Four years ago, his second stint as Raiders head coach ended after the New York Times reported that he had used racist, misogynistic and homophobic slurs in emails about the NFL commissioner Roger Goodell and NFLPA head DeMaurice Smith, among others. Gruden resigned after five games.

Jon Gruden has signed a multi-year deal with Barstool Sports after resigning from the Raiders due to controversial emails. His role is yet to be detailed.