Super Bowl-winning coach Jon Gruden has made a surprising career move—but it’s not in the NFL, and it’s certainly not in any typical football setting. Instead, the 61-year-old coach, who resigned from his position as head coach of the Las Vegas Raiders in 2021, has now joined Barstool Sports, a company best known for its irreverent sports and pop culture content.
Gruden’s new role with Barstool is currently unspecified, adding even more intrigue to his unexpected decision.
According to ESPN’s Adam Schefter, Gruden signed a multi-year contract with Barstool Sports, signaling a significant shift in his professional focus. The company’s outspoken founder, Dave Portnoy, also shared a video confirming the news, which featured Gruden teaching Portnoy and other Barstool personalities a football play on a whiteboard.
The video encapsulated the kind of informal, humorous content that Barstool is known for, giving fans a glimpse of Gruden’s new dynamic.
This surprising move comes nearly three years after Gruden resigned as the Raiders’ head coach amid controversy. In 2021, Gruden stepped down following the leak of emails in which he used racist, homophobic, and misogynistic language.
The leaked emails, which dated from 2011 to 2018, were sent by Gruden while he worked as an analyst for ESPN and were addressed to former Washington Commanders president Bruce Allen. The emails were discovered as part of a larger investigation into the workplace culture of the Washington football team, involving a trove of 650,000 messages.
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Gruden’s abrupt departure from the Raiders in 2021 sparked a legal battle, as the former coach subsequently filed a lawsuit against the NFL.
He has alleged that the league leaked the emails in a deliberate attempt to force his resignation, which has added an ongoing element of tension between him and the NFL. The lawsuit remains unresolved, and Gruden has consistently argued that he was unfairly targeted.
Despite the controversy, Gruden’s legacy as a coach is undeniable. He led the Tampa Bay Buccaneers to victory in Super Bowl XXXVII, defeating his former team, the Oakland Raiders, in the process. His coaching career began with the Raiders in Oakland from 1998 to 2001, before he moved to the Buccaneers, where he coached from 2002 to 2008.
After a decade away from coaching—during which he worked as a prominent analyst on ESPN’s “Monday Night Football”—Gruden returned to the Raiders in 2018 for a second stint, this time in Las Vegas. He coached the team for 53 games before stepping down midway through the 2021 season.
Rumors of Gruden’s potential return to the NFL have circulated ever since his departure, with many speculating about whether he might find another opportunity in the league. Just this week, former NFL quarterback and current WFAN radio host Boomer Esiason expressed his belief that Gruden is determined to make a comeback. “I can confirm… that there are teams interested in him. And if it’s not this year, it’s next year. But he’s coming back, he’s definitely coming back,” Esiason said, suggesting that Gruden’s coaching days may not be behind him just yet.
For now, however, Gruden appears to be charting a different path with Barstool Sports, embracing the company’s unconventional and often boundary-pushing style. The move may provide Gruden with a platform to stay connected to the sport he loves, while also showcasing his personality outside the pressures of an NFL sideline.
It’s an unexpected twist in the career of a coach who has seen his fair share of highs and lows, and it remains to be seen what Gruden’s new venture will bring—both for him and for Barstool Sports.
Whether this move signals a permanent shift away from the NFL or simply a temporary detour until another coaching opportunity arises, one thing is clear: Jon Gruden is not done making headlines.
Fans of both Gruden and Barstool Sports will be eager to see how this partnership evolves, and whether the coach known for his fiery personality can find a new niche in the ever-changing world of sports media.
