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Dave Portnoy is back as the sole chieftain of Barstool Sports. Penn Entertainment, which bought 36 percent of the company in 2020 and increased its stake to 100 percent in February 2023, sold the company back to its founder Tuesday, “in exchange for certain non-competes and other restrictive covenants.” In other words: Penn basically gave the company back to Portnoy for free. Rarely does buyer’s remorse work out so well.
Founded in Boston in 2003 as a print publication dedicated to fantasy sports and gambling, and initially completely produced by Portnoy, Barstool Sports quickly became a juggernaut in the sports and culture landscape. Mirroring Portnoy’s irreverent approach to basically everything in life, it spawned legions of fans, known as Stoolies, and became a hot property — hence its attractiveness to investors. Alas, blending that property with Penn’s gambling operations put it on the wrong side of regulations at basically every turn. And the corporate culture installed by Penn was also anathema to Barstool’s ethos.
Portnoy’s first action when he regained ownership, for example, was to re-hire blogger Mintzy, fired in May 2023 for (apparently inadvertently) voicing a racial epithet while reading the lyrics to a rap song, a transgression for which he immediately and profusely apologized. His second was to remove cards giving employees the ability to “anonymously narc” on one another. His next move, at least publicly, was to write a blog post titled “How Fucking Brain Dead Are All My Employees?” when he looked around the office and realized no one was there.
Presumably, he fired the human resources team in between getting rid of the complaint box and referring to the majority of his team as “the dumbest group of morons who have ever lived.” If he didn’t, then Barstool must have best HR team on the planet, because that is how bosses should be allowed to behave.
Sure, people will get upset about Portnoy’s coarseness. People will also likely get upset at the return of Barstool’s overall coarseness, but the company didn’t grow and thrive despite its raucousness, but because of it. Being outrageous is part of its brand. And brands like that can’t have normal CEOs; they need a CEO who gets banned from attending NFL games and ejected from the Super Bowl after attempting to attend while in disguise.
Penn Entertainment, on the other hand, is trying to run a more traditional business, albeit one that focuses on gambling. This is where the regulatory friction came in. Having Barstool employees encourage people to make certain bets, for example, is not exactly copacetic when you’re also the bookie. This is why Penn is taking its operations to ESPN, a media company whose employees are a tad less bombastic (unless we’re talking about Stephen A. Smith).
This is the best ending possible for Penn and Barstool’s brief marriage. Penn needs to operate in a controlled environment in order to offer its services, and Barstool needs to be chaotic to fulfill its mission to entertain fans everywhere.
For while the company’s content is not appealing to everyone, the media world, particularly the sports media world, needs irreverent people like Portnoy and his idiot employees. We need people who will speak their minds without fear of getting an anonymous complaint or a visit from HR. We benefit when there are places where truly creative people can spread their wings and drink Jeppson’s Malort on video.
This is why there was no choice but for Portnoy to return as the sole owner of Barstool. As he said in his announcement of the sale, Barstool is going back to the pirate ship, to manning the cannons, to plundering. The HMS Barstool can’t properly do any of those things when Phil from legal is calling the shots instead of the Dread Captain Portnoy. As such, welcome back to the helm, El Presidente.
