Barstool Sports Founder David Portnoy Uncertain About His Future

Barstool Sports founder David Portnoy may not get a new contract with the company’s owners, Penn Entertainment, when his current pact expires in 20 months.

Portnoy has been the controversial face of Barstool since he launched it as a physical newspaper in Boston back in 2003. National US casino operator Penn Entertainment began a buyout of the sports media franchise in 2020, finalizing the last of the $551 million deal this year. They have since expanded its operations into an online sportsbook open in 14 states.

Portnoy commented on his future career prospects when he appeared on podcast The Kirk Minhane Show earlier this week. “Who knows where I’ll be in 3-4 years,” he said.

Talk About It

Portnoy founded Barstool in 2003 as a short newspaper he handed out to Boston commuters. In 2007, it expanded online, and soon became a hit with young, edgy sports betting fans. 

Penn Entertainment bought the brand with the expectation it could leverage the popularity of a cool, DIY sports media group into market share for its burgeoning sportsbook. 

However the controversial side of Portnoy’s media personality has led him into conflict with Penn board members in the two years since the deal. Late last year, the New York Times labeled him a “degenerate gambler” in a headline piece. 

In a more recent example, poker player Ben Mintz was fired from Barstool’s Cracking Aces podcast earlier this month for using a racial slur. Mintz used the N-word as he was rapping along to a Bone-Thugs-N-Harmony song while live on air. 

Barstool CEO Erika Nadini fired him shortly after, reportedly at the request of Penn CEO Jay Snowden. 

Portnoy, who has been caught dropping N-bombs himself in the past, disagreed with the axing, calling it “the wrong decision.”

“He [Mintz] is just not the brightest bulb to ever come down the pipe. And he just screwed up. And he knew he screwed up. And there was no hatred behind it. No nothing,” Portnoy tweeted.

“Sold the F*ck Out“

Fast-forward a month, and Portnoy is playing coy on his future and a new Penn contract.

“There’s been some talk about (the contract)… who knows what they’re thinking at this point,” he told Minihane in their wide-ranging interview. 

When asked about accusations of selling out, Portnoy was more direct. “[We] made hundreds of millions, made millions for everybody … yeah, we sold the f*** out. And that’s what you do when you’re an entrepreneur,” he said.

Penn Entertainment operates 43 casinos and resorts across the US, as well the Barstool Sports online sportsbook in 14 legal state markets. 

As it expands, like its recent launch in Massachussets, good relationships with regulators are very important operational considerations. Therefore, controversial employees like Portnoy could prove a difficult sell.

As for his future if he does leave the company when his contract expires in 2024, Portnoy seems quite interested in pizza. He has reviewed slices online in 2017, and he suggested he could revive that in the future.

“Like a pizza show on Netflix where you’re doing like 15 minutes a spot … I like doing it,” he said. “It excites me. I think it’d be wildly successful … like the [Anthony] Bourdain of what I’m doing.”