According to Dave Portnoy, the Jon Gruden-Barstool Sports partnership has been a resounding success.
While it’d be surprising if he said otherwise, the Barstool founder is quite candid when a partnership goes awry. He’s also been honest about partnerships he was glad he didn’t formulate, including one with former New England Patriots head coach Bill Belichick.
But this one with another former head coach in, Gruden, it’s a different story.
After signing the former Las Vegas Raiders head coach to a multi-year contract earlier this month, Barstool threw Gruden right into the fire. He was in the company’s Gambling Cave, alongside Portnoy and Dan Katz (Barstool Big Cat) and Eric Sollenberger (PFT Commenter), amongst others, for the Eagles Thursday Night Football matchup against the Washington Commanders.
He made his presence immediately felt while sharing some scars from Philly’s WIP sports radio.
Gruden’s joining Barstool came less than 24 hours after Boomer Esiason said there was mutual interest between Gruden and the NFL teams in his return to coaching. “He’s definitely coming back,” Esiason claimed on WFAN.
A multi-year deal probably won’t preclude Gruden from making that return, but it’s certainly an unconventional stepping stone.
And while it’s unconventional, it’s absolutely working.
Portnoy referred to Gruden as a “home run hire” while on his Unnamed Show alongside Ryan Whitney and Kirk Minihane.
“People love him. He’s all in. People come out of the woodwork, like wanting to work with him,” Portnoy explained. “People — advertisers.”
And it’s working even if Gruden doesn’t know how the internet works.
He does know how advertising works, however.
Clicked on suggested youtube video of Jon Gruden doing something just to see what it was and the sponsor read at the end was absolutely amazing. pic.twitter.com/LymwVcjYEc
— Ben Koo (@bkoo) September 19, 2024
“It’s like he’s truly obsessed with football — and that’s it,” Portnoy added. “He’s just football, football, football, football; he wants to donate back to football. But, yeah, people, they don’t forget, but before his email scandal thing, he was like top of the chain; he was the guy.”
Portnoy admitted that Barstool “got a good deal” when it came to its agreement with Gruden but that he’ll make a lot of money if they do it right.
“It’s not like we’re screwing the guy,” he said.
This will be Gruden’s most mainstream media gig since he left ESPN to coach the Raiders in 2018. Gruden resigned from the Raiders in 2021 after emails were leaked showing him making homophobic and misogynistic remarks. In the ensuing years, Gruden maintained a low profile until embarking on a media tour to promote his YouTube channel this past summer.
And with Barstool’s backing, Gruden may be on the path to a full-on redemption.
