Jon Gruden’s legal battle with the NFL and Commissioner Roger Goodell is still alive and well - and if his claims hold, the financial stakes are massive.
In a newly filed Case Conference Report dated February 5, Gruden’s legal team put a number on the damages they’re seeking: more than $150 million. That figure covers a wide range of alleged losses, including the termination of his coaching contract, lost future job opportunities, sponsorship deals that vanished, reputational harm, and the mounting legal costs tied to this long-running dispute.
This lawsuit stems from Gruden’s abrupt resignation as head coach of the Raiders back in 2021, following the public release of emails he had sent during his time as an ESPN analyst. Those messages - which contained offensive language - were uncovered during the league’s investigation into the Washington Commanders and their former owner, Daniel Snyder. Gruden has maintained from the start that the emails were selectively leaked with the intent to force him out of his job.
This latest filing comes after an “early case conference,” which the NFL declined to participate in. According to the report, the league believes the case is still on hold while it appeals a previous court decision that denied its motion to dismiss under Nevada’s anti-SLAPP statute - a law designed to quickly shut down lawsuits that could stifle free speech.
Gruden’s legal team isn’t pulling any punches. The Case Conference Report includes a hefty list of potential witnesses - some of the most powerful names in football.
Among them: Commissioner Goodell, former NFL general counsel Jeff Pash, league spokesman Brian McCarthy, Snyder, Raiders owner Mark Davis, Cowboys owner Jerry Jones, Patriots owner Robert Kraft, former NFLPA executive director DeMaurice Smith, and even entertainment executive Desiree Perez of Roc Nation. Attorneys from high-profile law firms like Paul Weiss and Reed Smith are also named.
Now, to be clear: the report doesn’t confirm that all of these individuals will be deposed. It simply lists them as potential witnesses. There’s no indication yet that Gruden’s team is actively trying to compel testimony from any of them - but the list signals just how wide a net they’re casting.
The report also identifies several NFL teams with potentially relevant information: the Commanders, Raiders, Cowboys, Patriots, Seahawks, Giants, Jets, and Dolphins. Notably, it doesn’t mention any of the reporters involved in publishing the original email stories.
One of the more eye-catching elements of the filing is a request for documents Gruden’s team believes the NFL should turn over immediately. That includes the entire trove of 650,000 documents gathered during attorney Beth Wilkinson’s investigation into the Commanders, as well as something referred to as the “Blackmail PowerPoint.” According to the report, that presentation - allegedly created by Snyder and/or the Reed Smith law firm - contains communications involving Goodell and Pash.
As of now, no settlement talks have taken place, and it’s unclear whether the NFL will try to take the case to the U.S. Supreme Court in an effort to enforce arbitration - a process that would be overseen by the league itself.
This case has been grinding along for more than four years, largely bogged down by procedural fights over whether it should be handled in open court or behind closed doors. But unless it’s dismissed or settled, the next phase could finally bring depositions, document disclosures, and a deeper look behind the curtain of one of the NFL’s most controversial off-field sagas in recent memory.