You might not think of Jon Gruden’s long-running legal battle against the NFL as a free speech case, but the league certainly does. It’s arguably the strangest First Amendment dispute still working its way through the courts: whether Roger Goodell cost Gruden his job as head coach of the Las Vegas Raiders by leaking his racist, misogynistic, and homophobic emails to The Wall Street Journal and The New York Times—and whether, if the NFL actually did that, they were exercising their right to free speech.

Remarkably, that’s where this litigation now sits. Gruden alleges that NFL executives intentionally disclosed those offensive emails, triggering his resignation and costing him tens of millions in salary and endorsements. He already beat back the league’s push to force the dispute into arbitration. Now the $150 million tortious interference case is in discovery, on track for a May 2027 trial.

One skirmish along the way, though, has slipped almost entirely under the radar. After losing on arbitration, the NFL pivoted to Nevada’s anti-SLAPP statute, arguing that Gruden’s suit targeted truthful speech protected by the First Amendment and should have been tossed outright. District Judge Joe Hardy wasn’t persuaded—he rejected the motion as untimely and, more importantly, found that Gruden had shown a probability of prevailing on the merits. The NFL is now effectively asking the Nevada Supreme Court for an instant replay. (The league is represented by Brad Karp, the former Paul Weiss chairman who stepped down last year after his own correspondence with Jeffrey Epstein surfaced.)

In a recent appellate brief, Karp argued that Gruden’s emails concerned a matter of undeniable public importance. At the time they surfaced, he noted, the NFL was under intense scrutiny over workplace culture during its investigation into the Daniel Snyder–owned Washington franchise, while the league had spent years publicly championing anti-discrimination and diversity initiatives. The fact that virtually every major news organization covered the emails, he argued, underscored their public significance. If the NFL disclosed them, Karp went on, those disclosures were “good faith communications” on an issue of public concern in a public forum—precisely the sort of speech that Nevada’s anti-SLAPP statute was designed to protect. And the NFL, he added, shouldn’t lose the benefit of that protection simply because it first tried to send the dispute to arbitration.

Gruden responded that the NFL was fighting the wrong case. His lawsuit, he said, isn’t simply about leaked emails, but rather the alleged campaign to force the Raiders to fire him—privately pressuring the organization, supplying it with materials from the Washington investigation, and dangling the threat of additional disclosures until he resigned. And as for the NFL’s claim that the emails themselves were a matter of public concern because they addressed race, gender, and sexual orientation, Gruden’s lawyers offered a provocative rejoinder in their own brief filed just last week: “Before the NFL Parties’ publication of Gruden’s emails, there was no public interest in his private emails with friends,” they wrote. “This standard would mean any email between private individuals about these topics could become a matter of public concern.” In other words, the First Amendment can’t turn a leak into protected speech.

Gruden has a point. The ugliness of his emails seems to have obscured his unusual but consequential claim that the NFL weaponized confidential investigative material collected for one purpose to achieve another. After all, the Gruden emails surfaced from a totally separate scandal. The NFL opened a confidential investigation into workplace misconduct within Washington’s football franchise, then allegedly plucked a handful of Gruden’s emails from roughly 650,000 documents and used them to bring down one of Goodell’s most outspoken critics.

Right now, the NBA has retained Wachtell Lipton to investigate whether Steve Ballmer’s Los Angeles Clippers circumvented the salary cap by arranging a no-show endorsement deal for Kawhi Leonard. Imagine if, after that investigation concluded, Adam Silver combed through the files, found embarrassing emails involving an entirely different owner, and selectively leaked them to force that owner into line. That, in essence, is Gruden’s theory.

Viewed through that lens, the case looks less like a dispute over offensive speech than an alleged abuse of investigative power. The leak becomes the means rather than the wrong itself, and motive assumes far greater importance. That’s one reason Judge Hardy concluded that Gruden had shown enough to proceed. Even if Karp persuades the Nevada Supreme Court that the anti-SLAPP motion should have been considered despite its extraordinary lateness, the league still faces the tough task of convincing the justices that Gruden stands little shot of ultimately prevailing.

As for the merits, however, the NFL has said that Gruden still can’t establish that the league was actually responsible for leaking his emails to the press. For his part, though, Gruden responded that the league was dodging half the case—it has never really denied communicating with the Raiders or trying to influence the team’s decision. And when it comes to the alleged leaks themselves, his lawyers posed a more conceptual objection: How could the NFL simultaneously deny making the disclosures while also claiming immunity for them? As Gruden put it, the league can’t have it both ways—disclaiming responsibility while claiming protection for the same act.

The Nevada Supreme Court may ultimately resolve this appeal on procedural grounds. But the underlying issue isn’t going away. Professional sports leagues increasingly rely on sprawling internal investigations that collect enormous volumes of confidential emails, texts, and other communications. The NFL now finds itself invoking a statute designed to protect speakers from frivolous lawsuits that chill First Amendment activity. Gruden, by contrast, points to a darker implication: If organizations can later repurpose those confidential investigative materials to satisfy ulterior motives, the documents become repositories of future leverage rather than tools for uncovering misconduct. Whatever happens to his lawsuit, that’s a tension with a much longer shelf life than Gruden himself.

Thanks, Eriq. See you all tomorrow.

John