United States v. Chastain

CourtCourt of Appeals for the Second Circuit
DecidedJuly 31, 2025
Docket23-7038
StatusPublished

This text of United States v. Chastain (United States v. Chastain) is published on Counsel Stack Legal Research, covering Court of Appeals for the Second Circuit primary law. Counsel Stack provides free access to over 12 million legal documents including statutes, case law, regulations, and constitutions.

Bluebook
United States v. Chastain, (2d Cir. 2025).

Opinion

23-7038 United States v. Chastain

In the United States Court of Appeals FOR THE SECOND CIRCUIT

AUGUST TERM 2024 No. 23-7038

UNITED STATES OF AMERICA, Appellee,

v.

NATHANIEL CHASTAIN, Defendant-Appellant. *

On Appeal from the United States District Court for the Southern District of New York

ARGUED: NOVEMBER 19, 2024 DECIDED: JULY 31, 2025

Before: CABRANES, WESLEY, and MENASHI, Circuit Judges.

Nathaniel Chastain appeals his judgment of conviction for wire fraud and money laundering. A jury found him guilty of those offenses based on trades he made while employed at the online NFT marketplace OpenSea. Chastain argues that the district court erred by

* The Clerk of Court is directed to amend the caption as set forth above. instructing the jury that it could find him guilty of defrauding OpenSea of its property if he misappropriated an intangible interest unconnected to traditional property rights. He maintains that this error affected the jury’s decision. We agree. We reject Chastain’s additional arguments that the district court erred by preventing him from introducing evidence at trial. We vacate the judgment of conviction for wire fraud and money laundering and remand for further proceedings consistent with this opinion.

Judge Cabranes concurs in part and dissents in part in a separate opinion.

ALEXANDRA A.E. SHAPIRO, Shapiro Arato Bach LLP, New York, NY (Jason A. Driscoll, Shapiro Arato Bach LLP, New York, NY; David I. Miller, Daniel P. Filor, Greenberg Traurig, LLP, New York, NY, on the brief), for Defendant-Appellant.

NICOLAS ROOS, Assistant United States Attorney (Thomas S. Burnett, Allison C. Nichols, Danielle R. Sassoon, Assistant United States Attorneys, on the brief), for Damian Williams, United States Attorney for the Southern District of New York, New York, NY, for Appellee.

MENASHI, Circuit Judge:

Nathaniel Chastain appeals his judgment of conviction for wire fraud in violation of 18 U.S.C. § 1343 and for money laundering in violation of 18 U.S.C. § 1956. A jury found Chastain guilty of those offenses based on trades he made while employed at OpenSea, an online marketplace for non-fungible tokens (“NFTs”). As head of 2 product, Chastain selected the NFTs that the company would feature in a section of its website. When an NFT was featured, its value increased. Chastain would purchase an NFT before it was featured and sell it afterward for a profit. He made about $57,000.

The district court instructed the jury that Chastain’s decision about which NFT to feature was OpenSea’s property even if that information lacked commercial value to OpenSea. It further explained that the jury could find that Chastain engaged in a scheme to defraud if he “conducted himself in a manner that departed from traditional notions of fundamental honesty and fair play in the general and business life of society.” App’x 411.

Chastain argues that the instructions were erroneous because the jury could have convicted Chastain of fraud based on unethical business dealings even if he did not intrude on anything resembling a traditional property interest of OpenSea. We agree.

We further conclude that the error cannot be considered harmless. The jury heard testimony that OpenSea could have experienced reputational harm if its users learned about Chastain’s conduct, but the evidence also indicated that the featured NFT information was so tangential to OpenSea’s business that failing to maintain the confidentiality of the featured NFTs would not affect users’ attitudes toward the platform. A note from the jury suggested that it believed that OpenSea did not view the featured NFT information as confidential but that Chastain acted unethically by trading on the information. Under these circumstances, we cannot say that the jury would have reached the same verdict if it had been properly instructed that fraud requires the appropriation of a property interest rather than unprofessional business conduct.

3 Chastain additionally contends that the district court abused its discretion by excluding evidence relating to (1) whether other OpenSea employees viewed the featured NFT information as confidential, (2) whether OpenSea made changes to the template it used to create the confidentiality agreement that Chastain signed, and (3) the trading history of one of OpenSea’s co-founders. We conclude that the district court did not abuse its discretion.

We vacate the judgment of conviction for wire fraud and money laundering, and we remand for further proceedings consistent with this opinion.

BACKGROUND

OpenSea is an online marketplace for buying and selling NFTs. An NFT is a “unique digital artifact” that “can be bought and sold on the blockchain.” App’x 167. OpenSea itself does not buy or sell any NFTs that are traded on its platform. Instead, the company collects a fee of two-and-a-half percent for each transaction on the platform. In 2021, OpenSea added a section to its website that would promote user interest by highlighting specific NFTs. When an NFT was featured, the publicity typically led its price to increase. OpenSea did not receive payments from the creators of NFTs featured on the website. Nor did OpenSea engage in any trades of featured NFTs. Instead, for each transaction involving a featured NFT, OpenSea received its standard fee of two-and-a-half percent.

I

Chastain was the first head of product at OpenSea. In that role, he was “responsible for evaluating current and new features, to figure out how well they were doing.” Id. at 186. He obtained “feedback” and conducted “user interviews” about the features, and he considered “new changes” that could “improve the site. He would

4 help organize engineers to work on these projects and designers.” Id. He also selected the NFTs that the website would feature.

Chastain purchased approximately fifteen NFTs that were then featured on the website. Chastain generally purchased and sold the featured NFTs using anonymous accounts. For each trade, he transferred cryptocurrency from his personal account into an anonymous account that he used to purchase the NFT. The anonymous account would sell the NFT after it was featured, and Chastain transferred the proceeds back into his personal account. He made about $57,000.

Chastain did not always use anonymous accounts. On August 2, 2021, an OpenSea user noticed that Chastain had used his personal account to purchase an NFT before it was featured. The user posted to Twitter that it “[l]ooks like Nate from OS had the jump on everyone else,” adding an emoji of two eyeballs. Id. at 593. Chastain responded to the post that he “just wanted to secure one of these [NFTs] before they all disappeared tbh.” Id. At this point, no one at OpenSea told Chastain to stop purchasing featured NFTs.

On September 14, 2021, another OpenSea user posted about Chastain’s trading, this time tagging OpenSea:

Hey @opensea why does it appear @natechastain has a few secret wallets that appears to buy your front page drops before they are listed, then sells them shortly after the front-page-hype spike for profits, and then tumbles them back to his main wallet … ? Id. at 594. The next day, OpenSea asked Chastain to resign. After his resignation, Chastain maintained friendly social relationships with OpenSea’s co-founders. See id. at 238, 325.

5 II

On May 31, 2022, the government filed a two-count indictment. Count One charged Chastain with wire fraud in violation of 18 U.S.C. § 1343.

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United States v. Chastain, Counsel Stack Legal Research, https://law.counselstack.com/opinion/united-states-v-chastain-ca2-2025.