Kevin O'Leary wants to know how many ways one tax proposal can be wrong. The "Shark Tank" star and venture capitalist tore into a plan linked to New York City's Zohran Mamdani that would slap an annual surcharge on luxury second homes valued at more than $5 million, a measure supporters say could raise roughly $500 million a year to close the city's budget deficit.
O'Leary's verdict, delivered on Fox Business, was blunt. As the Daily Mail reported:
"Let me count how many ways this policy is stupid... You want more of these people... That don't live here, pay taxes, pay maintenance, create jobs... And don't use the city's services."
His argument is straightforward: wealthy non-residents who own luxury apartments in Manhattan pay property taxes, fund building maintenance, employ doormen and contractors, and consume almost none of the city's public services. Punishing them with a new surcharge doesn't close a budget gap. It opens the door.
Mamdani made his pitch in a viral video filmed outside Ken Griffin's $238 million penthouse at 220 Central Park South, the purchase that broke the record for the most expensive home sale in the United States when Griffin bought it in 2019. Standing on the sidewalk, Mamdani pointed up and promoted his proposed tax on properties "like this penthouse."
The stunt drew immediate backlash. CNBC anchor Sara Eisen fired back, noting Griffin's broader footprint in the city:
"Ken Griffin employs thousands of people in NYC and is planning to build the tallest office tower on Park Ave., investing billions more and creating thousands more jobs."
Hedge fund manager Dan Loeb called the video "childish" and warned it could damage jobs and tax revenue. The reaction from the financial world was not subtle: Citadel LLC, Griffin's firm, recently revealed it is reconsidering its planned redevelopment of 350 Park Avenue. That project alone would have poured billions into Manhattan's commercial real estate market and created thousands of construction and office jobs.
Griffin himself relocated his hedge fund's headquarters to Miami in 2022. His primary residence is now in Florida. The penthouse Mamdani used as a political prop belongs to a man who has already demonstrated exactly how easy it is to leave.
O'Leary's critique didn't stop at the specifics of one penthouse or one billionaire. He framed the proposal as part of a broader economic mistake New York keeps making. As the New York Post reported, O'Leary argued that outside investors help fund development, pay taxes, and support maintenance jobs while placing little demand on city services.
"They spend millions, they employ people, they maintain properties, that's economic activity the city needs."
In recent years, a growing number of high earners and businesses have relocated from high-tax states like New York and California to lower-tax regions such as Florida and Texas. Firms and high-net-worth individuals have increasingly signaled a willingness to move capital in response to tax policy. The trend is not theoretical. It is happening, and New York is on the losing end of it.
The proposed pied-à-terre surcharge targets exactly the class of investor most mobile, most capable of relocating, and least dependent on any single city. These are people who chose New York. They can unchoose it with a phone call to a real estate broker.
The tax plan does not exist in a vacuum. Mamdani's political brand has drawn sharp criticism from figures well beyond Wall Street. Bill Maher recently made the case on his show that Mamdani is a communist, and his guest struggled to answer the charge.
Mamdani has embraced the label of democratic socialist, though his track record in office has not matched his rhetoric. His biggest promises have stalled even as he insists the ideology "can flourish anywhere," a claim that has drawn skepticism from observers tracking his stalled agenda.
The ideological pressure on Mamdani runs in both directions. Communist groups have urged him to break entirely with the Democratic Party and build a new workers' party, a move that would place him even further outside the mainstream of New York politics. That pressure from actual communist organizations underscores how far left the policy conversation has drifted in City Hall.
And Mamdani's public confrontations have not always gone according to plan. He talked tough about King Charles ahead of a meeting, then shook the monarch's hand and said nothing. The pattern is familiar: bold rhetoric aimed at easy targets, followed by retreat when consequences arrive.
Supporters of the surcharge say it would generate around $500 million annually to help close New York City's budget deficit. That number assumes the tax base holds still, that the wealthy owners of $5-million-plus second homes simply absorb the new cost and keep writing checks.
Griffin's own trajectory tells a different story. He bought the penthouse in 2019. By 2022, he had moved his hedge fund and himself to Florida. Now Citadel is rethinking a major Manhattan development. The timeline is a case study in how tax hostility produces capital flight, not revenue.
O'Leary put it plainly on Fox News, where he warned about what Mamdani's approach could mean for the city's future. The concern is not abstract. It is measured in office towers that don't get built, in jobs that don't get created, and in tax revenue that migrates south.
The broader backlash against socialist economics within Democratic circles is not limited to New York. Sen. John Fetterman recently condemned May Day protests and warned of communist drift in his own party, a sign that even some Democrats recognize the political and economic danger of the hard left's policy instincts.
The people who would bear the real cost of this proposal are not billionaires with penthouses on Central Park South. They are the doormen, maintenance workers, contractors, and service employees whose livelihoods depend on wealthy non-residents continuing to invest in New York City real estate. They are the small businesses in neighborhoods sustained by luxury spending. They are the taxpayers left holding a larger share of the city's obligations when the revenue base shrinks.
Eisen's point about Griffin was not just a defense of one man. It was a statement about incentives. A single investor planning the tallest office tower on Park Avenue represents billions in construction spending, thousands of jobs, and decades of property tax revenue. Threaten that investor on camera, and the tower may never rise.
O'Leary called the policy economically reckless. Loeb called the video childish. Citadel started reconsidering its plans. The market is already answering the question the city's leaders refuse to ask.
New York can keep chasing the rich out of town and calling it justice. But the bill always lands on the people who can't afford to leave.
