Dave Portnoy, the pizza-rating, beef-starting, staff-abusing founder of Barstool Sports, is reportedly being courted by a parade of billionaires who want to pay for him to become the Mayor of New York City. He hasn't said yes. He hasn't said no. He does have a cold, though, so today's a no. Lucky New York.
The War Chest That Could Be
The New York Post reports that Portnoy appeared on the Business of Betting podcast Thursday and dropped a claim that would sound delusional coming from almost anyone else. "I have billionaire after billionaire willing to fund a campaign if I was going to do it," he told host Jeff Edelstein, adding that the overtures are "unsolicited" and coming from "serious people."
He went further. "If I wanted to run for mayor of New York, I could have the biggest war chest probably in the history of political war chests." That is an extraordinary sentence. That is a man who has absorbed enough ESPN SportsCenter energy over two decades that even his maybe-I'll-run-for-office musings sound like pregame trash talk.
To be clear, Portnoy has not announced a campaign. He has not filed anything. He has a cold. But the fact that anonymous wealthy people are apparently lining up to write enormous checks to put El Presidente in Gracie Mansion is, by itself, a story worth sitting with for a moment. A long, uncomfortable moment.
How We Got Here
According to the New York Post, Portnoy first floated the idea of running against Mayor Zohran Mamdani last month on Jesse Watters Primetime, because of course he did. He told Watters he'd "love to" challenge Mamdani because developments in New York City have left him "losing my mind."
Mamdani, the democratic socialist state assemblyman who won the Democratic primary and the general election to become mayor, represents the kind of political left turn that makes a certain class of wealthy New Yorker reach for their checkbooks and start asking around for candidates. The fact that the candidate they appear to have landed on is a man with a documented history of creating a workplace so toxic that dozens of his own employees publicly described it as hostile, abusive, and degrading says something about the depth of the search. Exactly what it says is not flattering to anyone involved. It is, however, extremely revealing.
Who Exactly Is Dave Portnoy, and Why You Should Be Disgusted
Let's spend a real moment on this, because it matters more than the horserace framing usually allows. Portnoy built Barstool Sports into a media empire, and along the way accumulated a record that would end most careers and should have ended his several times over. In 2021, Business Insider published a detailed investigation in which multiple women accused him of filming and distributing sexual encounters without their consent. Portnoy denied wrongdoing. He then threatened the reporter on social media before the story even ran. He also threatened a Barstool employee who cooperated with the reporting. That last part bears repeating: he went after someone who told the truth about him to a journalist.
His tenure at Barstool was a rolling highlight reel of racist content, sustained misogyny aimed at female journalists and athletes, and a workplace culture so corrosive that even by the standards of early 2010s sports media it stood out. He once published the home address of a critic. He has called for journalists to be fired for covering him. When employees at affiliated properties moved to unionize, he publicly promised to immediately terminate anyone who voted yes. The National Labor Relations Board found merit in unfair labor practice charges against him. He treated workers organizing for basic protections as a personal betrayal deserving punishment. That is not a guy who got canceled unfairly. That is a guy with a paper trail.
And underneath all of it is something simpler and worse than any individual incident: Portnoy built his entire brand on the premise that cruelty is entertainment, that accountability is for losers, and that anyone who objects is just too soft to handle him. That's not a personality quirk. That's a worldview. It's the same worldview he'd carry into City Hall if the billionaires get their way.
The Soul-Searching of a Pizza Blogger
Give Portnoy this: he's not pretending this is a straightforward call. "Depends on the day you get me. Today I have a cold and don't feel great, so today I am not running for mayor," he told Edelstein, in what may be the most honest thing any potential political candidate has said out loud since at least 2016.
He also acknowledged the obvious. The New England native, per the Post, openly wonders "who the heck" would actually want to enter the political arena, and said any decision to run would come from a sense of obligation rather than ambition. "It would be a decision because I felt like I had an obligation to do it," Portnoy said.
When Edelstein pointed out that you have to be a little crazy to run for office, Portnoy agreed he qualifies as a little crazy, but noted that mayoral-campaign crazy is "a different type of crazy." He is not wrong about that. He is, however, wrong about a lot of other things, consistently, loudly, and with consequences that have followed real people around for years. The obligation he'd be fulfilling, if he runs, is to himself and the men writing the checks. Nobody else.
What the Billionaire Money Actually Means
Here is what's actually going on underneath the Portnoy circus. New York City's moneyed class, the hedge fund managers and real estate developers and private equity guys who have watched Mamdani win and are now staring at a city government they did not want, are looking for a vehicle. Any vehicle. This is what desperation looks like when it has a private jet.
Portnoy has a massive audience, a proven ability to generate media attention from nothing, and zero filter, which is either a devastating liability or exactly what a billionaire-funded outsider campaign needs, depending on your theory of politics. He's not a credible policy thinker. He is an incredibly credible attention machine. Those two things are not the same, but in modern American political life, the gap between them has been closing for about a decade.
The money being dangled at Portnoy is not really about Portnoy. It's about what Portnoy represents to people who have the resources to fund a war chest and the desperation to throw it at a sports media personality with a cold and a paper trail that most vetting committees would reject in the first five minutes. These are people who looked at the full picture of who Dave Portnoy is and decided that was fine. That tells you everything about what they actually think of New York City and the people who live in it.
The Dingo Take
Look, we've spent the better part of ten years watching celebrities and media personalities stumble into politics and win, so the reflex to laugh this off completely is one you should probably resist. Portnoy has a genuine following, a chip on his shoulder the size of a Fenway frank, and apparently enough wealthy backers to fund a small military operation. That's not nothing. That's actually kind of alarming. But let's be very clear about who we are talking about before the campaign trail nostalgia machine gets a chance to sand down the edges.
Portnoy is a man credibly accused of distributing intimate footage without the consent of the women in it. He threatened journalists for reporting on him. He threatened employees for cooperating with those journalists. He promised to fire workers for organizing. He published a critic's home address. The NLRB found merit in charges against him. None of this is disputed. None of this is ancient history being unfairly dredged up. It is a consistent, documented pattern of behavior toward women, workers, and anyone who had the audacity to hold him accountable for anything. And the billionaires recruiting him either don't know any of this, which makes them embarrassingly incurious, or they know and don't care, which is considerably worse.
Portnoy might run. He might not. He'll probably feel better once the cold clears up and we'll get three more podcast appearances before anyone knows anything definitive. But the real story here isn't whether El Presidente tosses his hat in the ring. The real story is that the wealthiest people in the largest city in the country, people with theoretically unlimited options, looked at Dave Portnoy's full record and said yes, this is our guy. New York City deserves a real opposition to any mayor it doesn't like. What it's being offered instead is a man who has spent twenty years making clear that he views accountability as an attack, workers as a threat, and women as props. The bar isn't just on the floor. Someone buried it.
