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Jon Gruden’s Awful Emails Trumped All That Job Security

Head coach John Gruden of the Las Vegas Raiders walks on the field before a game against the Chicago Bears at Allegiant Stadium.
Ethan Miller/Getty Images

How best to approach Las Vegas Raiders coach Jon Gruden’s forced resignation on Monday night, after the exposure of his many brackish malignancies about so many people in so many instances? We could start with this—he is now the second Gruden to lose his job at the clammy, careless hands of the Washington Football Team. That’s a record.

But that is not the most compelling part of how Gruden came so quickly undone as a result of his eagerness to share his retrograde world views, in writing—for that alone, he deserves the walk into the dark woods upon which he is about to embark. But Gruden’s greater sin in the eyes of those who demanded his disappearance was the unforgivable sin of punching up in a relentlessly downward-facing industry.

Yes, Gruden had secured a 10-year, $100 million contract from an owner who was willing to do anything to hire him in hopes of righting a wrong done by the owner’s father. But having Mark Davis as Gruden’s human shield only worked so long as the measuring stick was wins and losses. Davis had invested a lot in Gruden, and as such would keep him safe from the vagaries of football stuff. This was all obviously true even before anyone knew what kind of emails Gruden was sending on his leisure time.

It doesn’t really matter that all this clumsy brass predated Gruden’s return to Oakland, let alone his relocation to Las Vegas; the emails that revealed and ruined him were sent when he was still doing the league’s business in his role as a football proselytizer for ESPN. He exchanged those screeds with the since-deposed Washington general manager Bruce Allen, who in his capacity as the team’s top decision-maker used his work email to accept and respond to Gruden’s most racist, homophobic, misogynist demon-freeing. In sharing those … let’s call them “thoughts,” Gruden became vulnerable to people far higher on the chain of command than Mark Davis, who at best is the poorest and weakest of the NFL’s 32 franchise owners and is more beholden to the whims of the league’s power brokers because of the Raiders’ recent relocation to Nevada.

What Gruden thought and what Gruden wrote was all bad enough. But what really sealed his professional fate predated the arrogance that comes from being granted unlimited use of a football franchise. Gruden’s real undoing was that he took clumsy late-middle-aged-language swings at people who could brush Davis aside if need be—people like commissioner Roger Goodell for starters. Goodell might not have the power of an actual influence broker in the league—that’s for anyone between the rank of Jerry Jones and Clark Hunt—but he is close enough to all the owners that no mere employee could so freely speak so offensively as Gruden without repercussions. There would be no Chucky-face impishness to save him this time; he’d blown up all the bridges that could allow him to escape. Even if he didn’t deserve this comeuppance for being a curdled little ball of hate, he surely deserved it for being a curdled little ball of hate who didn’t understand his actual place in the universe in which he lived and worked.

Whatever you might think of his apologies, Gruden’s surprise at all of this becoming public at least has the ring of truth. He could not have known that Allen’s command of internet etiquette was so slipshod that work emails might someday become billboards; he would not have known that Washington’s Football Team would later be investigated by the league for its serially shitty treatment of its female employees. But coaches—and ex-coaches, which is what Gruden was when he put all this idiocy in writing—are supposed to be good at keeping their thoughts to themselves. They are good at this because, well, you never know when some billionaire is going to want to slice off a piece for you.

Gruden’s opinions are odious, but they are not unique; the reason he’s unemployed and other coaches with similar opinions are not is that he exposed his flank for nothing more valuable than the fun of power-painting his recidivist bile to his buddy with no tactical benefit as the reward. He talked out of school in a school that was about to be condemned for asbestos insulation, and he embarrassed people he didn’t even know he needed to worry about embarrassing. Those people do not appreciate that sort of thing.

Again, do not misunderstand that this is simply the act of a man who didn’t understand his place in the football hierarchy. Gruden didn’t understand his place in the family of humanity. He behaved like the guy in the bar who you might have once plied with a drink to get him to shut up, but the more he talked the more you just wanted the manager to 86 him entirely. Whatever he believed, Gruden’s desire to share every rancid bit of it is what did him in. His professional cohort is every bit a group of kindred spirits, but they are more adept at keeping their demons chained and out of sight. They’ll go to work this morning, and he will not.

The brash and useless ugliness of it all does seem distinctly Gruden. The man just had to be Jon Gruden even in a situation in which being Gruden was unnecessary. Gruden made his NFL reputation defying authority—as embodied by Al Davis—until Davis in his enfeebled state tired of his insubordination, no matter how well-aimed, and traded him to the team that beat his own in the Raiders’ last Super Bowl. The resulting professional turnabout did a lot for Gruden’s brand, but it was nothing the man couldn’t undo himself through the sheer force of his dedication to his own self-absorbed bullshit. When Gruden popped off to Allen, his job was to whisper showbiz wisdom to young quarterbacks and enunciate on television. He was famous, and as such comfortable tossing a middle finger at the powerful people who take greater care to mind the optics of decency that Gruden evidently thought did not apply to him—or, at the very least, thought he was insulated against when he shared them with someone who was criminally lousy at covering his tracks.

Maybe DeMaurice Smith will forgive his racism. Maybe Carl Nassib and Michael Sam will forgive his homophobia. Maybe Sheila Ford Hamp and Virginia McCaskey and Amy Adams Strunk and Jody Allen and Kim Pegula and Dee Haslam and Gayle Benson and Sarah Thomas and Maia Chaka, the last of them the first two female NFL officials, will forgive his misogyny. Almost certainly some off-brand network executive will eventually decide that a second chance should come in the form of a contract. Forgiveness has its own personal nobility; if any or all of the offended can muster it, it will be between them, their level of human decency, and the ethereal supervisors to whom they pray.

But in this plane of existence, Jon Gruden has reduced himself to nothing, and deservedly so. He forgot not who he was but who he worked for, and just how many bosses he actually had. In the National Football League, no matter whose name is on the check, you work for the ENTIRE NATIONAL FOOTBALL LEAGUE; there are people you never see and don’t think are part of your universe, but who have the power to hold you to standards that exceed a 117-112 record, a squinty smile that attempts but usually fails to achieve charm, some pre-awareness in the target demo that executives cheerfully banked on, and a championship won a million years ago. In mob terms, Jon Gruden is an earner who just lost the power to earn, and so became not just expendable but needed dismissal. He forgot that, for all he has won and earned, he still actually owned nothing in this league. And so, in the end, he got owned by those who do.