The writing was already on the wall for Jon Gruden and his $10 million per year contract with the Las Vegas Raiders. Last week, the Wall Street Journal exposed some of Gruden’s comments about NFL Players Association honcho DeMaurice Smith in which Gruden referred to him as as having, well …

The email was written in 2011 in an exchange between Gruden, who is white and was an analyst for ESPN at the time, and Bruce Allen, who was then the president of the Washington Football Team.

“Dumboriss Smith has lips the size of michellin tires,” Gruden wrote about Smith in the exchange.

The email was discovered during a review of workplace misconduct at the Washington Football Team that ended this summer.

Yikes. Gruden tried to apologize and claimed that he meant that as a term for liar rather than a racial reference, but lip-size comments seem pretty clearly tied to Smith’s ethnicity. That alone would likely have resulted in Gruden’s termination at some point, but it turns out that Gruden had plenty more to say about others too:

Jon Gruden has resigned as coach of the Las Vegas Raiders after emails he sent before being hired in 2018 contained racist, homophobic and misogynistic comments. …

It was a rapid downfall for Gruden, who is in the fourth year of a 10-year, $100 million contract he signed with the Raiders in 2018. It started on Friday when the Wall Street Journal reported that Gruden used a racist term to describe NFL union chief DeMaurice Smith in a 2011 email to former Washington executive Bruce Allen.

The emails were discovered in a workplace misconduct investigation into the Washington Football Team but ended up costing Gruden his job when they also showed Gruden denounced the drafting of a gay player and the tolerance of players protesting during the playing of the national anthem among other issues.

Gruden apologized for his “insensitive remarks” about Smith, saying they were made out of frustration over the 2011 lockout. But the latest emails sent from between 2011-18 when Gruden was an analyst for ESPN show his use of derogatory language went well beyond that.

What did Gruden say in the other e-mails? The homophobic language came in part from his description of NFL commissioner Roger Goodell, although not all of his usage had to do with sexuality. Most of it was colloquial usage that we’d remember from our own coaches:

Gruden’s messages were sent to Bruce Allen, the former president of the Washington Football Team, and others, while he was working for ESPN as a color analyst during “Monday Night Football.” In the emails, Gruden called the league’s commissioner, Roger Goodell, a “faggot” and a “clueless anti football pussy” and said that Goodell should not have pressured Jeff Fisher, then the coach of the Rams, to draft “queers,” a reference to Michael Sam, a gay player chosen by the team in 2014.

Gruden’s comments about Goodell might have used salty language, but I heard worse from my high-school coaches. He clearly was using the first term to express weakness and cowardice (as well as in “pussy”), a rather routine usage in sports. The part about actually gay players is tougher to explain away, other than Gruden is a product of his own time in that regard — and that Gruden was hardly alone in the NFL about Sam at the time. Call it “toxic masculinity,” if you will, but don’t doubt for a moment that Gruden was the rule rather than the exception from this era.

To that point, it’s clear that Gruden used this language in the non-sexual sense often and broadly. Even Joe Biden got the P-treatment:

Gruden also criticized President Obama during his re-election campaign in 2012, as well as then-Vice President Joseph R. Biden, whom Gruden called a “nervous clueless pussy.” He used similar words to describe Goodell and DeMaurice Smith, the executive director of the N.F.L. Players Association.

After Afghanistan and Biden’s abandonment of Americans there, it’s impossible to rebut the gist of Gruden’s comment, no?

Had Gruden made these statements publicly, or as part of his official communications in the NFL or at ESPN, then this outcome would be a demonstration of accountability, if somewhat harsh considering Gruden’s intent. It seems much more problematic applying this kind of punishment to private personal emails to Allen. To underscore that point, the NYT even points out that Gruden sent topless pictures of women to Allen and others, one photo of which were of two WFT cheerleaders. If those were covertly taken, then a crime was committed, but if they were public and/or taken with consent, then there’s no issue at all — or shouldn’t be, especially not in private communications. (See update below.)  So why mention it at all, except as a way to humiliate Gruden?

With that in mind, why didn’t Gruden just tough it out, offer profuse apologies, promise to do better? Isn’t that worth a try with $60 mil on the line? The New York Times notes that Gruden’s team now includes someone who might make it uncomfortable if Gruden stuck around:

Although not with a team at the time, Gruden was still influential in the league and highly coveted as a coach. He had won a Super Bowl with the Tampa Bay Buccaneers following the 2002 season. And in 2018, he was hired for his second stint as the head coach of the Raiders franchise, which includes defensive lineman Carl Nassib, the first active N.F.L. player to publicly declare that he is gay.

One has to wonder whether Nassib would have cared about that more than winning, or if the team and the league decided to white-knight for Nassib. But perhaps Gruden just decided that he’d been humiliated so much that it would be impossible to provide leadership in the locker room any longer. After all, a coach has to get his team to rally behind him and trust his judgment, both on and off the field. Gruden knows that well enough.

Will Gruden come back? After a season or two of sensitivity training and public atonement, maybe. At least by that time the league and its fans will have gained some perspective on Gruden and might better appreciate the ethically murky context of peeking into someone’s personal e-mails for dirt. Gruden owes DeMaurice Smith and perhaps Michael Sam an apology, but perhaps the league owes Gruden one, too.

Update: I had forgotten the context of the probe:

@EdMorrissey In re: your post on Gruden – went wide of the goal posts. The emails were sent from his team-provided address and subject to discovery during NFL’s investigation into alleged sexual harassment against WFT cheerleaders by mgmt. Topless photos were part of the suit.

— Njia, Presented by Rocket Science (@CallMeNjia) October 12, 2021

Fair point, and that made the pictures relevant, so my apologies to the New York Times.

One other point, too: these messages came from Gruden’s private account but apparently went to Allen’s business account with the then-Redskins. I doubt that Gruden thought they would ever get publicly trawled for politically incorrect speech, but the expectation of privacy is a bit lower in this case. Business records routinely get subpoenaed, including e-mails, which is why businesses will caution about the use of official e-mails for anything other than business. Gruden’s judgment seems exceptionally poor in multiple ways.