Posting date: May 25, 20,23, 02:29h

Last updated: May 25, 2023 at 02:55h
David Portnoy, the founder of Barstool Sports and Entertainment Media Company

which he founded twenty years ago, is the face of Barstool Sport. He’s not certain for how long that status will continue.

Portnoy’s contract with Penn Entertainment (NASDAQ: PENN) is up in 20 months and there are no guarantees the two sides will reach an extension. Penn Entertainment paid $388m in February for the 64% it did not already own of Barstool Sport, which brings the acquisition price to $551m. There’s some discussion about it. Like you said

, who knows what they’re thinking at this point,” he told Minihane.[previously]That interview occurred about two weeks after Portnoy took to Twitter to tell followers he added to his already large position in Penn stock. This tweet temporarily boosted the shares. In a subsequent tweet, Portnoy asked his followers whether he should remain at Penn and show signs of overt support for the gaming company.

Portnoy/Penn Union Has Been Bumpy

Penn took its initial stake in

Barstool Sports in 2020, hoping to leverage the brash, upstart media entity to build its online sportsbook and lure a younger, hipper clientele to its regional casinos.While there are indications the deal paid dividends on the latter front, Barstool Sportsbook remains a bit player on the regulated sports wagering scene in the US. Portnoy and Penn’s marriage hasn’t always been harmonious. Barstool fired Ben “Mintzy”, a poker player, for using a racist epithet on air while reciting an rap song, on Penn’s orders, earlier this month. Portnoy has also faced allegations of sexual assault, but he has never been charged in a criminal court. Some analysts believe that Penn may sell or spin-off

, and the pool of buyers will be bigger if Portnoy is not involved. Conversely, there are analysts covering Penn who don’t’ view Portnoy as problematic.Portnoy’s Post-Barstool OptionsShould he ultimately leave

Barstool Sports and Penn, Portnoy has plenty of options. In the interview with Minihane, he toyed with the idea of a podcast or spending some time out of the limelight.He also mentioned the possibility of producing longer-form content, perhaps leveraging his famous pizza tastings into Anthony Bourdain-esque content.

“Like a pizza show on

Netflix where you’re doing like 15 minutes a spot … I like doing it. It excites. Portnoy said to Minihane, “I think it would be wildly popular… like of what I am doing.”