Problems with the NFT "Insider Trading" Case

For one thing, it isn't insider trading

Update: on May 3, 2023 Chastain was convicted by a jury of wire fraud and money laundering. I expect he will appeal and make some of the arguments below. The Second Circuit decision should be interesting - stay tuned!

Last month the U.S. Attorney's office for the Southern District of New York announced, with considerable fanfare, that it had brought charges in the “first ever digital asset insider trading scheme.” Prosecutors charged the defendant, Nathaniel Chastain, with using inside information to purchase NFTs that were about to be featured on his employer’s digital marketplace and then resell them at a substantial profit.

The Department of Justice may have been looking to make a splash and send a signal that it is cracking down on crime related to crypto assets. But despite the flashy headlines, this is not an insider trading case. In fact, it’s not clear it should be a criminal case at all.

Facts of the Chastain Case

Non-Fungible Tokens, or “NFTs,” are digital assets that are stored on a blockchain, a digital, centralized ledger of transactions. NFTs are unique digital identifier codes that are associated with a particular digital object, such as a piece of digital art. Although digital images can be reproduced, only the owner of the NFT can be said to own the original digital work, which is considered more valuable – sort of like the difference between owning an original Renoir and a print. The Bored Ape Yacht Club, which features thousands of NFTs of cartoon ape characters, is a well-known example.

Chastain worked at OpenSea, the largest online marketplace for the purchase and sale of NFTs. Beginning in May 2021, OpenSea regularly featured particular NFTs at the top of its website's homepage. Once featured on OpenSea, an NFT usually would rapidly increase in value due to a sudden rise in popularity and demand.

According to the indictment, Chastain was in charge of selecting which NFTs would be featured on OpenSea’s homepage. As OpenSea’s employee, he had an obligation to keep this company information confidential and not exploit it for his own use. But between June and September 2021 he allegedly used this advance knowledge to purchase dozens of NFTs shortly before they were featured on OpenSea. He then sold them at a profit after they were featured and their value rose.

This was not a big-dollar case. The indictment doesn’t specify how much money was involved (which itself is a bit unusual). But in court when he was arraigned, his attorneys claimed that Chastain made only about $65,000 from the scheme.

An interesting aspect of this case is that it appears others in the Crypto-NFT community were the first to figure out what was going on and flag it publicly:

This apparently led OpenSea to fire Chastain and ultimately led to his prosecution. This was possible because what happens on a blockchain is basically public, if you know where to look. (That may have implications for the money laundering charge, as discussed below.)

The Definition of Insider Trading

The very first line of the indictment claims, “This case concerns insider trading in Non-Fungible Tokens or ‘NFTs’ on OpenSea , the largest online marketplace for the purchase and sale of NFTs.” But this is not an insider trading case – at least, not as that term has been used for decades.

Insider trading involves using material, nonpublic information to buy or sell securities in violation of a duty of trust and confidence. Classic or traditional insider trading involves a corporate officer using nonpublic company information to trade shares in her own company, in violation of the duty she owes to her shareholders. Under the “misappropriation theory,” someone who is not a corporate insider but who uses nonpublic information to trade securities in violation of some duty of trust and confidence may also be guilty of insider trading. That duty may arise from trusted relationships such as that between attorney and client or between an employee and an employer.

The Chastain indictment uses some misappropriation theory language that makes the case sound like insider trading. It alleges that Chastain “misappropriated information from his employer, OpenSea, in violation of a duty of trust and confidence that he owed the company, and then used that information to buy and sell the NFTs.”

In an insider trading case the “victim” is the investing public; it’s really a crime against the securities markets. In a true misappropriation theory case the crime is not the breach of a duty (to an employer, in this case) – it’s using the information obtained via that breach to then buy or sell securities. But in this case the government has alleged that the victim is Chastain’s employer, OpenSea. They have charged Chastain with defrauding OpenSea by taking confidential company information and converting it to his own use.

NFTs Are Not Securities - and This Isn’t Insider Trading

Insider trading is a species of securities fraud. It’s a crime against the public securities market that damages investor confidence in those markets. As such, it is typically charged as a violation of the Securities Exchange Act of 1934, specifically 15 U.S.C. § 78j and Rule 10b-5 of the Securities Exchange Commission, which prohibit using any manipulative or deceptive device in connection with the purchase or sale of a security. Insider trading may also be charged under a more recent statute, 18 U.S.C. 1348, which also applies to fraud in connection with publicly-traded securities.

The first requirement of these charges is that the fraud was in connection with the purchase or sale of a “security.” But NFTs generally are not considered securities for purposes of these laws.

NFTs obviously are not publicly-listed securities traded on stock exchanges. But other kinds of investments may also qualify as securities under some circumstances. To determine whether an investment is a security, courts apply what is known as the Howey test, named for an early Supreme Court case. Under that test, characteristics of a security include a common enterprise or horizontal connection among various investors whose fortunes are tied to each other, and a vertical connection between investors and the promoters of the investment, with investors depending on profits that will be derived from the efforts of others. Think of the different shareholders investing in a company as the classic example.

Some crypto assets such as cryptocurrencies could potentially qualify as securities -- that is currently a matter of considerable debate and uncertainty. But NFTs are more like collectibles or artwork. The closest analogy is buying a painting. If I buy an individual work of art, I am not involved in a common enterprise with any other investors. I may hope that it will increase in value, but I’m not depending on the work of others to make that happen. So when I buy my original Renoir, I am not purchasing a “security” under the Howey test.

Whether the NFTs sold on OpenSea qualify as securities might be a legal issue fought out in some future case (although I think the answer is pretty clear), but it’s not going to be an issue in the Chastain case. For despite calling this an “insider trading” prosecution, the government has not alleged that the NFTs Chastain bought and sold were securities.

If we are not talking about securities, then securities fraud charges -- including insider trading -- are not an option. And indeed, prosecutors have not employed the statutes that are used to prosecute insider trading. They did not charge Chastain with violating the Securities Exchange Act or other securities fraud statutes. Instead, they charged him with wire fraud.

A final indication that this is not a securities fraud case is the absence of the Securities Exchange Commission. Typically a securities fraud prosecution would involve investigators and agents from the SEC. Here the case is being pursued only by the FBI, working with the DOJ prosecutors.

In short – this is not an insider trading case, despite the headlines and indictment language to the contrary.

Carpenter v. United States

So if this is not an insider trading case, what kind of case is it? Prosecutors have charged Chastain with defrauding his employer, OpenSea, by taking its confidential business information and using that information for his own benefit. The lead charge is good old wire fraud, 18 U.S.C. § 1343 - the prosecutor's best friend.

There's no allegation that Chastain harmed any of those who purchased the NFTs after he bought them, or that he owed them any kind of duty. And there's no evidence that they were actually harmed, since Chastain's actions didn't drive up the price and presumably they would have bought the featured NFT regardless of who owned it.

At a court hearing, prosecutors alleged that the landmark 1987 Supreme Court case of Carpenter v. United States supports the wire fraud charge. Carpenter involved a reporter at the Wall Street Journal named R. Foster Winans who wrote a column called “Heard on the Street.” Because of the column’s influence, the stock price of companies he discussed could be expected to rise or fall in response to its publication. Winans entered into a scheme with some stockbrokers to buy and sell stocks before the column was published, using his advance knowledge of the column’s contents. They then profited from changes in the stock prices after the column was published.

Unlike Chastain, Winans actually was prosecuted for insider trading under the misappropriation theory, with the government alleging he had misappropriated the column information in violation of his duty to the Journal. That conviction was upheld by the Second Circuit Court of Appeals, but the Supreme Court evenly divided on the question. When that happens the judgment is affirmed but the case has no value as precedent. (The Supreme Court did not fully embrace the misappropriation theory until ten years later in United States v. O’Hagan.)

But as an alternative theory, prosecutors charged Winans with mail and wire fraud. They alleged he had defrauded the Journal of its intangible business property, in the form of the content of the upcoming column. Unlike with the securities fraud charge, in the mail fraud charge the victim was Winans' employer, the Journal. His use of the information in the upcoming columns, prosecutors argued, deprived the Journal of its exclusive right to its confidential business property. The Supreme Court upheld this basis of criminal liability.

Were OpenSea's Business Plans Property?

On its face, the Chastain case does sound a lot like Carpenter. But prosecutors may face one significant hurdle: proving that the information used by Chastain amounted to “property” for purposes of wire fraud.

The Supreme Court has repeatedly held that fraud requires that the defendant deprived the victim of property. Economic or business interests that do not constitute property cannot form the basis of a fraud charge. The Court's trend for the past few decades -- ever since Carpenter, in fact -- has been to limit the reach of the federal fraud statutes by narrowly interpreting this property requirement.

The most recent example was the Court’s 2020 decision in the “Bridgegate” case, Kelly v. United States. There the Court unanimously rejected the government’s theory that the defendants had defrauded the New York/New Jersey Port Authority through a scheme to close traffic lanes on the George Washington Bridge. The Court held that the Port Authority’s power to control access to the bridge, the power of “allocation, exclusion, and control” – although undoubtedly valuable -- was not a property interest for purposes of federal fraud laws.

In Carpenter, Winans had argued that the content of the upcoming column was not a property interest and was too intangible to form the basis of a fraud charge. But the Court rejected that claim, holding that the contents of the column amounted to intangible business property, akin to intellectual property such as patents or copyrights.

Prosecutors will argue that Chastain likewise misappropriated the intangible business property of OpenSea. But it’s not clear that argument will fly. A good definition of “property” is a bundle of rights in something that can be possessed, exclusively enjoyed, and transferred to others. That was true of the contents of the “Heard on the Street” column: the Journal owned it exclusively, controlled it, and could have transferred it -- by selling the content to another publication, for example. The contents of the column were thus intangible property akin to other intangibles such as patents, which can be exclusively enjoyed or licensed or sold to others.

It’s not clear this is true of OpenSea’s plans for its homepage. The internal plan regarding what NFT to feature is not an asset that could be sold or licensed to someone else. That information may be valuable to OpenSea and it may wish to keep it confidential, but that does not mean it is a property interest for purposes of federal fraud laws. Again, misuse of such information might support an insider trading charge -- if we were talking about trading securities. But I'd argue that misuse of internal company plans does not amount to property fraud.

To prove wire fraud, prosecutors will have to prove not merely that Chastain improperly used OpenSea’s private business information, but that he deprived the company of property. I think that will be an uphill battle.

The “Loss of Control” Theory

It’s possible prosecutors intend to rely on the “loss of control” theory to argue that Chastain engaged in fraud. That theory holds that a defendant engages in fraud when he deprives a victim of potentially valuable information that would help the victim decide how to use his assets. The government’s theory might be that Chastain, by deceiving OpenSea and concealing his misuse of its business information, deprived OpenSea of valuable information it otherwise would have use to decide how to control its website, or its business in general.

This “loss of control” theory has been controversial for years. The Second Circuit (where the Southern District of New York is located) has repeatedly approved it, while other circuit courts have disagreed and held it does not amount to fraud. On the final day of its most recent term, the Supreme Court finally granted review in a case, Ciminelli v. United States, where the question presented is whether “loss of control” is a valid fraud theory. In line with the trend over recent decades, I expect the Supreme Court is going to say no. As a result, even if the prosecutors in Chastain were hoping to rely on the theory, that may become impossible.

The Money Laundering Charge

Prosecutors also charged Chastain with one count of money laundering for allegedly using anonymous OpenSea accounts, rather than the account in his own name, to conceal his purchase and sale of various NFTs. The indictment is pretty vague on this point, but it’s not clear that the money laundering charge will hold up either.

I’ve discussed this issue in connection with other prosecutions, including the Varsity Blues case. Just because you use secret bank accounts or take other sneaky steps to try to conceal what you are doing, that does not constitute money laundering. Money laundering requires that the transactions be in criminal proceeds – funds generated by another criminal activity. In other words, in order to launder money, it needs to be “dirty” in the first place. If Chastain purchased NFTs using his salary or other “clean funds,” that would not be money laundering just because he used an anonymous OpenSea account to do it.

Another crypto-related wrinkle in the money laundering charge is that transactions on a blockchain are public – indeed, that is one of blockchain's central features. That explains how others in the crypto community were so easily able to see what Chastain was doing and raise questions about it. Given that, does using other blockchain accounts really amount to an effort to conceal transactions sufficient to support a money laundering charge?

It may be that prosecutors will allege that once Chastain bought and sold the first NFTs, all subsequent purchases and sales used the allegedly criminal proceeds of those early transactions. But that would still leave the issue of whether there was really any concealment, given the public nature of blockchain transactions. Again, the indictment is not very specific so it remains to be seen – but as of now, I have my doubts about the money laundering charge as well.

Employee Misconduct Is Not Necessarily Fraud

The indictment alleges that Chastain had a duty to OpenSea to keep the information about featured NFTs confidential and that he violated that duty. But that merely establishes that he was a bad employee. Employee misconduct is not necessarily criminal. As another court of appeals once held, the federal fraud statutes are not supposed to serve as a “draconian personnel regulation.” Chastain may have deserved to lose his job and to be treated with disdain in the crypto community. That doesn't mean he deserves to go to jail.

I’ll be watching to see how this case unfolds. But if federal prosecutors were trying to show that they are cracking down on crypto-related crime, they picked a pretty lame showcase.

Update: After this post was written, on July 21 the same U.S. Attorney's Office announced the first "insider trading" case involving cryptocurrency. Prosecutors charged a former Coinbase employee, Ishan Wahi, and two co-defendants with trading on information about which tokens would be listed on Coinbase's exchange. This case has the same issues discussed above: although prosecutors called it "insider trading," it really isn't. Prosecutors have charged wire fraud, not securities fraud, and will face the same hurdles. In Wahi, the SEC has also filed a civil complaint, alleging that the tokens traded do qualify as "securities." But in the criminal case, just as in Chastain, prosecutors have not charged securities fraud and have not alleged that the cryptocurrencies were securities.

Update: On October 21, 2022, the judge in Chastain's case denied his motion to dismiss, which had made essentially the same points I discussed above. The judge agreed the arguments have "some force," but said they were arguments for the jury. The judge also agreed that the lead charge is property fraud, not true "insider trading," but that would not justify dismissing the indictment. If the judge concludes the term is misleading, he may bar the government from using it at trial and strike it from the indictment.