Las Vegas Raiders head coach Jon Gruden is resigning Monday following the revelation of homophobic and racist emails he sent to friends around the NFL.

The most recent messages, which include anti-gay and misogynistic remarks, were unearthed by the New York Times.

The emails were discovered as part of the NFL’s investigation into the Washington Football Team. In one of them, Gruden calls NFL commissioner Roger Goodell a “faggot” and “clueless anti-football pussy.” He also denounced Goodell for supposedly pressuring the Rams to pick Michael Sam in the 2014 NFL Draft, referring to the defensive lineman as a “queer.”

The messages were sent from 2011-18. Gruden told ESPN he insulted Goodell out of frustration regarding his role in the 2011 NFL lockout. .

In addition, Gruden sent an email to Allen in 2015 asking him to tell Bryan Glazer, whose family owns the Tampa Bay Buccaneers, to perform oral sex on him. Gruden coached the Buccaneers from 2002-08, winning a Super Bowl in his first season.

He also mocked Caitlyn Jenner for transitioning after she received an ESPY award.

Gruden released a statement Monday night: “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.”

Last week, it was discovered that Gruden used a racial trope to describe NFLPA head DeMaurice Smith. The messages in question were sent to former Washington team president Bruce Allen and others.

“All I can say is that I’m not a racist,” Gruden said Sunday, per NFL Media. “I can’t tell you how sick I am. I apologize again to De Smith, but I feel good about who I am and what I’ve done my entire life. I apologize for the insensitive remarks.”

Earlier, Gruden said he didn’t have a “blade of racism” in him.

The longtime head coach may say the same about his gross homophobic insults, but it will be a hard sell. The situation is magnified, because Gruden coached Carl Nassib, the first active player to come out as gay in NFL history.

Goodell’s younger brother is also gay, and as a kid, he used to protect him from bullies.

The NFL has made tremendous strides in terms of LGBTQ inclusively over the last several years, including the promotion of a video for National Coming Out Day and turning its iconic shield rainbow for Pride Month.

Outsports has asked the NFL for comment.

When Nassib came out, Gruden publicly offered his support. “I learned a long time ago what makes a man different is what makes him great,” he said.

While Gruden may believe that, his disgusting language in these emails certainly doesn’t reflect it. The coach has a lot of explaining to do.