Jon Gruden’s quest for retribution vs. NFL looks ironclad and shows no hint of a settlement

Top takeaway from ESPN’s exposé on league, Daniel Snyder reveals Gruden is 'gunning for all of them'

The report was a lot to unpack. And there was no shortage of juice.

That was the general consensus in NFL circles Wednesday, as power brokers around the league indulged in their favorite nuggets from ESPN’s detailed look at the potential sources of leaked Jon Gruden emails that cost him his job with the Las Vegas Raiders — then reportedly rippled into Daniel Snyder’s sale of the Washington Commanders. Throughout much of the day, league sources shared screenshots or quotes from portions of the story, accompanied by emojis or gleeful retorts about a swampy mess that seems to be getting only deeper by each turn of the calendar.

Whether it was Raiders owner Mark Davis reportedly telling one of his charges “F*** the NFL. And f*** Dan Snyder,” or details about the tangled partnership between the league, Snyder, the Roc Nation entertainment company and NFL commissioner Roger Goodell, there was seemingly something for everyone. But one person in particular may have walked away from the exposé with more ammunition than anyone else.

Jon Gruden.

Oakland Raiders head coach Jon Gruden responds to a question at the NFL football team's mini-camp, Tuesday, June 12, 2018, in Alameda, Calif. Gruden coached the Raiders from 1998 through 2001before being traded to Tampa Bay. Gruden replaces Jack Del Rio who was fired at the end of last season. (AP Photo/Rich Pedroncelli)
Former NFL head coach Jon Gruden is showing no intent of settling his dispute with the league in a dispute over what led to his resignation with the Raiders in 2021. (AP Photo/Rich Pedroncelli)

The former Raiders head coach has long been venting to confidants that he believed the leaking of his personal emails — which contained racist, misogynistic and homophobic language — were part of an orchestrated “hit job” by enemies in the league office. His own agent repeated that claim in August of 2022 and Gruden’s legal team has echoed it in pending litigation against the NFL. Now he has an ESPN report that details an alleged intersection of complication for the league, tying together Goodell’s handling of Snyder and the Washington team owner’s desperate bid to survive a multitude of investigations into himself and his franchise. And in between: A business relationship with Roc Nation that might have been in the center of the storm swirling around Gruden, Snyder and Goodell.

As previously stated, it’s a lot to unpack.

But the starkest underlying theme that emerged to those closest to Gruden by late Wednesday night: It was all fuel to a fire that has burned white hot since Gruden was ousted from the Raiders.

“Jon’s going to take this all the way,” said a league source with personal ties to Gruden, Goodell and former Washington executive Bruce Allen — who was the recipient of the leaked Gruden emails. “It’s as personal as it gets.”

“This” refers to Gruden’s pending lawsuit, which is currently paused in Nevada’s legal system as the state’s Supreme Court considers the NFL’s appeal to force the complaint into the league’s private arbitration system. And “all the way” refers to where Gruden has been telling his inner circle he wants the lawsuit to go: Into a courtroom, where NFL power brokers like Goodell and Snyder would have to testify under oath about their handling of his emails.

“This isn’t about money,” the source said. “Jon doesn’t give a s*** about money. He has money. But he thinks Goodell and [NFL general counsel] Jeff Pash f***** him. He’s gunning for all of them.”

Since the emails were leaked to the Wall Street Journal and New York Times in October of 2021, many of Gruden’s closest allies privately set aside the content of what Gruden had written and focused on one overriding question: In the expansive investigation of the Commanders franchise and some 650,000 emails and communications, why were his the only ones singled out and who had the motivation to use them against him?

ESPN’s piece illuminated some of the most logical candidates from the chain of custody. But Gruden’s pound of flesh and any additional collateral damage can be achieved through only the legal system. And on the heels of this week’s revelations, it appears less likely than ever that this will be a fight resolved by a settlement.

This article contains affiliate links; if you click such a link and make a purchase, we may earn a commission.