'Beyond insane': Kevin O'Leary blasts Mamdani's tax-the-rich plan, says NYC mayor is becoming Miami's best real estate agent. Protect your money now

O’Leary was specifically referring to proposed tax increases on new York’s wealthiest driving millionaires and more to Florida. In a press briefing unveiling his preliminary budget, Mamdani said that if he’s unable to persuade Gov. Kathy Hochul to raise taxes on the wealthy he could be forced to raise property taxes by 9.5% (2).

Now, at May 7 press conference, Hochul’s office has announced the state’s 2027 budget (3). Notably, it featured Mamdani’s signature pied-à-terre tax on investor properties and second homes with a value of over $5 million, which is expected to generate $500 million in annual revenue. However, the budget also didn’t “raise income or statewide business taxes.”

It remains to be seen how this will impact Mamdani’s 9.5% option of last resort, but it seems to be a bit of good news for a beleaguered Big Apple.

If Mamdani still raises property taxes, it would affect more than 3 million residential units and over 100,000 commercial buildings across the city (4). He acknowledged the move would not only hit wealthy residents, but “effectively be a tax on working- and middle-class New Yorkers who have a median income of $122,000 (2).”

O’Leary didn’t hold back when reacting to the original proposal.

“This is bat poopoo crazy,” he said, adding that, rather than cut spending, Mamdani will simply “tax you into oblivion.”

He also argued the policy could accelerate an ongoing migration trend out of high-tax jurisdictions — particularly toward Florida, where he lives.

“Probably sometime next year, within 12 to 18 months, I will meet him in Miami and give him real estate agent of the year award,” O’Leary quipped. “I live in Miami Beach. Everybody from New York and New Jersey and Massachusetts is moving into my neighborhood. I’m pissed off and this guy's just doing more of it.”

According to real estate developers, that trend was already gaining momentum even before Mamdani took office.

In the months leading up to New York City’s mayoral election, Isaac Toledano, CEO of Miami-based developer BH Group, said his firm closed more than $100 million in signed contracts from New York buyers — about twice the year-earlier volume, according to prior reporting from Moneywise.

The New York-to-Miami real estate landscape

Do the facts really bear out O’Leary’s taunting claim that Mamdani is Florida’s best real estate agent? Not so fast, according to a report from the New York Post (5). As of April 2026, while New Yorkers have kept pace with the ‘moving to Florida’ trend that started during the pandemic, most of these are hedging their bets when it comes to real estate.

“Uncertainty kept high earners renting,” Jiayi Xu, senior economist at Realtor.com, told the Post, explaining that most of these new arrivals were unsure how long they’d stay in Florida. Added to this, inflated home prices made even high earners wary of buying.

“High-income, price-insensitive tenants who’d rather pay a premium than commit to a purchase” found that buying a starter home in Miami would cost $3,540 monthly — and renting would cost only $2,511 a month, according to Xu’s calculations.

‘An obligation to pay as little tax as possible’

Mamdani campaigned heavily on the promise to raise income taxes on the wealthiest New Yorkers. On a broader scale, whether America’s ultra-rich are paying their fair share of taxes is an issue that has long been debated.

In fact, Mamdani recently made an example of one of New York’s wealthiest, filming a social media post outside billionaire and Citadel CEO Ken Griffin’s $238 million penthouse at 220 Central Park South to explain why the public should support his tax plan (6). The Citadel CEO said in response, “to turn me into a political puppet was just in poor taste, really poor taste (7).”

“What really upset me about the video was the fact that it put me in harm’s way,” Griffin said. “He seems to have forgotten that the CEO of another American company was assassinated just blocks from where I live in New York.”

Now, Citadel is doubling down on Florida by expanding its offices there, according to Reuters (8).

Most of the ultra-rich, like Griffin, build their wealth through assets and deep connections to their companies — not wages; as the value of these assets rises, their net worth grows.

However, the U.S. tax system isn’t designed to fully capture those gains. Capital gains are typically taxed at lower rates than regular income, and taxes aren't owed until the assets are sold.

In fact, as NYU Stern professor Scott Galloway once put it, if you’re trying to build wealth, you have “an obligation to pay as little tax as possible.”

One asset class America’s wealthy have relied on for decades is real estate — in part because of the generous tax treatment it receives.

When you earn rental income from an investment property, you can claim deductions for a wide range of expenses, such as mortgage interest, property taxes, insurance and ongoing maintenance and repairs. This is part of the ultra-rich’s secret for capturing as much wealth as possible while minimizing tax exposure.

Real estate investors also benefit from depreciation — a tax deduction that recognizes the gradual wear and tear of a property over time. Investors can also use tools like refinancing and 1031 exchanges to keep their capital compounding instead of cashing out.

Today, you don’t need to be able to afford a $238 million New York apartment — or buy a starter home outright — to invest in real estate. Crowdfunding platforms like Arrived offer an easier way to get exposure to this income-generating asset class.

Backed by world-class investors like Jeff Bezos, Arrived allows you to invest in shares of rental homes with as little as $100 — all without the hassle of mowing lawns, fixing leaky faucets or handling difficult tenants.

The process is simple: Browse a curated selection of homes that have been vetted for their appreciation and income potential. Once you find a property you like, select the number of shares you’d like to purchase and then sit back as you start receiving any positive rental income distributions from your investment.

For a limited time, when you open an account and add $1,000 or more, Arrived will credit your account with a 1% match.

Mogul is another option for those with more cash available to invest or who are already comfortable with real estate investing. It’s a real estate investment platform offering fractional ownership in blue-chip rental properties, which gives investors monthly rental income, real-time appreciation and tax benefits — without the need for a hefty down payment or 3 a.m. tenant calls.

Founded by former Goldman Sachs real estate investors, the team hand-picks the top 1% of single-family rental homes nationwide for you. In other words, you gain access to institutional-quality offerings for a fraction of the usual cost.

Each property undergoes a rigorous vetting process, requiring a minimum 12% return even in downside scenarios. Across the board, the platform features an average annual IRR of 18.8%. Offerings often sell out in under three hours, with investments typically ranging between $15,000 and $40,000 per property.

You can sign up for an account and then browse available properties here.

Keep more of what you earn

The wealthy don’t just focus on what they invest in — they also pay close attention to where those investments sit. Using tax-advantaged retirement accounts can be a powerful way to keep more capital compounding over time.

For seasoned investors with portfolios of $50K or more, you might consider diversifying your nest egg through a flat-fee self-directed retirement account.