Dave Portnoy and Barstool Sports have been inextricable since the company’s founding, but that may or may not be the case in the long run.

In an appearance on “The Kirk Minihane Show” earlier this week, Portnoy revealed that his contract is up in 20 months and that he’s not sure if he will reach an extension with parent company Penn Entertainment.

Penn finalized its acquisition of Barstool, which began in 2020, earlier this year, paying a total of $551 million to buy it from The Chernin Group.

The topic came up when Minihane asked Portnoy how he felt about Dan Katz leaving New York to open a Barstool office in Chicago in the coming months, and bringing dozens of employees with him.

“I think it’s great … Who knows where I’ll be in 3-4 years. I think Dan, which I would say is very good for Barstool, is clearly locked in for a very long time. He’s creating this huge fantasy factory there. I think it’s great for Barstool.”

Minihane asked Portnoy if he had an end date at the company for himself in mind.

“Well, no. My contract’s done in 20 months so,” he said.

Asked if there’s been any talks, since it’s still early, Portnoy answered, “There’s been some talk about it. Like you said [previously], who knows what they’re thinking at this point.”

Portnoy founded Barstool Sports in 2003 as a free print tabloid for transit commuters in the Boston area, eventually building it into the sprawling national digital media empire that was purchased by Penn, a brick-and-mortar casino company, to develop an online sportsbook.

Earlier in the interview, when Portnoy spoke about his disagreement with Penn CEO Jay Snowden about firing host Ben Mintz for rapping a racial slur on a live stream, he expressed gratitude about the partnership considering other gambling companies were hesitant to take a chance on Barstool.

Dave Portnoy revealed that his contract to run Barstool Sports is up in 20 months and that he’s not sure if he will renew with parent company Penn Entertainment.
Zuffa LLC

Dave Portnoy and Dan Katz at UFC 281.
Dave Portnoy and Dan Katz at UFC 281.
Zuffa LLC

Nevertheless, the subtext of what Portnoy means when he says he doesn’t know what the company is thinking is that they might calculate the cost/benefit of Barstool being less of a lightning rod with state gambling regulators if the controversial Portnoy leaves when his deal is up.

Barstool Sportsbook got licensed in Massachusetts earlier this year, but it was an arduous process, and the platform is not licensed in New York.

Most states with legal sports betting have ultimately licensed Barstool Sportsbook.

Dave Portnoy and Seth Meyers eat pizza in 2017.
Dave Portnoy and Seth Meyers eat pizza in 2017.
NBCU Photo Bank/NBCUniversal via

Minihane broached the hypothetical on what Portnoy would do for work if the company told him they appreciated what he built but felt it was time to move in a new direction.

“I go back and forth on that,” he said.

He dismissed the idea of launching a whole new media business, but had a few ideas he’s dabbled with.

“Would I just do a podcast a week that’s totally unfiltered? Would I enjoy doing that? Maybe,” he said. “There’s part of me that thinks I’d be like OK I’m done.

“I go through different things, the pizza stuff, I’d like to do longform, I enjoy doing that … Like a pizza show on Netflix where you’re doing like 15 minutes a spot … I like doing it. It excites me. I think it’d be wildly successful … like [Anthony] Bourdain of what I’m doing.”