LAS VEGAS (KLAS) — In a statement released Monday afternoon, Las Vegas Raiders head coach, Jon Gruden said he was resigning from his post. The announcement was made after new emails surfaced showing he used racist, misogynistic and homophobic comments.

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.

Jon Gruden, former head coach for the Las Vegas Raiders

The announcement was imminent after a NY Times investigation Monday revealed Gruden had not only used racist comments in an email in 2011, rather that he had regularly used derogatory language in emails during his employment with ESPN.

The report specifically noted that for several years, Gruden “casually and frequently unleashed misogynist and homophobic language … to denigrate people around the game and to mock some of the league’s momentous changes.”

The NY Times investigation notes emails Gruden sent while he was working for ESPN that show that he criticized women referees, drafting of gay players and was intolerant to players protesting during the national anthem.

The report highlights excerpts of various emails Gruden sent to Bruce Allen, the former president of the Washington Football Team, and others. One in particular, where Gruden calls the “leagues commissioner, Roger Goodell, a “faggot.”

The report further reveals the language and comments Gruden made during his time at ESPN. The full NY Times article revealed too many instances that could not go ignored by the league or the owner of the Raiders Mark Davis who also released a statement shortly after Gruden’s official resignation.

I have accepted Jon Gruden’s resignation as Head Coach of the Las Vegas Raiders.

Mike Davis, owner of the Las Vegas Raiders

Gruden’s racist comments came under fire on Friday, after the first email was made public and revealed Gruden wrote complaining about then head of the NFL’s Players Association, DeMaurice Smith, and wrote to Bruce Allen, then with the Washington Football Team that “Dumboriss Smith has lips the size of Michelin tires.”

Gruden had told the Wall Street Journal who first reported on the racist comments that he could not recall the email and added, “I was upset. I used a horrible way of explaining it. I don’t think he’s dumb. I don’t think he’s a liar. I don’t have a racial bone in my body, and I’ve proven that for 58 years.” Gruden was working for ESPN at the time and the NFL was going through collective bargaining.

Earlier on Monday, DeMaurice Smith the Executive Director of the NFL Players Association responded via Twitter about the comments made by Jon Gruden in a 2011 email.

Smith says in a tweet, in part: “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.”

He goes on to add that Gruden reached out to him since the email was first released last week.

The NFL Friday responded with a statement this afternoon saying through a spokesperson, “The email from Jon Gruden denigrating DeMaurice Smith is appalling, abhorrent and wholly contrary to the NFL’s values. We condemn the statement and regret any harm that its publication may inflict on Mr. Smith or anyone else.”