Jon Gruden is back in football, but at an unexpected location.

The former Las Vegas Raiders head coach and ESPN commentator has signed a deal to join Barstool Sports, the website announced on Thursday. ESPN NFL insider Adam Schefter was first to report the news in a post on X on Thursday morning. The report was shortly followed by an official announcement by Barstool, in the form of a video.

Schefter reported that Gruden’s deal will run for multiple years, though exact details on how Gruden will fit into Barstool Sports’ current slate of programming is yet to be publicly announced. Barstool CEO Dave Portnoy later said on The Unnamed Show podcast that he thinks Gruden will be an “unbelievable hire.”

Portnoy later went on to indicate that he does not know exactly how Gruden will be used within the Barstool ecosystem, but also hinted that film breakdowns and in-depth football analysis would be a large part of it. That would closely mirror the role Gruden held at his previous media job at ESPN, where he was an analyst on Monday Night Football from 2009 until 2017.

Gruden first entered the public eye as the head coach of the Raiders, then based in Oakland, from 1998-2002. He then went on to coach the Tampa Bay Buccaneers, who he led to a championship in Super Bowl XXXVII with a win over his previous team.

After moving to ESPN, Gruden returned to coaching with the Raiders, now based in Las Vegas, though his second stint was not especially successful and ended in scandal. In 2021, a league investigation into the Washington Commanders turned up emails in which Gruden made an array of homophobic and anti-trans comments, in addition to making racist comments about multiple NFL figures.

Dave Portnoy said he isn’t sure exactly how Gruden will fit in to Barstool Sports yet ( 

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Getty Images)

As a result of the release of the emails, Gruden resigned from his position as Raiders head coach that October. He was later removed from the Buccanneers’ ring of honor.

Since the likely end of his NFL coaching career, Gruden has mostly been out of the public eye outside of a few consulting gigs with various teams on either side of the Atlantic Ocean. In 2023, New Orleans Saints head coach Dennis Allen hired Gruden to help transition the team’s offense under new quarterback Derek Carr, whom Gruden had worked with in Oakland. Gruden also worked as an advisor to the Milano Seamen of the European League of Football.