Shortly after Barstool’s seismic growth, the investors started calling. Portnoy initially brushed them off, but that all changed in 2016 when he sold The Chernin Group a majority stake in the company while keeping 100% of the editorial control. At the time, Barstool Sports was reportedly valued at somewhere between $10 million and $15 million. “This was not my cash out moment,” Portnoy wrote in an open letter to his beloved Stoolies regarding the business deal. “This was our best shot to literally take this thing to the moon. To swing for the fences.”
Still, Dave Portnoy’s greatest money-making move to date didn’t happen until 2023. Way back in 2020, Penn Entertainment purchased a 36% stake in Barstool Sports. Then, in February 2023, the entertainment company forked over another $388 million to acquire the remainder of the company. All in all, they spent a whopping $551 million for the acquisition.
Alas, the investment didn’t exactly go as planned. In a jaw-dropping turn of events, Penn struck another deal with ESPN and sold Barstool Sports back to Portnoy for a meager $1 in August of the same year. In true fashion, Portnoy issued an “emergency press conference” video wherein he explained that Barstool and Penn just weren’t right for each other. “We got denied [gambling] licenses because of me, you name it,” Portnoy lamented. “So the regulated industry [is] probably not the best place for Barstool Sports and the type of content we make.”
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Nicki
