Who is Dave Portnoy? Barstool Sports’ ‘El Presidente’ made millions by selling his media empire to an online casino…now, having reacquired the site, he’s ‘back to the pirate ship’ without any restraints from corporate overlords

Dave Portnoy is once again the owner of Barstool Sports, the website he founded 20 years ago and grew into a huge sports media company before selling the company to online casino operator Penn Entertainment for $551 million.

As the 46-year-old revealed in a video earlier this week, Penn is divesting from Barstool, which it used to brand online sportsbooks, and is now partnering with ESPN in a $2 billion deal. The Barstool Sportsbook app will be rebranded as ESPN as part of Penn’s 10-year agreement with the Disney cable giant.

On the surface, Penn’s decision looks like a big win for Barstool’s El Presidente. He gets his business back and doesn’t have to pay for the privilege. Plus, he’s already reversing some of Penn’s most unpopular decisions, like fired blogger and podcast host Ben Mintz (aka Mintzy), who was fired for saying the N-word while reading rap lyrics on air. Mintzy is now returning to the company, Portnoy has revealed.

But the deal comes with some conditions. The sale of all of Barstool’s shares to Portnoy came “in exchange for certain non-compete and other restrictive covenants,” which is important for a website that has historically relied on gambling-related advertising. Plus, if Portnoy ever tries to sell Barstool again, Penn will be entitled to half of the gross proceeds.

While he’s usually quick to declare himself the winner in any situation, he might be a little humbled by his experience with Penn. After years of mocking the traditional sports media with his successful genre of childish, sexualized content, Portnoy is now rebuilding his “pirate ship,” as he calls it. The following is a look back at Portnoy’s career and a look ahead at the challenges Barstool Sports will face.

Born in Swampscott on the north coast of Massachusetts, Portnoy was a high school classmate of future ESPN football analyst Todd McShay (the two actually share a birthday). The devoted Patriots fan enrolled at the University of Michigan and studied in Ann Arbor during future New England legend Tom Brady’s playing days with the Wolverines.

Portnoy returned to the Boston area after graduating with a degree in education, working for a few years for an IT market research firm before launching a four-page sports newspaper in 2003.

That paper was the first iteration of Barstool Sports and, like its successor website, lured teenage boys and young men with photos of bikini-clad women and frequent attacks on political correctness.

It was hardly an instant success, and Portnoy filed for bankruptcy protection in 2004 when he faced about $90,000 in debt and back taxes, including $30,000 in gambling losses, The New York Times reported in 2022.

But things started to change after Barstool turned into a blog in 2007. Soon the website was monetizing daily features like “Local Smokeshow of the Day,” which features photos of attractive women, one-bite pizza reviews, and “Guess That Ass,” which is more or less what it sounds like.

Meanwhile, Portnoy cultivated his “El Presidente” identity by unashamedly weighing in on controversy and fueling his own identity.

Like Mintz, Portnoy also said the N-word on-air, for which he later apologized, and was banned from Boston’s sports radio station WEEI after posting a naked photo of Brady’s 20-month-old son.

“We don’t shy away from controversy — we fan the fire,” Portnoy told NBC in 2013. “People think we’re doing everything we can to create it, but we’re not. We’re not trying to get new readers by being crazy. Our readers understand what we’re doing, and I don’t think about what it will look like to the outside world. I don’t really care.’

Portnoy takes particular pleasure in attacking Commissioner Roger Goodell over the league’s “Deflategate” scandal, in which it penalized Brady for allegedly deflating footballs in violation of NFL rules. Academics have insisted that the NFL has failed to prove its case against Brady, who may have been exonerated by league records, and Portnoy never forgave Goodell for Brady’s four-game suspension.

As a result, Portnoy and three other Barstool employees staged a protest at NFL headquarters in Manhattan in 2015, handcuffing themselves in the lobby. Four years later, Portnoy was briefly arrested after creating fake press credentials to gain entry to Super Bowl LIII in Atlanta.

It was around this time that Portnoy became increasingly political. He had always been outspoken about his stock tips and betting predictions, but with the rise of Donald Trump as a viable presidential candidate, Portnoy began to gain favor with conservatives.

“I’m voting for Donald Trump,” Portnoy wrote on his blog in 2015. “I don’t care if he’s a joke. I don’t care if he’s racist. I don’t care if he’s sexist. I don’t care. I hope he stays in the race and I hope he wins. Why? Because I love that he unsettles other politicians. I like the fact that he says no one else will say it, no matter how ridiculous it is.’

In the years to come, Portnoy would become a regular on Tucker Carlson’s Fox News program, often defending himself against a growing number of scandals.

Portnoy was subject to a 2019 National Labor Relations Board investigation over Twitter posts alleging that he threatened to fire workers if they joined a union. He eventually reached an informal settlement with the board, but suffered no significant financial penalty.

Then, following his infamous decision to sell Barstool Sports to Penn in 2020, Portnoy was accused of sexual misconduct in a 2021 Business Insider revelation alleging he had violent and aggressive sexual encounters with women, some of whom he filmed their consent. Portnoy has denied the allegations, insisting the article was a hit piece.

Portnoy later sued Insider, claiming the reporting was “false and defamatory,” but the lawsuit was ultimately dismissed.

Because of the scandal, Penn Chief Executive Officer Jay Snowden felt compelled to allay shareholder fears during a February 2022 earnings call. Snowden told his audience that, according to Bloomberg, they should “give this time to play out.” .

“No doubt there will be more to come in the coming days, just like three months ago,” Snowden said, as quoted by Bloomberg.

Shortly afterward, a second Business Insider article was published with new allegations that he filmed himself having sexual intercourse with women who were unaware they were being recorded.

The incident foreshadowed Portnoy and Barstool’s growing troubles with Penn, who was concerned about the impact of the news on its stock price and standing with regulators.

Those fears appear to have led Penn to divest from Barstool entirely, especially after the Ohio Casino Control Commission (OCCC) fined Penn $250,000 and because of a Barstool event at the University of Toledo in December 2022. event violated two state game rules that prohibit sportsbooks from advertising sports betting to students and minors.

“Penn Entertainment and Barstool Sports have gone our separate ways,” Portnoy said in a video posted. “So that’s right, for the first time in a decade I own 100 percent of Barstool Sports.

“Every time we did something, it was one step forward, two steps back,” Portnoy continued. ‘My driver’s licenses have been refused. You name it. So the regulated industry is probably not the best place for Barstool Sports and the kind of content we create.”

Portnoy’s way forward is not entirely clear.

The divorced entrepreneur is reportedly worth more than $100 million, and is currently dating model Silvana Mojica, making him jealous of his loyal army of Stoolies.

But it won’t be easy to monetize the website under Penn’s non-competition clause, and the company’s prospects appear diminutive, as each sale would result in the online casino conglomerate getting half of the proceeds.

Portnoy doesn’t seem to worry about that though. Instead, for the first time since he began selling bits of the website to major conglomerates, he’s once again in full control of Barstool’s content, for better or for worse.

“For us, for Barstool, for the first time in ages, we don’t have to watch what we say, how we talk, what we do,” he said. “It’s back to the pirate ship.”