Dave Portnoy’s future at Barstool Sports is uncertain with the founder’s deal expiring in 20 months

Dave Portnoy’s future at Barstool Sports appears to be up in the air, with the digital media site’s founder considering leaving if he doesn’t reach an extension with parent company Penn Entertainment before his deal expires in 20 months.

In an appearance on “The Kirk Minihane Show” earlier this week, Portnoy was asked if he had an end date to leave the business he started nearly 20 years ago in the Boston suburb of Milton, Massachusetts.

“Well no,” said the 46-year-old. ‘So my contract ends in 20 months.’

Barstool was fully acquired by Penn earlier this year after a $551 million purchase was agreed with The Chernin Group. Penn first began the process of buying Bar Stool in 2020.

Portnoy announced the expiration date of his contract as he commented on Dan Katz’s decision to open a Barstool office in Chicago in the coming months, bringing a dozen employees from the New York office.

“I love it,” Portnoy said. Who knows where I will be in 3-4 years. I think Dan, who I would say is very good for Barstool, has obviously been locked up for a very long time. He creates a huge fantasy factory there. I think it’s great for Barstool.’

Asked if there have been talks with senior Penn executives about a new, long-term deal, Portnoy said, “There’s been some discussion. As you said [previously]who knows what they are thinking right now.’

Earlier in May, the founder of Barstool Sports claimed he had done everything he could to keep the company’s former podcast host, Ben Mintz. At the time, he added that he feared Mintz’s firing was a “death knell” for the company, as Penn’s stock price fell significantly after a large number of backlashes.

Portnoy clashed with Penn executives over several issues, including Ben Mintz’s firing in May

Portnoy said he disagreed with Penn CEO Jay Snowden over Mintz’s sudden firing

However, while appearing on ‘The Kirk Minihane Show’, Portnoy appreciated his partnership with Penn CEO Jay Snowden as other betting companies were hesitant to take a bet on Barstool.

If the University of Michigan graduate leaves the company once his deal is finalized, Barstool could become more attractive to gambling regulators through severed ties with its founder, who once made the New York Times headline for his “hit piece” on his gambling habits.

Barstool finally obtained its gambling license in Massachusetts earlier this year after a lengthy and arduous process, but the company’s sportsbook remains out of action in New York.

Portnoy, 46, doesn’t know what to expect when he finally decides to leave Barstool

Of the 38 states where online sports betting is legal, Barstool Sports can operate in half, including Pennsylvania, New Jersey, and Louisiana to name a few.

When asked about the possible scenario where Penn would tell him it’s time to move on and what the next step is, Portnoy told Minihane, “I’ll go back and forth on that.”

The outspoken sports fan from Boston brushed off claims that he would start a new media company, although he has other ideas on his mind.

“Would I just do a podcast a week that is totally unfiltered? Would I like that? Maybe,’ said Portnoy. “There’s a part of me that thinks I’d be like, ‘Okay, I’m done.'”

“I go through different things, the pizza things, I’d like to do longform, I like doing that,” he added. ‘Like a pizza show on Netflix where you spend about 15 minutes per spot. […] I like doing it. It turns me on. I think it would be hugely successful [Anthony] Bourdain of what I do.’