August 9, 2023 3 min read


Barstool Sports Back to the Pirate Ship after Penn Sells It Back to David Portnoy

The regulated industry was not the best place for Barstool, Portnoy remarked

Dave Portnoy, the founder of the sports media giant Barstool Sports, has purchased the company back from Penn. In “ probably the biggest emergency press conference” he’s ever held on Twitter/X, Portnoy explained the deal and how it came to this.

Portnoy confirmed that, for the first time in a decade, he is back in full control of Barstool Sports. He explained that Penn, which had previously hoped to take the deal “to the moon,” had underestimated how tough it is to navigate the complex regulatory landscape.

For reference, Penn acquired a partial stake in Barstool Sports back in 2020. However, Penn, Portnoy explained, struggled to make the most out of the brand because of compliance-related issues. He cited gambling regulators, media giants and stock market fluctuations as some of the challenges for Penn and Barstool Sports.

Every time Penn and Barstool did something, Portnoy said, it was “one step forward, two steps back.” Portnoy added that the two companies got “denied licenses” because of him. Although he didn’t specify what kind of licenses and in which states, he implied that his involvement in the project was enough to draw regulators’ antagonism.

“So, the regulated industry – probably not the best place for Barstool Sports and the type of content we make,” Portnoy concluded.

Portnoy Doesn’t Plan to Re-Sell the Company

The current sale of Barstool Sports is part of a bigger 10-year deal with ESPN. Under the agreement, the two partners will create a betting brand under the name ESPN Bet. As agreed, Penn will pay $1.5 billion to use the brand name and resources and will allow ESPN to buy up to $500 million in Penn stock.

ESPN Bet will effectively replace Barstool Sportsbook, Penn’s Barstool-branded sports betting brand.

Portnoy described the deal as an “unbelievable” achievement for his former partner, Penn. He said that he doesn’t feel sour about the agreement since he has a deep respect for the Penn team. The Barstool owner wished Penn and ESPN all the best and said that he will even hold the Penn stock he owns.

In the meantime, Barstool Sports is “back to the pirate ship,” Portnoy said.

For the first time in forever, we don’t have to watch what we say, how we talk, what we do. It’s back to the pirate ship. And by the way, I am never going to sell Barstool Sports, ever. I’ll hold it ‘till I die, and when I die, I’ll give it to Dan, to Kevin, whosever’s left standing, if their kids are still alive, they’ll get it, whatever. We will pass it down.

David Portnoy, owner & founder, Barstool Sports

Portnoy said that his team will now focus on producing more content. He concluded that he will remain on board and promised that the pirate ship and its cannons will continue to plunder for the next hundred years.


Angel has a passion for all forms of writing, be it fiction or nonfiction. His curious nature gives him an ace up his sleeve when researching a new topic. Angel’s thirst for knowledge, paired with adaptability, always helps him find his way around.

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