The crowd Portnoy draws “can be all over the map,” he said. The “people-hate-my-guts crowd. A couple of them may show up, so you never know.”
Badan wondered what the over/under on protesters might be.
Alas, there were no obvious objectors to be seen. The audience at the 92nd Street Y had an air of conspicuous consumption—a Gucci bag here, a Louis Vuitton there—cut with a mix of polyester golf polos and fraternity-appropriate streetwear. Most of all, there was Barstool merch: Stu Feiner, a sports handicapper, wore a T-shirt with his own face alongside Portnoy’s, and led a brief chant for the arrival of his fellow Barstool personality Frank “The Tank” Fleming, a diehard New York Mets fan known for his viral meltdowns and weight-loss journey. (“Some could even argue that Barstool’s natural gravitational pull for weirdos has been our secret sauce throughout the years,” Portnoy writes in Cancel Me If You Can. “We’re the best there is at finding people who have no business existing in real life anywhere but with us.”)
Over his two-decade run in media, Portnoy has functioned as a reality show unto himself, buttressing his company’s flood of content and events with his own unflagging online narration of his life. To describe his following as parasocial might sell it short. His boasts on Monday (“I ran Steve Cohen off Twitter”) were met with hearty applause, never more so than when he said he wrote his book because he wanted to see it at airports, “not that I go to public airports anymore.”
The other biggest cheers of the evening arrived when Portnoy teased some political aspirations, primarily by way of bashing Zohran Mamdani and the victorious democratic socialist candidates whom the mayor backed in last week’s congressional primary. “I can’t wrap my brain around it,” Portnoy said, “and I don’t know if it’s scary or I should be scared, or, like, I got to get in politics.”
“Unlike Mamdani who’s never had a job,” he added, “I’ve had a real job and I’ve actually done a lot of good when I wasn’t doing it to run for office,” citing Barstool’s COVID-era fund for small businesses and the attention that Portnoy’s popular YouTube reviews have brought to local pizzerias.
Portnoy made similar comments in an interview with Fox News’s Jesse Watters on Monday. Rumblings about Portnoy’s potential political future have sometimes circulated in recent years alongside the concept of “Barstool conservatism”—roughly, a male-centric, Trump-era cultural libertarianism fused with anti-wokeness. Maine Senate candidate Graham Platner’s team reached out to Portnoy in May in an effort to attract the Barstool audience, only for Portnoy to promptly publish the communications on social media and repeatedly describe Platner as a “Nazi.”
After Portnoy and Badan’s discussion finished and the audience streamed out into the Manhattan night, I canvassed some of the attendees for their opinions on Portnoy’s prospects. Two young men who live in the neighborhood and work in tech and accounting thought he could pull off a political career—if he actually wanted to. “He’s got opinions, he’s got thoughts, he’s got money,” Andrew said, declining to provide his last name. “So he knows what he’s talking about most of the time or tries to.”