On Oct. 11, Jon Gruden, the head coach of the Las Vegas Raiders football team, stepped down from his position hours after The New York Times released emails containing racist, homophobic and misogynistic comments from him. His departure from the team was a shocking one given the amount of time he has spent working with the National Football League. Gruden has coached a Super Bowl winning team, been an analyst on ESPN, and then returned to coaching in 2018.

Gruden announced his resignation on Twitter in a statement issued by the team saying, “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’s resignation was propelled by an investigation from NFL officials on workplace misconduct. The investigation did not directly involve Gruden, but it was found that he casually and frequently used misogynistic and homophobic language across several years to talk down on and mock people involved in the NFL. He criticized the rise of women as referees, the drafting of a gay player and players protesting during the national anthem.

The emails were sent between Gruden and former president of the Washington Football Team, Bruce Allen, along with a couple of other people during his time working for ESPN. In the emails, Gruden referred to the commissioner of the NFL, Roger Goodell, as a “f—-t” and “anti football p—y” and said that the Rams should not have been pressured to draft “queers” referring to Michael Sam, a gay player drafter in 2014. There are numerous examples of him using homophobic and misogynistic language in email, including calling former President Barack Obama a “nervous, clueless p—y.” Gruden’s misconduct was not only limited to using inappropriate language when speaking about people involved with the NFL. Emails were also found between Gruden and multiple other men of women only wearing bikini bottoms, with one of the photos being of two Washington Football Team cheerleaders.

The release of Gruden and other’s emails does not look good on the National Football League that has publicly denounced racism and sexism and promised to be more inclusive to African American players, which make up around 70% of the NFL’s roster. The NFL has been criticized in the past for their lack of punishment to league personnel who have committed acts of domestic violence and other forms of harassment of women, including team cheerleaders. According to The New York Times, these emails “provide an unvarnished look into the clubby culture of one N.F.L. circle of peers, where white male decision makers felt comfortable sharing pornographic images, deriding the league policies, and jocularly sharing homophobic language.”

As for the Las Vegas Raiders, special teams coordinator and assistant head coach Rich Bisaccia will be taking over as the interim head of coach of the team.