Jon Gruden has resigned as Las Vegas Raiders head coach following reports that he used racist, homophobic and misogynistic language in emails, as NFL Network reports. The news comes following damning reports from The Wall Street Journal on Friday and the New York Times on Monday.

“I have resigned as Head Coach of the Las Vegas Raiders. I love the Raiders and do not want to be a distraction,” Gruden, who was five games into the fourth season of a 10-year contract with the Raiders, said in a statement. “Thank you to all the players, coaches, staff, and fans of Raider Nation. I’m sorry, I never meant to hurt anyone.”

“I have accepted Jon Gruden’s resignation as Head Coach of the Las Vegas Raiders,” Raiders owner Mark Davis said.

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On Friday, The Wall Street Journal first reported that the coach used a racial trope in an email from 2011 describing executive director of the NFL Players Association DeMaurice Smith, who is Black, to Bruce Allen, then-president of the franchise now called the Washington Football Team, which allegedly stated: “Dumboriss Smith has lips the size of michellin tires.” Gruden, who was a broadcaster for ESPN at that time, claimed he did not recall penning the email, but apologized for the language. He added that he was upset about the lockout that threatened the upcoming season and “I used a horrible way of explaining it.”

Over the past several months, the league has been reviewing emails, more than 650,000 in all, in connection to its investigation into workplace misconduct in connection to the Washington Football Team. This particular email along with others was shared with commissioner Roger Goodell. “The email from Jon Gruden denigrating DeMaurice Smith is appalling, abhorrent and wholly contrary to the NFL’s values,” the NFL said in a statement. “We condemn the statement and regret any harm that its publication may inflict on Mr. Smith or anyone else.”

On Monday, the New York Times detailed emails from Gruden, which showed a pattern of Gruden using misogynistic and homophobic language, which were sent to Allen and others. In the emails, Gruden called the league’s commissioner, Roger Goodell, a “faggot” and a “clueless anti football pussy.” Goodell also denounced Jeff Fisher, then-coach of the Rams, for drafting “queers,” an apparent reference to Michael Sam, a gay player picked by the team.

Additionally, he denigrated women, sharing photos of women only in bikini bottoms, and he lambasted the employment of female referees. His ire spread to emails about President Obama during his reelection campaign and then vice-president Biden, whom he referred to as a “nervous clueless pussy.”

Gruden departs the franchise less than halfway through his contract.

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