NEW YORK (AP) — Across the U.S., calls to “tax the rich” have become potent political slogans. But even in Mayor Zohran Mamdani’s New York, getting the wealthy to pay more isn’t playing out as smoothly as supporters hoped.

What seemed at first like an easy idea — slapping a new tax on people who own luxury second homes in the Big Apple but live elsewhere most of the year — has instead created a lot of confusion in the city’s notoriously convoluted world of real estate arrangements.

“It seems very simple but the more you dig into it, the more nuances you look at, the more complicated it gets,” said Gary Bingel, a state and local tax expert and partner at EisnerAmper, an accounting firm.

It has also prompted pushback from both the city’s very wealthy and the merely moderately wealthy.

President Donald Trump, whose gilded Manhattan penthouse could be subject to the tax since his primary residence is now in Florida, said he was looking into whether federal intervention could “avert this disaster, before it is too late.”

A group of homeowners sued over the city’s rollout of the tax, arguing that officials had not done enough to figure out who would have to pay the tax and instead made it property owners’ responsibility. A judge temporarily paused the process this week, but the city moved to appeal, allowing the tax effort to continue until it’s sorted out in court.

Securing a new tax on multimillion-dollar second homes, known as pied-à-terres, was an early win for Mamdani in his quest to raise taxes on the city’s highest earners to pay for his ambitious liberal agenda.

The so-called pied-à-terre tax would levy a new surcharge on one-, two- and three-family homes valued at more than $5 million, as well as condos and co-ops valued at $1 million or more, if those dwellings are not a person’s primary residence.

The idea, according to officials, would bring $500 million to the city’s coffers annually, paid primarily by bigwigs who get to enjoy city life but don’t pay city income taxes.

That’s where things start to get hairy.

It’s common for high rollers to place their properties in trusts, obscuring ownership while allowing the property to pass more easily to family members. Limited liability companies can similarly shield an owner’s identity, also making it hard for government officials to tell who actually lives in any given apartment.

From there, there are numerous arrangements that can complicate who would be subject to the tax. For example, letting a distant family member stay at a second home without formal documentation, or if someone owns one or more properties and rents them out, but the tenants don’t have documentation that the unit is their primary residence.

“Those situations make it difficult to prove people are in there,” said Mark Limardo, a partner at the law firm Herrick in Manhattan who focuses on taxes. “The concept is simple, but the ownership rules and the documentation rules have made it very complicated.”

Outcry and litigation
City Hall, for its part, argues that it shouldn’t be difficult to provide proof that someone actually lives in the city and says that its finance department is experienced in parsing tangled webs of paperwork.

Mamdani, no stranger to razzing wealthy people, debuted the tax with a video singling out hedge fund CEO Ken Griffin by standing outside a Manhattan penthouse the billionaire purchased for around $239 million. The clip sent Mamdani’s supporters swooning, but Griffin later said it was “frightening” that a public official would call attention to one of his homes, especially after the killing of UnitedHealthcare CEO Brian Thompson in the same neighborhood.

The city then published an expansive online list of property owners who it said could be subject to the tax, listing their names, addresses and property values. The list, which the city is legally required to publish, inflamed tensions between the mayor and the city’s wealthy, many of whom argued the roll amounted to doxing or public shaming.

The administration has mailed notices to a much smaller group — about 17,000 properties — that it suspected would be subject to the tax, telling them they could apply for exemptions. Mamdani announced the mailers in a celebratory social media post that read: “If you have a second home in New York City worth more than $5M, check your mailbox when you’re back in the five boroughs — because you’ve got mail.”

He later pushed back the deadline for exemption requests following public outcry from people who claimed to have received the letters in error or had trouble navigating the process.

Stewart Sterk, a real estate law professor at Cardozo School of Law in New York, predicted last week’s lawsuit wouldn’t be the last, saying he expected many of the targets of the tax to file individual cases over denied exemptions, given the vast number of apartments at play and the various arrangements people have connecting them to their properties.

“This is going to be a subject of litigation for quite a while,” he said.