Happy Monday, I’m Eriq Gardner.

Welcome back to The Rainmaker, my private newsletter focused on the legal maneuvering inside Hollywood, Silicon Valley, Washington, and Wall Street.

This week, as we all wait for whatever is in that affidavit behind the F.B.I. raid of Mar-a-Lago, I reveal the 10 crypto cases that everyone should be following—if only for the Hulu adaptations that will inevitably drop a few years from now. Plus updates on the Supreme Court’s Andy Warhol dilemma, Ron DeSantis’s “Stop Woke” legislation, and why that lawyer you’re consulting may be ratting you out to the feds.

But first…

—California Governor Gavin Newsom has appointed Jaime Crook as chief counsel of the state’s top civil rights agency. It’s an important role given how aggressive the Department of Fair Employment and Housing has been in recent years. Ongoing legal battles include alleged sexual harassment at Activision Blizzard and at Disney, plus alleged racial discrimination at Tesla.

—The antitrust trial over Random House’s purchase of Simon & Schuster has wrapped after closing arguments on Friday. The trial focused on book advances at the top of the market, which caused defense lawyer Daniel Petrocelli to attack the government’s market definition as well as the merger’s predicted impact. Leaning on testimony from authors including Stephen King, the government argued that consolidation would give this mega-publisher too much power in the labor market. Both sides will now file post-trial briefs. A decision from Judge Florence Pan is expected in autumn.

—As the Supreme Court gets ready to revisit how to determine copyright fair use in an Oct. 12 argument over Andy Warhol’s work, the justices have received a new round of amicus briefs. Those sticking up for photographer Lynn Goldsmith, who is in court with Warhol’s heirs and now aims to preserve her Second Circuit advantage in the closely followed case, include the Recording Industry Association of America, the Screen Actors Guild, the Association of American Publishers, and perhaps most significantly, the Biden administration.

Yes, the U.S. government has filed a brief that asks the justices to reject the proposition that a new “transformative” work was created when Warhol screen-printed a copy of Goldsmith’s photo of Prince just because the pop art icon may have contributed new meaning to the photographer’s image. Both the government and Hollywood seem to be implicitly worried that expanding the scope of what is considered fair use could tread on rights traditionally reserved for copyright holders. For example, the government points out that book-to-film adaptations “often introduce new meanings or messages, but that has never been viewed as an independently sufficient justification for unauthorized copying.” Solicitor General Elizabeth Prelogar has requested time to participate in the oral arguments.

Let me state at the outset that I’ve never owned any crypto assets or digital art on the blockchain, and I’ll readily admit I’ve never participated in a DAO (unlike my partner Baratunde Thurston, who tried to buy a piece of the U.S. Constitution). Nor am I entirely convinced of the value of decentralized finance, or DeFi—at least from an investment standpoint. What appears to some crypto fans as a long overdue effort to reclaim power from Wall Street banks and the Federal Reserve seems to me to be an enterprise transferring power to the techno-elite. And I’m not sure I trust Tyler and Cameron Winklevoss more than Jamie Dimon.

But from a non-investment standpoint, I can also identify innovation when I see it, from DeFi to “Web 3.0,” and particularly in the legal arena where so many questions pertaining to this digital frontier—Who owns the rights to an NFT character? Is Kim Kardashian liable for pumping the value of a digital token?—are being actively litigated. Usually, I have a pretty decent intuition for legal outcomes. But not with these ten cases. Well, make that nine cases where anything could happen. I would not bet a single bitcoin against Kim K.

Securities and Exchange Commission v. Ripple Labs Inc: Speaking of crypto assets as alleged unregistered securities, this is the test case—the one that could determine whether the federal agency that oversees public markets plays a strong regulatory role in crypto moving forward. The S.E.C. accuses Ripple and two executives of conducting an illegal $1.3 billion offering, and this proceeding has gotten so hot that the judge recently allowed the government to keep the identity of its experts a secret for now. Summary judgment motions are due next month. Meanwhile, the S.E.C. is pursuing other companies and individuals for failing to register securities, such as those behind the Dragon token in a complaint filed this past week.

Dan Carman v. Janet Yellen: When Congress passed a big infrastructure law last year, lawmakers tucked in a provision that requires crypto exchanges like Coinbase to notify the I.R.S. of high-value transactions. The plaintiffs in this Kentucky case claim that this reporting provision amounts to an unreasonable search under the Fourth Amendment and ultimately an unconstitutional violation of one’s privacy. The dispute could eventually become catnip for the Supreme Court, which may also be intrigued by a First Circuit opinion last week in Harper v. Rettig concerning how the I.R.S. obtained records about an attorney’s crypto holdings. In the meantime, the Biden administration must respond by November 7.

Free Holdings v. Kevin McCoy: The history and terminology surrounding non-fungible tokens will be explored in this complex slander of title lawsuit focused on how the auction house Sotheby’s marketed the “first NFT”: Kevin McCoy’s Quantum, a 2014 blockchain-recorded artwork which sold for $1.472 million last year. The plaintiff (a Canadian holding company) alleges being the rightful owner of McCoy’s first NFT after the artist failed to renew his registration. The suit focuses on whether Sotheby’s and McCoy offered a “false narrative” about how Quantum was “burned” or “removed” from one blockchain and then re-minted on another.

Miramax v. Quentin Tarantino: How should Hollywood think of NFTs and fit them into its traditional entertainment framework? Famed movie director Quentin Tarantino insists he held onto rights to publish the Pulp Fiction screenplay and can sell NFTs derived from that screenplay while Miramax argues that Tarantino’s reserved rights are pretty limited and don’t cover this. A judge is set to rule soon, and while there’s been some buzz of a potential settlement thanks to Miramax reporting “progress” in a recent filing, an insider tells me a deal isn’t actually imminent.

Nike v. StockX: The defendant is an online sneaker marketplace selling NFTs of Nike shoes. The twist, according to StockX, is that the NFT corresponds to a physical shoe in a warehouse and is “effectively a claim ticket” to the stored item. Nike sees intellectual property infringement. StockX responds that what it’s doing is protected as nominative fair use, which allows certain lawful references to trademarks, and the first-sale doctrine, which allows the owner of a particular copy of a work to sell that copy. The parties are in the midst of the discovery phase of this case.

Celsius Network bankruptcy: If crypto is ever to achieve long-term trust and stability, a successful restructuring where creditors feel taken care of is probably necessary. That’s where Celsius, the much-ballyhooed and now-bankrupt crypto bank, comes into play. Celsius customers transferred their crypto assets, earned rewards, and took out loans using crypto as collateral. But in July, the company filed for Chapter 11, leading customers to worry what would happen to the bank’s $5 billion in lost assets. The debtor continues to operate, however, and has at least a few months before cash runs out. Meanwhile, a U.S. trustee recently cited the “relatively new, purposefully opaque, and, at best, loosely regulated” crypto market while calling for the appointment of an independent examiner to investigate Celsius and report on what went wrong.

In Re Ethereummax Investor Litigation: When crypto assets implode, should the celebrities who hyped them face any consequences? This particular case aims to apply legal blame to Kim Kardashian, Floyd Mayweather, Jr., and Paul Pierce for artificially inflating the price of EMAX tokens. Kardashian recently moved to dismiss this investor class action on the basis, among other things, that plaintiffs failed to adequately show EMAX buyers were inspired by her Instagram posts to purchase the tokens.

Christian Sarcuni, et al., v. bZx DAO, et. al: There’s remarkably little jurisprudence regarding decentralized autonomous organizations, or DAOs, in which a digital token affords certain voting rights taken by the collective. The bZx DAO, for instance, governed a protocol that allowed users to trade in crypto assets on margin, but became the target of angry users who lost their funds to hackers. Now a big question is whether bZx DAO token holders are “partners'' jointly liable for alleged negligence or whether these strangers are nothing of the sort and shielded from legal responsibility. A California judge is currently hearing arguments on whether the plaintiffs have properly stated a claim.

USA v. Lichtenstein: Finally, there’s this criminal case, which seems destined for adaptation into a future movie or TV show. Heather Morgan and Ilya Lichtenstein were a New York couple who dabbled in tech entrepreneurship, writing, rapping—yes, really—and being social influencers. In other words, they were pretty typical millennials. But according to the government, they were also quietly trying to launder over 120,000 bitcoin stolen in a 2016 hack. The value of that bitcoin had climbed from hundreds of thousands of dollars to around $4 billion at the time they were arrested—making their alleged heist technically the biggest in the country’s history. F.B.I. agents found tens of thousands in foreign currencies, hollowed out books, dozens of tablet computers, and a burner phone when raiding their apartment. Their lawyers say the money laundering accusations are “predicated on a series of circumstantial inferences and assumptions drawn from a complex web of convoluted blockchain and cryptocurrency tracing assertions.” The trial, if there’s no plea deal, should be a fascinating one.

DeSantis’s next big legal battle will likely be against Andrew Warren, the Tampa state attorney whom the governor fired after he declared that he would not prosecute anti-abortion laws in the wake of the Supreme Court’s Dobbs decision. Warren is now suing over his termination, alleging that DeSantis’s move violates the First Amendment’s prohibition against government officials subjecting individuals to retaliatory actions for engaging in protected speech. Here’s the complaint.

—The other week, I explained how SAG-AFTRA was using a favorable political climate in California as leverage in negotiations with producers over contracts that lock actors into exclusive gigs. The guild first got Netflix to agree to changes including a monthslong conflict-free window for series regulars to take additional movie and TV work, and now it’s also convinced the Alliance of Motion Picture and Television Producers (Disney, Warner Bros., Universal, Paramount, Sony…) to agree to a similar arrangement. SAG-AFTRA’s board approved the deal on Saturday.

—The National Football League won’t have to go to a federal court with Deshaun Watson after all. The league and the quarterback have agreed to an eleven-game suspension for sexual misconduct. Observers can debate whether the star got off easy for accusations from several dozen women, but the case will become precedent for the N.F.L. handing out more severe penalties moving forward.

—What’s the difference between life insurance and an illegal wager on someone’s life? Depends who’s making the investment and bearing the risk. See why the Seventh Circuit voided an insurance policy this past week.

According to Kovner’s response, the Department of Justice looked for a court order approving its use of an attorney as a confidential source in a money laundering investigation. Of course, there were a couple problems with the plan: First, communications between attorneys and their clients are privileged, unless the attorney is an active participant in the crime. Second, attorneys are not supposed to behave dishonestly, at least according to rules for professional conduct. Alas, if law enforcement used the attorney as a tipster, they couldn’t be sure that the evidence would later be admissible.

So federal prosecutors asked Kovner to rule that attorney-client privilege wouldn’t apply thanks to the crime-fraud exception. Additionally, federal prosecutors took the position that helping them — even if it meant lying — couldn’t be ethically unsound. Kovner didn’t accept or reject these positions, but she declined to issue “advisory rulings” on what’s in and out of bounds. The judge concluded she lacks the authority to do that.

Now the government wants this whole matter sealed and hidden away. The motion to seal is itself non-public so I can’t say for sure whether prosecutors are embarrassed at their defeat, or more likely, still have designs on using attorneys as confidential sources and don’t want people to know about their methods.