Jon Gruden joins Barstool Sports: What to know about former NFL coach's career change after emails controversy

Former Raiders and Buccaneers head coach Jon Gruden has been out of the league for a few years, but the veteran is now resurfacing.

A former ESPN commentator, Gruden is rejoining the media, but this time with a different media company. The reason Gruden isn't in the NFL is because he resigned as Raiders head coach in 2021 due to controversy surrounding emails he sent regarding NFL commissioner Roger Goodell.

Since the controversy, the former Buccaneers Super Bowl-winning coach has failed in his attempts to return to the league.

The Sporting News examines Gruden's new role and why he has been out of the league in the first place.

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Jon Gruden joins Barstool Sports

Gruden is joining Barstool Sports on a multi-year contract, effective immediately. Adam Schefter broke the news which was later confirmed by Dave Portnoy.

Let's go! @barstool_gruden https://t.co/psaRpt6opo pic.twitter.com/t0v6KLMFhN

The former NFL coach rejoins the media, as he once worked for ESPN as a "Monday Night Football" broadcaster in between head coaching stints. He will presumably be part of Barstool Sports' NFL and College Football coverage.

Why did Jon Gruden resign?

In 2021, Gruden resigned midseason as coach of the Raiders when it was revealed that he used racist, sexist, homophobic and transphobic language in emails. Gruden reportedly emailed then Washington team president Bruce Allen, calling Roger Goodell a "f—t" and a "clueless anti football p—y," along with allegedly using a racist trope against former NFLPA executive director DeMaurice Smith.

Other emails that Gruden sent included targeting Michael Sam, the first openly gay player to be drafted in the NFL, along with sexist pictures and memes. The full list of emails was uncovered as part of the NFL's investigation into Bruce Allen for workplace misconduct when Dan Snyder owned the Washington franchise.

In his first comments after resigning, Gruden said he was "in a bad frame of mind at the time (in 2011)." He also tried to explain and take responsibility for his comments by speaking with The Athletic. 

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Since then, Gruden has tried to separate himself from those emails to try and return to the NFL. In 2022, he made the case for why those emails don't represent who he is.

"I'm ashamed about what has come about in those emails and I'll make no excuses for it. It's shameful. But, I am a good person. I believe that," he said. "I go to church, I've been married for 31 years and have three great boys. I still love football. I made some mistakes, but I don't think anybody in here hasn't.

"I just ask for forgiveness and hopefully, I get another shot."

However, Gruden still sued the NFL, after the fact, alleging that the league intentionally leaked the emails to get him fired. Still, his attempts to get his case heard in the Nevada court system haven't been successful.

In the meantime, Gruden has tried to get back into the league in different ways, which includes helping the Saints in 2023 when his former quarterback, Derek Carr, first signed in New Orleans.

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Jon Gruden contract

Gruden signed a multi-year contract with Barstool Sports. The rest of the deal is currently unknown.

When he resigned from the Raiders, Gruden was in the middle of a 10-year, $100 million deal he signed with the organization before the 2018 season.