Barstool Sports founder Dave Portnoy is incredibly savvy when it comes to business. Well, he turned Barstool into a media empire worth hundreds of millions of dollars by no fluke.
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In two separate transactions (2020 and 2023), Portnoy sold the company to PENN Gaming for $551 million. That cash allowed him to make the largest housing purchase in Massachusetts history. That is now part of his lavish real estate portfolio.
Portnoy’s acumen is such that he could probably have afforded to buy the properties in his portfolio without selling Barstool to PENN. And then came his masterstroke. A subsequent transaction between PENN and Portnoy functioned as a springboard for his affluent lifestyle.
In August 2023 — months after PENN finalized the full acquisition of Barstool — Portnoy bought the media company back. The price he paid? One dollar.
No, that’s not a misprint. Portnoy forked just one measly dollar bill to PENN to reacquire his “baby”. He recounted how on Shannon Sharpe’s Club Shay Shay podcast.
The reason is two-pronged — partly due to Portnoy’s actions and PENN adapting its business interests.
“[Barstool Sports] was sold to [PENN Gaming]. Gambling is super regulated. You need licenses… I’m a controversial guy, It was definitely creating issues for PENN getting licenses,” said Portnoy.
“They had an opportunity to do this deal with ESPN. [PENN was] like, ‘we’re not the right holder for Barstool…’ [and] you can’t give it to somebody, it has to be an official sale,” he added.
Portnoy admitted he benefited from “a bunch of factors all coming together for me [at the] right time.”
It was a good deal for PENN, too, since they can use Barstool’s database to engage with their loyal customers.
The sale to PENN was the second instance when Portnoy offloaded his company (the other was to Chernin Media in 2016). But now that he has full control of Barstool again, he has no intention of parting with it. If he did, PENN certainly wouldn’t mind, though.
“If I sell [Barstool] again, PENN gets 50% of the proceeds. So that, right off the bat, probably prevents it. And we’re doing great… I like where we’re at. Now, if you want to write me a check for a billion [dollars]… never say never. I reserve the right to change my mind,” Portnoy added.
Barstool is home to some of the sports industry’s most popular podcasts. Pardon My Take (No. 2) and Spittin’ Chiclets (No. 7) – both under Barstool’s wing — are among Spotify’s top 10 sports podcasts. For comparison, Club Shay Shay ranks 16th on the Spotify chart.
Unless someone tosses a billion dollars Portnoy’s way, it’s safe to say he’ll remain at Barstool’s helm for the foreseeable future.
