By: Hal C Clarke

For generations, New York has been synonymous with ambition, opportunity and wealth creation. Yet as The New York Post has repeatedly chronicled, it has also become synonymous with something far less glamorous: one of the most aggressive and unforgiving tax enforcement regimes in the United States. Now, with Mayor Zohran Mamdani pushing a new round of tax increases aimed squarely at the city’s highest earners, experts warn that Albany and City Hall are preparing to tighten the vise even further on residents who dare to consider escape.

The stakes are enormous. High-income New Yorkers have long flirted with relocation to Florida, Texas, Tennessee and other low-tax states. But as The New York Post has detailed in a series of investigative reports, severing financial ties to the Empire State is far more complicated—and far more perilous—than most taxpayers imagine. The widely cited “six-months-and-a-day” rule, which treats anyone spending 184 days or more in New York as a statutory resident, is only the beginning of a labyrinthine process that can ensnare even the most well-intentioned expatriates.

To the uninitiated, tax residency appears simple. Spend less than half the year in New York, establish a home elsewhere, and presto—freedom from state and city income taxes. Yet according to tax professionals interviewed by The New York Post, that belief is one of the most expensive misconceptions in modern finance.

In reality, auditors apply a sweeping “domicile” test that examines nearly every aspect of a taxpayer’s life. Where is one’s primary home? Where are bank accounts maintained? Which state issued the driver’s license? Where are family members, social clubs, professional licenses and medical providers located? Even sentimental items—art collections, heirlooms, photo albums—can be scrutinized as evidence of a lingering New York connection.

“New York is an extremely aggressive state when it comes to state income taxes,” Christine Concepcion, a veteran tax attorney, told The New York Post. “They do not like people leaving, and they will do whatever they can to trap you back into the New York tax net.”

The comment reflects a widespread consensus in the accounting and legal communities: once New York decides to audit a departing resident, the burden of proof is overwhelmingly on the taxpayer. And the state has grown increasingly creative in how it defines proof.

Those enforcement tactics are poised to intensify if Mayor Mamdani succeeds in advancing his signature proposal: a 2% income tax surcharge on millionaires. As The New York Post has reported, the plan would raise the city’s top income tax rate to 5.9%, on top of New York State’s already steep brackets. When combined with federal taxes, many high earners could face marginal rates approaching 60%—among the highest in the developed world.

For Mamdani, the tax hike is framed as a matter of social justice and fiscal necessity. For the city’s business class, it is viewed as an open invitation to leave.

Experts interviewed by The New York Post say that any new revenue generated by the tax increase will almost certainly be accompanied by expanded enforcement budgets. More auditors, more investigations, and more aggressive residency challenges are widely expected.

Tatiana Tsoir, an accountant and CEO of Linza Advisors, offered a blunt assessment to The New York Post: “You increase the taxes and you also allocate more money to enforcement.” Drawing on her upbringing in Belarus, she compared the approach to tactics used by authoritarian governments to squeeze revenue from a captive population.

The perils of underestimating New York’s tax apparatus were laid bare in a case highlighted by The New York Post involving Jon Hoff and his wife, Kathleen Ocorr-Hoff. The couple believed they had done everything right when they purchased a $1 million condominium in Naples, Florida, with the intention of making it their primary residence.

They registered to vote in Florida, obtained Florida driver’s licenses, moved valuable possessions south, and even acquired local hunting and fishing permits. They opened businesses in the Sunshine State and spent substantial time there.

Yet New York auditors pounced. The couple had continued to cash paychecks in New York and maintained memberships at local country clubs—details that, in the eyes of the state, proved that their “center of life” remained firmly north of the Mason-Dixon line. The result: a $60,000 tax bill.

Their legal challenge failed, a cautionary tale that The New York Post described as emblematic of how little room for error exists in the system.

Another weapon in New York’s arsenal is the so-called “convenience of the employer” rule, one of the most controversial provisions in American tax law. As The New York Post has explained, the rule allows New York to tax income earned by individuals who live elsewhere but work remotely for New York-based companies—unless the employer explicitly requires them to work outside the state.

Andrew Wilford of the National Taxpayers Union Foundation told The New York Post that the implications are often absurd. Even a single day spent in a New York office—perhaps to attend a meeting or holiday party—can trigger tax liability for an entire year.

In the post-pandemic era of hybrid work, the rule has become a major source of anxiety for executives who believed they had successfully relocated. Many discover only during an audit that their tax exposure never truly ended.

When New York auditors go hunting for revenue, nothing is off limits. The New York Post has reported that investigators routinely examine where children attend school, where doctors are located, where religious services are attended, and where pets are groomed. They ask where family photographs hang, where cars are garaged, and even where a taxpayer intends to be buried.

The objective is to determine the elusive “center of life.” If that center remains in New York—even in subtle ways—the state feels justified in treating the individual as a resident regardless of time spent elsewhere.

Such scrutiny has earned New York a reputation, in the words of one accountant quoted by The New York Post, as “the IRS on steroids.”

And yet, despite the formidable obstacles, New Yorkers continue to flee in record numbers. The New York Post reported that between 2021 and 2024, nearly 900,000 residents left the state. On average, a net resident departs every two minutes and 23 seconds.

The exodus has real fiscal consequences. The National Taxpayers Union Foundation estimates that New York will collect $3.8 billion less in tax revenue in 2025 because of population losses—a figure that threatens to undermine the very social programs Mamdani hopes to expand.

High earners are especially mobile. Many financial professionals, entrepreneurs and retirees calculate that the savings from lower taxes in Florida or Texas can reach hundreds of thousands of dollars per year. For them, the risk of an audit is simply part of the cost-benefit analysis.

Yet as The New York Post has observed, many would-be tax refugees undermine themselves through poor planning. They keep a pied-à-terre in Manhattan, retain New York social memberships, or fail to fully shift their professional footprint. Some continue to see New York doctors or store prized belongings in local safe-deposit boxes.

Each oversight becomes ammunition for auditors determined to preserve the state’s tax base.

The message from experts is consistent: leaving New York requires more than a change of address. It demands a wholesale reinvention of one’s personal and professional identity.

With Mamdani’s tax agenda looming and Albany’s enforcement machinery already running at full throttle, the battle between fleeing taxpayers and state auditors is entering a new, more intense phase. The New York Post has portrayed the conflict as a high-stakes chess match in which the house holds nearly every advantage.

For wealthy residents contemplating departure, the calculus is increasingly stark. Remain in New York and face some of the highest tax rates in the nation—or attempt to escape and risk years of audits, legal fees and potential penalties.

For city leaders, the gamble is equally fraught. Raise taxes too high, and the golden geese may simply fly away. Crack down too hard, and the state risks reinforcing its image as inhospitable to prosperity.

As The New York Post has made clear, the coming years will test whether New York can continue to finance its expansive ambitions without driving away the very people who pay the bills.

One thing, however, is certain: in the Empire State, leaving is never as easy as it looks—and the taxman is always watching.