as Chief Executive Officer (“CEO”) of Iconix Brand Group (“Iconix”) in what the government calls an “overpayments-for-givebacks” scheme. In both trials, the government’s theory was that Cole conspired with Iconix’s Chief Operating Officer and executives at one of Iconix’s business partners to inflate the revenues that Iconix reported to investors in 2014. To perpetrate this fraud, Cole allegedly agreed with a business partner that, if the business partner would pay Iconix inflated prices for certain assets (the “overpayments”), Iconix would return the excess amounts at a later date (the “givebacks”). Then, the government said, Cole touted the revenue from the inflated deal prices to investors while omitting mention of the promised givebacks.

A grand jury charged Cole by indictment (the “Indictment”) with conspiracy to achieve three unlawful objectives: securities fraud; submitting false filings to the SEC; and interfering with the conduct of audits. It also charged the conduct underlying those objectives as substantive offenses. In the 2021 trial, the jury acquitted Cole of the conspiracy charge but was unable to reach a unanimous verdict as to any of the

substantive charges. In 2022, over Cole’s objection, the District Court permitted the government to retry Cole on the substantive counts. The second jury, after hearing much of the same evidence as was presented to the first, convicted Cole on each of the substantive counts. Cole now appeals; the District Court has permitted his release on bail pending the outcome of this appeal.

While ordinarily the government may retry a defendant “on any count on which the [original] jury could not agree,” Fed R. Crim. P. 31(b)(3), that rule does not automatically hold if the original jury also acquitted the defendant on related charges. See Yeager, 557 U.S. at 120–21. Rather, under the Double Jeopardy Clause, if the jury “necessarily decided” an issue in the defendant’s favor when it acquitted him, the government is precluded from relitigating that issue. Id. at 120.

Our double jeopardy issue-preclusion analysis proceeds in two steps. To begin, we determine which issues, if any, the first jury’s not-guilty verdict “necessarily decided” in the defendant’s favor. United States v. Mespoulede, 597 F.2d 329, 333–34 (2d Cir. 1979). Next, we “examine how that determination bears on the second case.” Id. at 333. Depending on the issues the first jury decided, we may conclude that its verdict entirely precluded the second trial; that it limited the evidence the government could present in the second trial; or that it had no effect on the second trial at all.

In this appeal, the key question is which, if any, factual questions the first jury’s verdict “necessarily decided” in Cole’s favor. Cole argues that the sole rational explanation for the first jury’s acquittal on the conspiracy count is that it concluded he simply did not make illicit overpayments-for-givebacks deals. The government offers two alternative hypotheses. It proposes first that the jury might have doubted that Cole and his alleged coconspirators actually formed a conspiratorial agreement, without doubting that Cole was guilty of the underlying fraud. Second, it hypothesizes that the jury might have been unable to reach unanimity as to any single criminal object of the

alleged conspiracy, in which event the jury charge directed it to acquit. The District Court was persuaded by the latter theory and on that basis allowed a second trial.

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