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Some things you cannot survive forever. Stupidity is one of them.

A string of e-mails laced with racism, sexism, homophobia and transphobia proved to be the undoing of Las Vegas Raiders' head coach Jon Gruden Monday when he was forced to resign after a second trove of his insulting missives to then-Washington Football Team president Bruce Allen were made public by the New York Times.

The NFL issued a public statement of condemnation when the first e-mail came out last Friday describing NFL Players Association president DeMaurice Smith in a racially insulting manner. Gruden’s tone-deaf “apology” claiming he didn’t “have an ounce of racism in me” only made matters worse.

Considering the sexist, homophobic and transphobic nature of the additional e-mails perhaps Gruden had a point. Because of the wide ranging nature of his other insulting and prejudice-laced remarks Gruden perhaps only has room for an ounce or two of racism to go along with the rest of his prejudices.

The league turned the matter over to the Raiders last Friday hoping owner Mark Davis would remove Gruden from the sidelines. He did not, and Vegas was slapped around by the lowly Chicago Bears Sunday, losing 20-9 as Gruden battled to keep control of a team that is 70 per cent African-American and ahas the first openly gay player, linebacker Carl Nassib.

That battle ended Monday night after the Times revealed the content of those additional e-mails. Even Gruden and Davis could see they were out of options. Despite the fact that we live in a time where bald-faced lies are successfully sold to a gullible public, Gruden understood there were limits.

And he’d exceeded them.

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His resignation, even if at gun point, likely will cost him the bulk of the remaining $60 million on the 10-year contract he signed four years ago, 17 years after Davis’ father, Al, grew weary of Gruden’s handling of the Raiders and traded his head coach to the Tampa Bay Buccaneers.

Gruden came back to haunt the Raiders in 2002, leading Tampa to a 48-21 win over his former team in Super Bowl XXXVII, but his tenure in Tampa soon turned sour and he was let go, eventually landing a high-profile analysts job at ESPN until the Raiders came calling.

It was during his years at ESPN that Gruden sent the e-mails that just cost him both a fortune and his reputation. Ironically, Gruden became collateral damage in the NFL’s ongoing investigation into workplace discrimination in Washington’s organization, proving once again that anything Washington owner Daniel Snyder touches, even peripherally, turns into a messy situation.

Gruden leaves the Raiders with his pockets lined with cash, his reputation in tatters and a losing record. Gruden’s return to the Raiders led to a 22-31 record, no winning seasons and no playoff appearances. All of those failures pale in comparison, however, to his moral failure made public by his e-mail exchanges with Allen, his friend from their days together during Gruden’s first tenure with the Raiders.

For a league that has put “End Racism’ signs all over its stadiums, player helmets and public utterances, the hypocrisy of retaining Gruden was profound and so troubling that even Davis, who seems to have an odd affection for Gruden, knew he had to act.

It was a sad end for Gruden and an even sadder reminder that as far as we may think we’ve come as a nation in the fight against racism, sexism and homophobia we have a long way to go before we become what we’d like to believe we are. The truth of that was not so much revealed by the content of Jon Gruden’s hateful e-mails but in the failed content of his character. That he could say with a straight face after they were made public that he “doesn’t have an ounce of racism in me” speaks to the blindness to the depth of prejudice and racism in our society.

Jon Gruden surely believes what he said, which is what makes this moment all so troubling. Because it reveals, for a brief public instant that will be too soon forgotten, that such prejudices are buried so deep in some of us that we can’t see they are there ... even when we type them out in an e-mail