Jon Gruden’s $150M Lawsuit Against the NFL Rolls On - And the Witness List is a Who’s Who of NFL Power Players
Jon Gruden hasn’t coached a down since 2021, but he’s still very much in the game - just not the one that’s played on Sundays. The former Raiders head coach is deep into a legal battle with the NFL, and according to new filings, he’s seeking more than $150 million in damages stemming from his abrupt exit from the league.
That number comes straight from a recently filed Case Conference Report, which outlines a laundry list of damages Gruden says he’s suffered: the loss of his job, interference with future coaching opportunities, the collapse of sponsorship deals, reputational damage, and mounting legal fees. In other words, Gruden’s not just claiming he lost a job - he’s arguing that the NFL blew up his entire career.
To rewind a bit: Gruden resigned from the Raiders in 2021 after emails he sent - containing offensive language and slurs - were made public during the league’s investigation into workplace misconduct involving the Washington Commanders and their former owner, Daniel Snyder. Gruden’s position has long been that those emails were selectively leaked to force him out, and he’s been fighting ever since to hold the league accountable.
The legal back-and-forth has been extensive, and the latest filing adds some real intrigue. Gruden’s legal team included a witness list that reads like an NFL ownership summit: Raiders owner Mark Davis, Cowboys owner Jerry Jones, Patriots owner Robert Kraft - all listed as potential witnesses. That’s not just headline-grabbing; it’s a signal that Gruden’s team is willing to pull some of the league’s most powerful figures into the spotlight.
And it doesn’t stop there. The list also includes Desiree Perez of Roc Nation, former NFLPA executive director DeMaurice Smith, and former NFL general counsel Jeff Pash. These are names with deep ties to the league’s inner workings, and their involvement would raise the stakes considerably.
Gruden filed the lawsuit just weeks after stepping down, and the legal proceedings have dragged on ever since. At the heart of it is a battle of leverage.
Gruden’s camp is pushing for a settlement, hoping the pressure from public filings and potential depositions will force the league’s hand. The NFL, meanwhile, seems content to play the long game - betting that time and public fatigue will eventually push the whole thing out of the spotlight.
But with figures like Jones, Kraft, and Davis potentially being dragged into testimony, this case isn’t going away quietly. The league may be trying to wait Gruden out, but he’s clearly not folding his hand anytime soon.
As it stands, the only clear winners in this legal saga are the attorneys - with the meter running and the billable hours stacking up. But if this case ever does make it to court, the fallout could be far more than financial. It could peel back the curtain on how the NFL handles internal investigations, leaks, and the power dynamics at the top of the sport.
For now, the lawsuit continues, the stakes remain sky-high, and the NFL’s most exclusive club might just get called to the witness stand.