Barstool Sports founder Dave Portnoy has threatened to move the company’s headquarters out of New York City if Democratic socialist Zohran Mamdani claims victory in the mayoral election on Nov. 4.
Portnoy, 48, who has an estimated net worth of around $250 million, founded Barstool Sports in 2003 in his home state of Massachusetts; however, the company has been headquartered in New York City for several years now.
But the entrepreneur and podcast host has now admitted that he’s started eyeing up other potential locations for his business—which was valued at around $600 million in 2023—although he admitted that he would hate to make a change that would negatively impact his employees.
“If it was just me, I would move the company out of New York City because I hate this guy so much,” Portnoy said during livestream an appearance on Barstool’s “The Unnamed Show” podcast.
“But I won’t because there’s a lot of people in New York, and I don’t want to change their lifestyle for it.”
It is not the first time that Portnoy has hinted at plans to flee the Big Apple—revealing in a recent livestream that he had considered Jersey City or Hoboken as alternative locations for Barstool HQ, which is currently based in an office in Manhattan.
“Honestly I’ve given that a lot of thought—and he’s definitely going to win—going to like Hoboken or Jersey City or something…” Portnoy said when asked about where he would move Barstool if, or when, Mamdani wins.
Again, however, Portnoy said that any plans to escape Manhattan are complicated by the fact that many of his employees are located in and around New York.
“But then we have all those people who are like, that f—s up their life just because I hate the guy. Like all the people in the New York office gotta go to Jersey City or they gotta go to Hoboken? So it’s a Catch-22,” he added, according to Whiskey Riff.
However, Portnoy hasn’t completely given up on the idea of closing his New York City office and moving, revealing that he has asked his “finance guy” to start looking at properties elsewhere.
“I may close the New York office. Trust me, I’ve given it a lot of thought. Because I can’t stand the thought of Mamdani running f–king New York City. I can’t stand it. But then a part of me’s like, how much will actually change?
“But I really have given it thought. I told our finance guy to start looking around for property. No joke. Take a principled stand. 30-something-year-old communist running New York City who’s never had a job in his life, hates America, doesn’t seem like the best.”
Portnoy has been an outspoken critic of Mamdani, 34, for months now, telling Fox News back in July that he believed the candidate—who is now the clear front runner in the race against Republican Curtis Sliwa and independent Andrew Cuomo—”hates capitalism” and would cause harm to the New York economy.
“It’s a very scary time,” Portnoy said. “I can’t believe that this guy may be the mayor of New York City.
“This is one of the worst, scariest candidates. He calls himself a democratic socialist, he’s not, he’s a socialist. He’s closer to a communist. He said it, he’s on the record saying he wants to put as many socialists in power so he can seize the means of production.”
Although his company is located in New York—for now—Portnoy himself has long been based outside of the city, spending his time traveling between his multiple homes, which are located in Florida, Massachusetts, where he was born and raised, and the Hamptons.
Just recently, the Barstool founder added an extraordinary new Florida dwelling to his already-impressive property portfolio, snapping up a $27.75 million mansion in the picturesque village of Islamadora.
Portnoy’s newest abode sits on a 1.65-acre waterfront lot and spans 10,228 square feet.
This “rare offering in the heart of the Florida Keys” features “150 feet of private waterfront, dockage, boat ramp, private beach, two pools, and lush, mature tropical landscaping,” the listing stated.
The sale set a record for Islamorada, a village that is made up of a string of six islands between the Atlantic and the Gulf of Mexico. The previous record of $22.65 million was set in 2023.
It was the second major real estate purchase Portnoy has made in the Sunshine State within the last five years, having also bought an enormous waterfront mansion in Miami back in 2021—when it had last been listed for $15 million.
The two-story contemporary features nine bedrooms and nine baths. It comes with a one-bedroom, one-bath guesthouse.
Built in 1939, the 6,000-square-foot home has since been restored and renovated. The lushly landscaped acreage includes a pool, patio, beach cabana, and private dock.
Although lavish, that home has since been plagued with mold issues, according to a post shared on Portnoy’s X account, where he asked his followers in August 2024 to recommend “the best mold company in the history of Miami” to come and look at his “moldy ass house.”
Back in his home state of Massachusetts, Portnoy opted not to buy in his home town of Swampscott, instead picking up two adjacent homes in Nantucket for $42 million in 2023.
According to multiple reports, the purchase set a record for the island and the state at the time. He reportedly spent an additional $2 million on furniture.
The price was more than worth it to secure a home in his “favorite place on Earth,” he said.
“Nantucket has always been my favorite place on Earth,” he wrote in a post on X. “The best day of my year was heading to the island for vacation. The worst day was taking the ferry back home.”
The two homes sit on 1.2 acres on the popular vacation isle: a 5,200-square-foot main residence and a two-bedroom guesthouse. There’s also a pool and harbor views for miles.
Perhaps the most intriguing feature of the home is its underground tunnel, which connects the guesthouse with a separate studio, both of which are separate from the enormous main residence.
And when the media mogul wants some R&R closer to his company’s New York office, he can head to his Montauk, NY, mansion, which he is understood to have purchased for $9.8 million in 2021.
The 5,700-square-foot vacation getaway in the trendy Hamptons enclave has five bedrooms, a pool, and endless ocean views.
Although reports surfaced that the cash-strapped owner was looking to sell the property for $14 million, he denied that he had put his Hamptons home on the market.