Jon Gruden’s Lawsuit Against the NFL Hits $150 Million Mark as Legal Battle Intensifies
Jon Gruden’s legal fight with the NFL and Commissioner Roger Goodell isn’t going away anytime soon - and according to new court filings, the former Raiders and Buccaneers head coach believes the damage done to his career and reputation is worth more than $150 million.
In a Case Conference Report filed on February 5, Gruden’s legal team laid out the scope of what they say he’s lost since his resignation from the Raiders - and it’s a staggering list. Gruden is seeking compensation for the loss of his job, missed future opportunities in coaching and broadcasting, the value of his terminated contract, lost sponsorships, reputational harm, and mounting legal costs, including expert and attorney fees. All told, the number exceeds $150 million.
This all stems from Gruden’s abrupt departure from the Raiders, which came after emails he sent while working at ESPN were made public in reports from the Wall Street Journal and New York Times. The emails surfaced during the NFL’s investigation into the Washington Commanders and former owner Daniel Snyder. Gruden’s camp has consistently argued that the emails were selectively leaked to force him out - and they’re aiming to prove it in court.
The Case Conference Report was filed following an early case conference that the NFL declined to attend. According to the report, the league is holding off on participating in discovery while it appeals a previous ruling that denied its motion to dismiss the case under Nevada’s anti-SLAPP statute - a law designed to prevent frivolous lawsuits aimed at stifling free speech.
But even with that procedural delay, Gruden’s legal team is pressing forward. The report includes a list of potential witnesses they may call, and it’s a who’s who of NFL power brokers.
Among those named: Commissioner Roger Goodell, former NFL general counsel Jeff Pash, league spokesman Brian McCarthy, Cowboys owner Jerry Jones, Patriots owner Robert Kraft, Raiders owner Mark Davis, and former Raiders executive Dan Ventrelle. Also listed are individuals from the Paul Weiss and Reed Smith law firms, attorney Beth Wilkinson (who led the Commanders investigation), Roc Nation’s Desiree Perez, and former NFLPA executive director DeMaurice Smith - along with Gruden himself.
Now, it’s worth noting that just because these names appear in the report doesn’t mean depositions are imminent. The filing doesn’t confirm whether Gruden’s attorneys will seek to depose all or any of them, nor does it mention any current efforts to compel testimony.
The report also highlights several NFL teams that could hold relevant information: the Commanders, Raiders, Cowboys, Patriots, Seahawks, Giants, Jets, and Dolphins. Interestingly, the report doesn’t name any journalists from the Wall Street Journal or New York Times as potential witnesses or sources of information.
Gruden’s team is also pushing for immediate access to a trove of documents - including all 650,000 materials collected during Wilkinson’s investigation into the Commanders. One item in particular stands out: a so-called “‘Blackmail PowerPoint’” that was allegedly presented by Snyder and/or the Reed Smith firm to NFL officials. According to the report, that presentation contains communications involving both Goodell and Pash.
As of now, there have been no settlement talks, according to the report. And while it’s unclear whether the NFL will take this all the way to the U.S. Supreme Court in an attempt to force arbitration - a process that would keep the case behind closed doors - that possibility is still on the table.
This legal battle has already stretched on for more than four years, largely bogged down by procedural fights over whether the case should be heard in open court or behind the NFL’s closed arbitration doors. But if it does move forward, and discovery begins in earnest, we could see depositions, document releases, and potentially a clearer picture of how - and why - Gruden’s emails came to light in the first place.
For now, one thing is certain: Gruden isn’t backing down. And with the stakes this high, neither is the NFL.