Former Las Vegas Raiders and Tampa Bay Buccaneers head coach Jon Gruden has made an unexpected career move, stepping away from the sidelines—at least for now. Amid speculation about his possible return to coaching, the Super Bowl-winning coach announced on Thursday that he’s embarking on a new venture unrelated to football coaching.
Gruden has signed a multi-year contract with Barstool Sports, as reported by ESPN’s NFL insider Adam Schefter. The news followed Barstool Sports sharing a video of Gruden teaching employees his signature Spider-2-Y-Banana play, ending with the message, “Welcome to Barstool Jon Gruden.” Gruden himself responded to the post with a characteristic quip: “You ready to learn some football?? @barstoolsports.”
This isn’t Gruden’s first foray into media. He previously served as an analyst for ESPN’s *Monday Night Football* and contributed to NFL draft coverage. However, his coaching career took a dramatic turn in 2021 when he resigned from the Raiders after just five games. A league investigation revealed emails containing racist, misogynistic, and homophobic language directed at NFL Commissioner Roger Goodell and others.
While it’s unclear if Gruden still aspires to return to coaching, his partnership with Barstool Sports marks a fresh chapter, offering fans a chance to see more of his football expertise and personality through one of the industry’s leading media platforms.
