Barstool Sports has often used its status as a black-sheep little brother to ESPN to its advantage, but the most recent confrontation between the two companies nearly led to founder Dave Portnoy’s departure.
As part of a promotional tour for his new book, Cancel Me If You Can, Portnoy shared that he nearly lost his job as a condition of ESPN’s partnership with Penn Entertainment, which owned Barstool at the time. As ESPN and Penn moved to launch ESPN Bet in 2020, Portnoy alleged that the Worldwide Leader demanded that he not be involved with the partnership.
In an appearance on Barstool’s Spittin’ Chiclets released Tuesday, Portnoy shared that he met with Penn CEO Jay Snowden, who offered to buy out his stake in Penn to satisfy ESPN’s wishes. The arrangement would have seen Barstool deployed across ESPN platforms to promote ESPN Bet and Penn.
Ultimately, the Worldwide Leader’s supposed demand set in motion a series of negotiations that led Portnoy to buy Barstool back from Penn, infamously for $1, and reassert its place as one of the most successful brands in sports media.
“ESPN would have fired 90 percent of the company,” Portnoy said. “We decided to keep it, and that was basically how the company got back.”
“Fuck this espn, they tried to fire me from my own company” -Dave Portnoy https://t.co/UHBIoogLx9 pic.twitter.com/xHUBEpYhOX
— Barstool Sports (@barstoolsports) June 30, 2026
Portnoy claimed he was forced to sign a non-disclosure agreement around the transaction, which expired earlier this year when ESPN officially moved on from Penn and ESPN Bet in favor of a partnership with DraftKings (which, ironically, also partners with Barstool). The timing was fortuitous for Portnoy, who was then able to share his version of events in the new book.
Along with the controversial week-long run of Barstool Van Talk, which Portnoy writes in the book effectively smoothed tensions between him and the star hosts of Pardon My Take, Barstool’s run-ins with ESPN seem to have, in both cases, reinforced the unity and strength of Barstool, which has long defined itself in opposition to the juggernauts in the industry.
Of course, this story is unlikely to be confirmed by ESPN, but if it is anywhere close to true, it only adds to the gigantic missed opportunity of ESPN’s initial venture into sports gambling.
About Brendon Kleen
Brendon is a Media Commentary staff writer at Awful Announcing. He has also covered basketball and sports business at Front Office Sports, SB Nation, Uproxx and more.