You cannot cancel a man without shame, and so Jon Gruden refuses to yield. Four years ago, he was stunned to see his crude emails leaked, ending his second stint as the Las Vegas Raiders coach, shaving five figures off his $100 million contract and transforming him from a likable, cartoonish football madman to an outcast with a digital trail of homophobic, misogynist and racist messages. Yet here he stands, over the embarrassment and under the NFL’s skin, pestering the league in court.
You cannot root for Gruden, not after all we’ve had to process about him. Nevertheless, it’s hard to ignore the theater of Gruden, who is relentless and famous for his 3:17 a.m. wake-up call, dragging the NFL into discomfort as he sues the league in hopes of reclaiming lost millions — and perhaps humiliating a few league officials during a public trial.
His effort to go to trial received another small victory this week when the Nevada Supreme Court ruled against the NFL’s desire to settle the matter through its arbitration process. The league will appeal the ruling, and there are many twists and turns left before the actual case is heard, let alone decided. But every battle makes it clear that the NFL has encountered a tenacious adversary in Gruden. Despite his indefensible character flaws, Gruden is an irresistible foil to an institution with unlimited power and the cunning to fend off all attempts at accountability.
In a strange sense, it makes Gruden the antihero we need.
He won’t go away. He’s annoying when he campaigns to return to coaching, such as he did during his recent college visit to Georgia.
“I’d die to coach in the SEC,” he told the team. “I would love it.”
And then he’s compelling as an NFL nuisance.
Those infamous emails exposed Gruden’s raw cruelty in private. He never imagined his words would come back to ruin his career several years later, and while there’s plenty of speculation about why his emails were leaked, the public has yet to learn what truly happened.
So he’s suing out of pride. And he’s suing to hold a grudge. Saying inappropriate things to friends in confidence is a pervasive human shortcoming. But most people aren’t public figures, and the smart ones know to stay off company emails. In his mind, Gruden is merely the victim of carelessness. For nearly four years, he has sought retribution.
“I’m looking forward to having the truth come out, and I want to make sure what happened to me doesn’t happen to anyone else,” Gruden said in a statement to ESPN.
The team had a 3-1 record early in his fourth season back with the Raiders. Finally, he was building a winner. Within days of the emails surfacing from his time as the “Monday Night Football” color analyst, he was sent into exile.
“What happened wasn’t right,” Gruden told ESPN, “and I’m glad the court didn’t let the NFL cover it up.”
Well, that’s still to be determined. Gruden hasn’t won anything. And as skeptical as I am about the unchecked manner in which the NFL operates, the truth can’t be as simple as a league office-sponsored hit job. I have never known the NFL to operate in that fashion. But that might mean what actually happened is both more complicated and a greater window into how the sport functions. It’s that kind of secrecy the league doesn’t want brought into the light.
Gruden is a problem, incessant and unapologetic. His conviction may force the NFL to deal with public scrutiny and reckon with how it handles internal matters. The ultimate irony is that, as the former coach attempts to scorch the NFL earth for selfish reasons, he becomes an unlikely ally for all who have been waiting for the day when a league obsessed with control must fight on someone else’s terms.
For the NFL, blessed with a brilliant legal arsenal, the threat isn’t as much about fear of losing as it is having to wrestle in the mud for the world to see. Regardless of the verdict, a Gruden trial could damage many reputations. In particular, Commissioner Roger Goodell doesn’t want to suffer through something like that on his watch, not in the twilight of a tenure that will reach 20 years in 2026.
The NFL wants to keep all of its high-profile cases out of court and far away from discovery and depositions. It settled with Colin Kaepernick in 2019 and avoided his collusion grievance getting even uglier. It would like to keep the Brian Flores racial discrimination lawsuit from advancing through the courts, and somewhat similar to the Gruden case, the league has met resistance in forcing arbitration.
You figure that, one day, the NFL will have to do this kind of fighting out of the shadows of commissioner-led arbitration, private investigations and settlements with nondisclosure agreements. But it takes a lot of money and limitless nerve to outlast the machine. Gruden is crazy enough to persist.
He’s 61 now. He works for Barstool Sports, free to be politically incorrect if he wishes. He loves the game, even though he doesn’t get to call the shots anymore. He’s not asking for permission to be in football. You can consider him banished, but he’s right outside the gate, yelling plays for all to hear.
He looks comfortable doing it, too. Unhinged is a part of Gruden’s brand. When he was beloved, he was still “Chucky.” Now that he’s shunned, he is far more dangerous than child’s play. It’s hard to suppress a competitor with nothing to lose. Gruden will exhaust all legal tactics until he forces the league to confront some uneasy questions.
The coach who did wrong also feels wronged. Gruden presents a fascinating duality. He’s not exactly repentant. He’ll never be redeemed. But against an opponent that lacks humility, his stubborn and brazen approach holds merit. It’s almost commendable, until you remember what he did.
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