The events that led to Jon Gruden’s resignation from Raiders

Jon Gruden’s second tenure as the Raiders’ coach ended abruptly Monday night, four days after revelations of racist, misogynistic and anti-gay emails surfaced. Here is a timeline from the past four days:

Friday afternoon: Minutes after Jon Gruden concludes his news conference, the Wall Street Journal publishes an article detailing the coach’s use of a racist term in a 2011 email referencing NFL Players Association executive director DeMaurice Smith.

“Dumboriss Smith has lips the size of michellin tires,” Gruden wrote in the email reviewed by the Wall Street Journal. The imagery of large lips historically has been used to promote anti-Black and racist ideas.

“I always stress being accountable, and I will take accountability for it if it was in my email,” Gruden told the Review-Journal after the story emerged. “Rubber-lipped grew into Michelin Man,” said Gruden, referring to the famous Michelin tire company mascot. “I went too far with that, and I apologize.”

Sunday morning: An ESPN report surfaces, detailing more disparaging comments from Gruden about NFL commissioner Roger Goodell.

“I was in a bad frame of mind at the time (in 2011), and I called Roger Goodell a (expletive) in one of these emails, too,” Gruden told the network. “They were keeping players and coaches from doing what they love with a lockout.

“There also were a lot of things being reported publicly about the safety of the sport that I love. I was on a mission with high school football (in the Tampa, Florida, area) during that time, and there were a lot of parents who were scared about letting their kids play football. It just didn’t sit well with me.”

Sunday afternoon: The Raiders play their worst game of the season and lose 20-9 to the Chicago Bears at Allegiant Stadium, falling to 3-2. Gruden addressed the email during his postgame news conference.

“I am not a racist. I can’t tell you how sick I am. I apologize again to D Smith,” Gruden said. “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 all. I don’t want to keep addressing it.”

Players discussed the comments after the game.

“I don’t think (the emails) had anything to do with today,” running back Josh Jacobs said. “(Gruden) came to us and got it all out. I’ve been around this guy for three years now, and I’ve never felt a certain type of way. He never rubbed me that type of way. He said what he said at the end of the day, too. But I definitely trust him. It was 10 years ago. People grow.”

Monday afternoon: Gruden is asked what he has learned from the reaction to the email.

He offers a vague response: “I’ve learned a lot, and again I’m not going to rehash the event again. I think I feel very good about the things I have learned. I also feel really good about what I stand for, as I said yesterday, and I’ll be happy to talk about football, but I’ll just leave it at that.”

Monday evening: Another report emerges, this one from The New York Times, detailing Gruden’s use of homophobic and misogynistic language in other emails during a seven-year span that concluded in 2018. About an hour after the report emerges, Gruden tenders his resignation as Raiders coach.

“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,” he said in a statement issued through the team.

Contact reporter Sam Gordon at sgordon@reviewjournal.com. Follow @BySamGordon on Twitter.