Donald Trump’s latest legal tantrum—his $10 billion defamation suit against The Wall Street Journal, for its piece about a Jeffrey Epstein birthday card that the president swears he never wrote—may end up backfiring, triggering the exposure that Trump has spent years trying to avoid. As defamation suits go, this one isn’t particularly strong. If it gets past early hurdles, however, it could lead to sustained, sworn scrutiny of his relationship with the convicted sex offender who traveled in the same Upper East Side and Palm Beach circles.

The alleged note—equal parts crude and juvenile—wished Epstein “another wonderful secret” and featured a sketch of a naked woman. Trump has called it a fabrication, but he’s been conspicuously vague about what exactly in the article defamed him. The suggestion that he and Epstein were once on friendly terms? That’s well-trodden territory, supported by photos, quotes, and years of media coverage. The scribbled birthday sentiment? Trump has insisted that it’s bogus, but he hasn’t credibly proven so, or demonstrated that the newspaper knew it was a phony. If his argument is that the piece falsely implies criminal complicity, he hasn’t connected the dots.

Lawyers for Rupert Murdoch, who owns the Journal via his News Corp, will pounce on all of it: the ambiguities, the absence of defamatory sting, the lack of “actual malice,” and, perhaps most glaringly under Florida law, Trump’s failure to provide the required five-day notice before filing suit. All this will be reviewed by U.S. District Court Judge Darrin Gayles, who was appointed by Barack Obama in 2014. This time around, there’s no Aileen Cannon, the Trump appointee who helped him skate the Jack Smith charges.

Still, Florida courts have been receptive to Trump-adjacent libel claims. Take his suit against ABC News over George Stephanopoulos’s on-air assertion that Trump had been found liable for raping writer E. Jean Carroll. That survived a motion to dismiss, and ABC owner Disney then settled for $16 million. Or consider the president’s libel case against members of the Pulitzer board for rewarding Russia election interference reporting. That case is still ongoing, to the puzzlement of many, and has received a rubber stamp of approval from a Florida appeals court.

Then there’s Laura Loomer’s bizarre, but still active, lawsuit against Bill Maher for joking on HBO that she slept with Trump—a smear she alleges cost her a job in the administration. Maher’s lawyers have argued that no reasonable viewer would interpret the segment as factual. But the judge, noting that the studio audience groaned, instead of laughed, let it proceed. The litigation has since devolved into sideshow antics, including taunts of public depositions and allegations that Loomer is using discovery as a fundraising tool.

Whether or not Trump’s case against the Journal ends up following a similar trajectory, he’s already expressing a wish to depose Murdoch. The president’s legal team could seize on the mogul’s advanced age, 94, to press for an expedited examination of his dealings with WSJ editors and executives. For their part, the defendants might welcome discovery, especially if it involves Epstein-related D.O.J. files, or puts Trump under oath about his history with the late sex offender.

Remember, much of what the public knows about Epstein emerged from a court case—specifically, Epstein accuser Virginia Giuffre’s defamation lawsuit against Ghislaine Maxwell in 2015. Journalists, led by the Miami Herald’s Julie K. Brown, fought to unseal those records, resulting in a media firestorm and renewed federal attention. While Giuffre’s defamation case was settled, the spotlight ultimately led to the criminal sex trafficking charges against Epstein and Maxwell. (Maxwell is serving 20 years in federal prison; Epstein died by suicide before he was tried.)

One wrinkle in Trump’s suit against the Journal is whether the publication can invoke Florida’s anti-SLAPP statute, which is designed to shield free speech by dispatching flimsy lawsuits early and, ideally, sending the loser home with the legal bill. Had Trump filed his suit against the Journal in California, for example, the state’s strong anti-SLAPP protections would have kicked in immediately, allowing the newspaper to seek a swift exit and fee recovery. Florida is murkier.

If it strikes you as odd that federal courts handle lawsuits differently depending on geography, you’re not alone. There’s a Trumpian backstory here. A little more than a decade ago, while burnishing his Apprentice persona and suing anything that moved, Trump fought allegations that Trump University was a scam. In a bid to change the narrative, he filed a defamation suit against a disgruntled student. The claim was tossed, and the Ninth Circuit affirmed. But a concurring opinion from Alex Kozinski, then the Ninth Circuit’s chief judge, left a mark. Kozinski fumed that California’s anti-SLAPP statute had carved an “ugly gash” through the orderly sequence of discovery, summary judgment, and trial envisioned by the federal rules. He couldn’t persuade his colleagues to banish state anti-SLAPP laws from federal courts entirely, but he did plant the seeds of skepticism among the Federalist Society faithful.

In the years that followed, conservative judges around the country increasingly declared federal courts an anti-anti-SLAPP zone, curbing the reach of states’ free-speech statutes in federal litigation.

These days, Trump remains entangled in more lawsuits than a class-action lawyer’s Christmas list. Among them is a defamation case he’s defending, stemming from his remarks about the so-called Central Park Five during his debate last September with Kamala Harris, who’d reminded viewers that Trump had taken out a full-page newspaper ad calling for the execution of the Black and Latino teenagers for allegedly raping and nearly killing a jogger. In the debate, Trump falsely claimed that the men had pleaded guilty, and “ultimately killed a person.” The five men, who were fully exonerated in 2002, filed a defamation lawsuit against Trump after the debate. In that case, Trump’s lawyers are now arguing for dismissal, saying the president was merely evoking his mindset from the time he’d bought the newspaper ads, and that any misstatements during the debate fell under the forgiving umbrella of “substantial truth,” because the teens initially confessed, albeit under duress.

The problem for Trump here is that federal courts don’t let judges wade into factual disputes at the motion-to-dismiss stage. And so, in April, U.S. District Judge Wendy Beetlestone ruled she couldn’t address the “substantial truth” defense, and let the plaintiffs amend their complaint to beef up the defamation claims.

Trump then invoked Pennsylvania’s anti-SLAPP law—the presidential debate took place in Philadelphia—hoping it might get the judge to toss the case. No luck. A few weeks ago, Beetlestone ruled that Pennsylvania’s anti-SLAPP statute “collides” with federal procedural rules, tipping her hat to Kozinski’s old concurrence in the Trump University case. Trump has launched an appeal.

The irony is rich. Trump now finds himself championing anti-SLAPP protections in federal court—a maneuver that, if successful, could make it easier to fend off the kind of libel suit he’s so fond of filing. It’s a development that First Amendment advocates and media lawyers will quietly relish as the dispute makes its way to the Third Circuit Court of Appeals—and perhaps even back with amicus briefs.

Of course, Trump’s newfound love affair with anti-SLAPP statutes is purely transactional. He’ll invoke federal rules one day, state procedures the next—whichever tool happens to be most useful. A month ago, he tried, unsuccessfully, to withdraw his lawsuit against The Des Moines Register and pollster Ann Selzer a day before Iowa’s new anti-SLAPP law took effect. And one has to wonder whether his lawsuit against CBS over that 60 Minutes edit of the Harris interview would have seen daylight if Texas federal courts were more welcoming of the state’s particularly aggressive anti-SLAPP regime, and Trump was potentially on the hook for Shari Redstone’s legal tab.

Still, irony aside, it’s probably a good thing that Trump is defending the notion that judges should be able to wield state anti-SLAPP laws in federal court to toss defamation claims when appropriate. Insiders have long speculated that the Supreme Court has been waiting for the right case to resolve the messy circuit split over anti-SLAPP’s place in federal court. Will it be the Central Park Five case? Or the WSJ suit over the Epstein birthday letter? Stranger things have made it onto the docket.

Thanks, Eriq. Super interesting. I’ll see everyone on Thursday evening.

Matt