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 founder considering leaving if he doesn’t reach an extension with parent company Penn Entertainment before his contract expires in 20 months.

During 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 suburbs. from Boston, to Milton, Massachusetts.

“Well, no,” the 46-year-old said. “My contract is over in 20 months therefore.”

The barstool was fully acquired by Penn earlier this year after a $551 million purchase was completed with The Chernin Group. Penn began its bar stool buying process in 2020.

Portnoy revealed the expiration date of his contract while discussing Dan Katz’s decision to open a Barstool office in Chicago in the coming months and bring with him a dozen employees from the New York office.

“I think it’s great,” Portnoy said. ‘Who knows where I will be in 3-4 years. I think Dan, who I would say is very good at Barstool, has clearly been locked up for a very long time. There he created this huge factory of fantasies. I think it’s great for Barstool.

When asked if there had been any discussions with senior Penn executives about a new long-term deal, Portnoy said, “There have been discussions about it.” Like you said [previously]who knows what they are thinking at this point.

Earlier in May, the Barstool Sports founder claimed he had done everything in his power to try to restrain former company podcast host Ben Mintz, who was fired for saying a racial slur reading the lyrics to a rap song on a live stream. At the time, he added that he feared Mintz’s firing would be a “death blow” to the company, as Penn’s stock price had fallen significantly after a high volume of backlash.

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

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

However, during his appearance on “The Kirk Minihane Show”, Portnoy enjoyed his partnership with Penn CEO Jay Snowden, considering other game companies were hesitant to take a chance on Barstool.

If the University of Michigan graduate ends up leaving the company once his contract is complete, then Barstool could become more attractive to state gaming regulators due to severed ties with its founder, who tore the New York Times once for his “hit” on his gambling habits.

Barstool finally got its gambling license in Massachusetts earlier this year after a long and arduous process, but the company’s bookmaker remains inoperative in New York.

Portnoy, 46, does not know what awaits him if he finally decides to leave Barstool

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

Asked about the potential storyline of Penn telling him it’s time to move on and what to expect, Portnoy told Minihane, “I’m going back and forth on that.”

The outspoken Boston sports fan dismissed claims that he was going to start a new media company, although he has other ideas in mind.

‘Would I just do one podcast a week without any filters? Would I appreciate that? Perhaps, said Portnoy. “There’s a part of me that thinks I’ll be like, ‘Okay, I’m done.’

“I go through different things, the pizza stuff, I’d like to do long form, I like to do that,” he added. “Like a pizza show on Netflix where you do about 15 minutes per seat. […] I like doing it. It excites me. I think it would be a wild success, like [Anthony] Bourdain of what I do.