Jon Gruden resigned as the coach of the N.F.L.’s Las Vegas Raiders this week after The New York Times reported that he had made racist, homophobic and misogynistic remarks in numerous emails in the past decade. The emails were disclosed as part of an investigation into workplace misconduct on the Washington Football Team, an inquiry that did not directly involve Gruden.

Here is more about Gruden, the emails and the reaction:

Jon Gruden’s background

Gruden, 58, started his head coaching career in 1998 with the Raiders, then based in Oakland, and he won a Super Bowl with the Tampa Bay Buccaneers in the 2002 season. He was respected in league circles because of his personality and knowledge of offensive schemes.

The Buccaneers fired Gruden and Bruce Allen, the team’s general manager, after a disappointing 2008 season. Gruden was hired in 2009 as a commentator for ESPN’s “Monday Night Football.” Allen became the general manager in Washington in 2010 and later the team’s president.

Mark Davis, who became owner of the Raiders after his father, Al, died in 2011, persuaded Gruden to return to coaching in 2018 with a 10-year, $100 million contract.

What was said in the emails?

In emails from 2011, while he was at ESPN, through early 2018, Gruden frequently unleashed racist, homophobic and misogynistic language in conversations with Allen and others. During the N.F.L. team owners’ preseason lockout of the players in 2011, Gruden, who is white, used a racial trope and insulted the intelligence of DeMaurice Smith, the executive director of the N.F.L. Players Association, who is Black. Those remarks were first reported by The Wall Street Journal.

In emails detailed by The Times, Gruden used homophobic language to characterize Roger Goodell, the N.F.L. commissioner, and when referring to Michael Sam, a gay player drafted by the St. Louis Rams in 2014. He also criticized Goodell’s efforts to reduce concussions, denounced the emergence of women as referees and said that Eric Reid, one of the first players to join the former San Francisco 49ers quarterback Colin Kaepernick in protesting racism and police brutality by kneeling during the national anthem, should be fired.

Gruden also used offensive language to describe some N.F.L. owners, coaches and journalists who cover the league. And he, Allen and other men exchanged pictures of women wearing only bikini bottoms, including one photo of two Washington team cheerleaders.

How were the emails discovered?

The correspondence — more than 650,000 emails — came to light as part of an investigation into the Washington Football Team, which fired Allen in 2019. The N.F.L. fined the club $10 million this summer after concluding a yearlong inquiry that found that the team had fostered a culture of sexual harassment, bullying and intimidation. Reports from The Washington Post and The Times detailed the misdeeds of the club, including the sexual harassment of cheerleaders.

Goodell instructed league executives to look at the emails during the past few months, including those in which Gruden made offensive remarks. Goodell received a summary of the findings this month, and the league sent the Raiders some of the emails written by Gruden.

How did the Raiders respond?

On Oct. 8, after The Journal reported on Gruden’s comments about Smith, Davis, the Raiders owner, issued a statement calling the remarks “disturbing.” Gruden apologized but was allowed to coach the Raiders’ game two days later against the Chicago Bears. Before the article’s publication, Gruden held a team meeting to pre-emptively address the situation.

Gruden resigned within hours after The Times’s report on Monday that detailed more of his emails. “I love the Raiders and do not want to be a distraction,” he said in a statement, adding, “I’m sorry, I never meant to hurt anyone.”

The Raiders named Rich Bisaccia, their special teams coach, as interim head coach. Bisaccia, 61, was also the special teams coach under Gruden during the Buccaneers’ championship season in 2002.

Davis issued a brief statement on Monday accepting Gruden’s resignation. He told ESPN on Wednesday: “I have no comment. Ask the N.F.L. They have all the answers.” Beyond that, he has not publicly discussed the resignation.

Carl Nassib, the Raiders defensive end who in June became the first active N.F.L. player to come out as gay, asked for a personal day on Wednesday and did not attend the first practice after Gruden’s departure.

What was the reaction elsewhere, and what’s next?

Gruden is unlikely to coach an N.FL. team again or be associated with the league in any formal capacity.

The Buccaneers removed Gruden from their Ring of Honor at Raymond James Stadium, and he lost his endorsement contract with the footwear and apparel company Skechers. EA Sports announced that it would remove Gruden from its “Madden NFL 22” video game. The N.F.L.P.A. and the Fritz Pollard Alliance, an organization dedicated to improving diversity in the N.F.L., also condemned Gruden’s comments.

Lisa Banks and Debra Katz, lawyers who represent 40 former employees of the Washington club, have called on the league to release more evidence related to Dan Snyder, the owner of the team. Smith, the N.F.L.P.A. executive director, told USA Today that the union would petition for all of the emails to be disclosed, something the league has said it does not plan to do.