Jon Gruden resigned has from resigned as head coach of the Las Vegas Raiders' after racist, sexist, and homophobic emails surfaced over the weekend, CBS Sports reports. 

On Monday, Gruden informed his staff that he was resigning from his position after years of emails in which he repeatedly used derogatory language came to light

"I have resigned as Head Coach of the Las Vegas Raiders. I love the Raiders and do not want to be a distraction. Thank you to all the players, coaches, staff, and fans of Raider Nation. I'm sorry, I never meant to hurt anyone,'' Gruden said in a statement released Monday night.

Mark Davis, the owner of the Raiders, said in a statement that he had accepted the resignation.

Over the weekend, it was reported that Gruden made racist comments about DeMaurice Smith, the executive director of the NFLPA.

Gruden questioned Smith’s intelligence and wrote in the email, “Dumboriss Smith has lips the size of Michelin tires.” 

At a press conference, Gruden said he didn’t recall the email and said he was angry because of the player’s lockout.

“I probably looked at De as the villain,” he told The Athletic on Friday. “And I was really upset that there was going to be a lockout.” “I went too far calling him the Michelin lips. I never had a blade of racism in me” and that he “used a terrible way to insult a guy," he added.

Smith released a statement about Gruden’s remarks, reported.

"The email from Jon Gruden—and some of the reaction to it—confirms that the fight against racism, racist tropes, and intolerance is not over. This is not about an email as much as it is about a pervasive belief by some that people who look like me can be treated as less," Smith's statement read. "The email has also revealed why the comments by some with powerful platforms to explain this away are insidious and hypocritical. It is as if there is a need to protect football above the values of equality, inclusion, and respect.”

"I appreciate that he reached out to me [and] I told him that we will connect soon, but make no mistake, the news is not about what is said in our private conversation, but what else is said by people who never thought they would be exposed and how they are going to be held to account,” he continued.

In another bombshell, another batch of emails was discovered that Gruden sent to Bruce Allen, former president of the Washington Football Team, and others, that were routinely misogynistic and homophobic, the New York Times reports. The email exchanges were dated from 2010 through 2018 while he was employed at ESPN as a color analyst during Monday Night Football.

In the emails, he called NFL commissioner Roger Goodell a “f—t” and a “clueless anti-football p***y.” On several occasions, he used homophobic slurs to describe coaches, reporters who covered the league as well as NFL owners. Also, he made disparaging remarks toward women referees and players protesting during the playing of the national anthem. He said that Goodell should not have pressured Jeff Fisher, who was coaching the Rams at the time, to draft “queers,” a reference to Michael Sam, a gay player who the team selected in 2014.

Interestingly, since 2020, Gruden has coached Carl Nassib, a Raiders defensive end who this year became the first active player in league history to announce that he is gay.

Gruden criticized President Obama during his re-election campaign in 2012, as well as then-Vice President Joseph R. Biden, whom he called a “nervous clueless p***y.”

Back in 2018, Gruden was critical of Goodell and the league for trying to reduce concussions and said that Eric Reid, who protested during the playing of the national anthem, should be fired.

Davis described Gruden’s email exchange as “disturbing and not what the Raiders stand for.”

After Gruden’s resignation, Rich Bisaccia, the Raiders’ special teams coordinator, was named interim head coach.