Former NFL coach Jon Gruden has signed a multi-year deal with Barstool Sports, marking his return to media after his resignation from the Las Vegas Raiders in 2021 over leaked emails containing racist and sexist language. While his specific role at Barstool is unspecified, there is speculation that it could be a stepping stone for a return to coaching, possibly at the college level. Despite past controversies, Gruden has launched a YouTube channel and is involved in a lawsuit against the NFL, challenging the arbitration of his case. Barstool Sports, known for its contentious relationship with the NFL, seems a fitting platform for Gruden, who sees himself as an agitator within the league. Gruden has expressed a strong interest in returning to coaching and believes he can contribute positively to a team. His ongoing legal battle with the NFL and recent media ventures highlight his complex journey back into the public eye.