LAS VEGAS (KLAS) — One day after stating he wasn’t racist following a 20-9 loss to the Chicago Bears, in response to racial remarks from 2011, Las Vegas Raiders head coach Jon Gruden is expected to resign, according to sources.

First reported by NFL Network reporter Tom Pelissero, the resignation comes following the head coach’s 2011 racial remark about players’ union leader DeMaurice Smith. A Wall Street Journal story last week noted that Gruden, then working for ESPN, referred in a racist way to Smith’s facial features in an email. Gruden’s criticism over racist comments continued to escalate Monday afternoon when a New York Times report uncovered more emails that showed Gruden used misogynistic and homophobic terms in the past.

In the report released Monday afternoon, the New York Times states that in 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.”

Jon Gruden’s resignation comes three days after the Wall Street Journal reported his email about DeMaurice Smith, and hours after the New York Times reported other emails including derogatory and offensive language, among other things. A swift and stunning fall. https://t.co/zkzkVryyfe

— Tom Pelissero (@TomPelissero) October 12, 2021

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

The report highlights a particular email Gruden sent to Bruce Allen, the former president of the Washington Football Team, and others where Gruden called the “leagues commissioner, Roger Goodell, a ‘faggot.’

Gruden coaches Carl Nassib, the NFL’s first active player to come out as gay.

Gruden apologized for his “insensitive remarks” when asked about the decade-old emails following the Raiders’ 20-9 loss to the Chicago Bears.

“I’m not a racist,” Gruden said. “I can’t tell you how sick I am. I apologize again to D Smith, but I feel good about who I am and what I’ve done my entire life. … I had no racial intention with those remarks at all. I’m not like that at all. I apologize. I don’t want to keep addressing it.”

Gruden ended his news conference after a series of questions about the emails and his behavior. He said he has not been contacted by the NFL about the remark, but “we’ll see what happens here in the next few days.”

“I’m not going to answer all these questions today,” Gruden said. “I think I’ve addressed it already. I can’t remember a lot of the things that transpired 10 or 12 years ago, but I stand here in front of everybody apologizing. I know I don’t have an ounce of racism in me. I’m a guy that takes pride in leading people together, and I’ll continue to do that for the rest of my life.”

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 Associated Press contributed to this report.

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