Jon Gruden Hire Showcases the Blurred Barstool-ESPN Lines

When ESPN canceled the Barstool Van Talk late-night show in 2017, Barstool Sports founder Dave Portnoy predicted his rebel outfit would become the “next” ESPN. Guess what? Seven years later, he looks prescient in form if not in scale. Barstool is becoming more like ESPN—while ESPN is becoming more like Barstool.

Their parallel universes collided once again Thursday when Barstool hired former ESPN Monday Night Football analyst Jon Gruden. ESPN’s Adam Schefter reported it was a multi-year deal.

Gruden was once the highest-paid talent at ESPN, eventually earning $6.5 million a year toward the end of a stint that lasted from 2009 to 2017. Meanwhile, former Barstool host Pat McAfee is now one of the biggest stars at ESPN, hosting his own eponymous weekday show and starring on College GameDay. Like Gruden before him, McAfee is now one of ESPN’s highest-paid talents, licensing his show for $17 million per year. The 37-year-old former punter appeals to the younger audience who likes Barstool. All legacy media companies are struggling to attract younger readers and viewers. That’s why McAfee can get away with antics like prompting LSU fans to shout an obscene chant live on the air.

Lest we forget, the new ESPN Bet is essentially a rebranding of Barstool’s old sports betting platform. Penn Entertainment bought Barstool for $550 million in hopes of galvanizing its users into placing bets. It then had to sell it back to Portnoy for a song when controversy around the brand made state licensing difficult. Penn then signed a 10-year, $2 billion deal to integrate its betting platform into ESPN as an official partner.

Barstool’s Pardon My Take podcast has become a popular hangout for ESPN stars past and present, ranging from Chris Berman to Booger McFarland and Skip Bayless. With John Skipper (who canceled Barstool Van Talk) and Portnoy critic Sam Ponder gone, there doesn’t seem to be as much animosity anymore between Barstool and ESPN, with Clay Travis’s Outkick serving as chief ESPN critic and adversary.

After watching Gruden’s YouTube channel, Portnoy said he reached out to the former Raiders coach. Over dinner in Orlando, the two hit it off. Negotiations went quickly.

“I think he’s going to be an unbelievable hire for us,” said Portnoy.

Why Gruden Fits at Barstool

It helps that Gruden and Barstool share an enemy in NFL commissioner Roger Goodell. Gruden sued Goodell and the NFL, alleging the league deliberately leaked anti-gay, racist, and misogynist emails to destroy his coaching career. As Mike Florio of ProFootballTalk noted, Barstool/Portnoy occupy their own rung on the NFL’s “unofficial shit list.” Who can forget NFL security dragging Portnoy (who was wearing a Bobby Valentine–esque fake mustache to disguise himself) out of the 2019 Super Bowl? 

I think Gruden still wants to coach. It’s hard to know how long he stays with Barstool. In the meantime, however, Barstool has made the biggest hire in its history. Did anybody ever think a former Monday Night Football analyst would be chopping up games with the  Barstool crew?

As Barstool star PFT Commenter tweeted: “Me, coach Jon gruden, and max will be live streaming from the PMT couch commanders vs eagles for the top of the NFC East tonight. That is a sentence that would not of made any sense at all 10 years ago.”

Couldn’t agree more.