Jon Gruden resigned Monday as coach of the Las Vegas Raiders, stepping aside amid a burgeoning controversy over racist, homophobic and misogynistic language that he used in emails over a span of approximately seven years before he agreed to return to the NFL in 2018 as the Raiders’ coach.

Gruden met Monday with Raiders owner Mark Davis and later told staff members that he was resigning, according to a person close to the situation.

“I have resigned as Head Coach of the Las Vegas Raiders,” Gruden said in a statement. “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.”

The NFL said Friday that it condemned a 2011 email by Gruden, who worked for ESPN at the time, that used racist language to denigrate DeMaurice Smith, the executive director of the NFL Players Association. Gruden apologized for the language that he used but said he is not a racist.

The league sent the Raiders additional emails in which Gruden used homophobic and misogynistic language to describe people and events within the league and other public figures, according to a person familiar with the case. The content of those emails was first reported by the New York Times.

The additional emails sent to the Raiders spanned from 2011 to roughly 2017, according to a person with knowledge of the case. The emails were sent from Gruden to Bruce Allen, the former president of the organization now known as the Washington Football Team, and other associates that included Jim McVay, an executive involved with the Outback Bowl, and several business leaders.

Gruden used a homophobic slur to describe NFL Commissioner Roger Goodell. He derided Goodell’s player-safety efforts and used vulgar and misogynistic language to describe the commissioner and others. He also used homophobic language in contending that Goodell should not have influenced the Rams, then based in St. Louis, to select Michael Sam in the draft. The Rams chose Sam, who was seeking to become the league’s first openly gay player, in 2014.

Davis said in a statement Monday night that he had accepted Gruden’s resignation. The Raiders named Rich Bisaccia, their assistant head coach and special teams coordinator, their interim head coach. Gruden was in the fourth season of a 10-year contract worth an estimated $100 million.

The Fritz Pollard Alliance, the diversity group that works closely with the NFL, had called Sunday for the league or the Raiders to act.

“The insensitive remarks made by Jon Gruden about DeMaurice Smith are indicative of the racism that exist[s] on many levels of professional sports,” Rod Graves, the group’s executive director, said in a statement. “Furthermore, it reveals that the journey for African Americans and other minorities in sports, is riddled with irrepressible mindsets at the highest level. It is our hope that the league and team ownership will address this matter with a remedy commensurate with these painful words. This is yet another inflection point in a society fraught with cynical social blinders, absent of respect for the intellectual capacity and leadership of minorities. When will it end?”

Speaking to reporters following the Raiders’ 20-9 loss to the Chicago Bears on Sunday in Las Vegas, Gruden was asked what he expected to happen.

“I’m not going to answer all these questions today,” he 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. And again, I apologize to De Smith and anybody out there that I have offended.”

Gruden said Sunday that the language that he used in his 2011 email was not reflective of his views on race.

“All I can say is I’m not a racist,” he said. “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. I had no racial intentions with those remarks at all. ... I’m not like that at all. But I apologize. I don’t want to keep addressing it.”

The NFL said Friday that it condemned the language used by Gruden in the 2011 email about Smith. The league declined to comment then on the possibility of taking disciplinary action.

“The email from Jon Gruden denigrating DeMaurice Smith is appalling, abhorrent and wholly contrary to the NFL’s values,” league spokesman Brian McCarthy said then in a statement. “We condemn the statement and regret any harm that its publication may inflict on Mr. Smith or anyone else.”

According to the Wall Street Journal, which first reported the 2011 email, Gruden wrote to Allen, “Dumboriss Smith has lips the size of michellin tires.” Smith, who is Black, has been the NFLPA’s executive director since 2009. He was reelected Friday to what he said will be his final term.

According to McCarthy, the NFL came across Gruden’s email to Allen as part of the investigation into workplace misconduct involving the Washington Football Team. The league “was informed of the existence of emails that raised issues beyond the scope of that investigation,” McCarthy said in his statement Friday.

Senior NFL executives reviewed the content of more than 650,000 emails, including Gruden’s to Allen, in recent months, according to McCarthy. Those executives presented a summary of that review last week to Goodell and were “sharing with Raiders executives emails pertaining to Coach Gruden,” McCarthy said Friday.