Something that Jon Gruden had been trying to get for years is now no longer as important to him.

“I’m not fighting to go just to coach anywhere; I don’t want to go work in any city, I just don’t want to,” Jon Gruden said on Scripps Sports Network. “I got a nice life here, I got a hell of a team, Barstool Sports is undefeated, man, you know, it would take a hell of an opportunity for me to come back, I don’t need to do it.

“I’m still getting plenty of my itches scratched or scratches itched, whatever you say, with coaching, I have a lot of projects I’m doing, players coming in here, so I’m tentatively thinking about what I’m going to do next.”

In November 2024, Gruden joined Barstool Sports. It lists him as “Barstool’s Head Coach” and gives him several shows where he talks about football, coaches, players, and the NFL. So, it has certainly become a safe space for him.

But even while working in media, he continued to show that he wanted to return to coaching.

“The only reason I really came here is I want to coach again,” Gruden said during a speaking engagement with the Georgia Bulldogs. “I’m being honest with you, I do not bulls–t, either. I want to coach again. I’d die to coach in the SEC. I would love it. I would f—ing love it.”

He did have a solid coaching career in the NFL. Gruden first became the Raiders’ head coach in 1998 when the team was based in Oakland. He spent four seasons with the team and finished with a 38–26 regular-season record. The Raiders made the playoffs in 2000 and 2001 and won the AFC West in both seasons.

In 2002, Gruden moved to the Tampa Bay Buccaneers, went 12–4 in his first season, and led the franchise to its first Super Bowl championship.

Gruden returned to the Raiders in 2018 after agreeing to a reported 10-year, $100 million contract. However, his second stint did not go as planned, as the Raiders went 22–31 and did not reach the playoffs.

His time with the team ultimately ended in 2021, when he resigned after offensive emails he had written years earlier became public.

The emails came to light during the NFL’s investigation into workplace misconduct involving the Washington Football Team. The league reviewed more than 650,000 emails, and some of Gruden’s messages were turned over to the Raiders.

That controversy makes his return even more difficult. CBS Sports reporter Brandon Marcello spoke with college athletic directors and coaching agents in September 2024 about whether Jon Gruden could get another coaching job. During those conversations, one unnamed administrator from an SEC school said Gruden would be “untouchable” as a coaching candidate in the conference.

And interestingly, the issue is still not resolved. Gruden’s lawsuit centers on the emails that became public in 2021. He believes the NFL got those messages during its investigation into the Washington Football Team and then leaked them to The Wall Street Journal and The New York Times.

According to Gruden, the leaks hurt his reputation and contributed to his departure from the Raiders. He is now seeking compensation for the job, future coaching opportunities, contract money, sponsorships, and other losses, with his lawyers saying the total damages are well above $150 million.

The NFL has rejected Gruden’s allegation and says it did not leak his emails. The league also argues that Gruden has not provided evidence proving that the NFL or NFL commissioner Roger Goodell was behind the leaks. The case is currently scheduled for trial on May 24, 2027.