Trump goes to Gracie after blasting Mamdani’s tax push

The headline read “Trump to City: Let’s Build,” a deliberate reverse of the paper’s 1975 banner, “FORD TO CITY: DROP DEAD.” Mamdani was there to pitch 12,000 housing units over Sunnyside Yard in Western Queens.

That scene now leads to a third meeting, and the first on the mayor’s ground. Trump and Mamdani are scheduled to meet Monday, Sept. 21, 2026, at Gracie Mansion on Manhattan’s Upper East Side. Mamdani’s communications director, Anna Bahr, said the session will “focus on issues affecting New York City and New Yorkers.” Trump will be in the city that week to address the UN General Assembly, with remarks set for Tuesday, as New York hosts nearly 130 world leaders. Officials have released no agenda, timing, or press-access details.

The first meeting came in the Oval Office in November 2025, shortly after Mamdani defeated former Gov. Andrew Cuomo in the Democratic primary and won the mayoral election. During the 2025 campaign Trump had called him a “100% Communist Lunatic.” In the room the tone changed. Trump told reporters he would be “cheering” for Mamdani and called him a “very rational person.”

“I think you’re going to have, hopefully, a really great mayor. The better he does, the happier I am,” Trump said then. “There’s no difference in party, there’s no difference in anything. And we’re going to be helping him to make everybody’s dream come true. Having a strong and very safe New York.”

Mamdani has given that working relationship its fullest defense on NBC’s “Meet the Press.” He called it “honest, direct and productive.” He rooted the ease in a shared city: “New York City holds a very special place for him as well as for me. We’re both from the same city.” He said they were not shy about disagreement and still wanted to deliver on a shared reading of an affordability crisis for New Yorkers. On those terms, the mayor presents the partnership as practical politics between two natives who can wall off ideology long enough to talk housing and costs.

The same record shows where that claim meets hard policy. Earlier this year Mamdani rolled out a proposed pied-à-terre tax on New York City homeowners who keep a nonprimary residence in the city. Trump answered on Truth Social in blunt caps. “SO WRONG,” he wrote, then: “Sadly, Mayor Mamdani is DESTROYING New York! It has no chance! The United States of America should not contribute to its failure. It will only get WORSE. The TAX, TAX, TAX Policies are SO WRONG.” The post put the White House on record against federal contribution to a local tax turn Mamdani had just advanced. For the taxpayer outside the five boroughs, the stake is whether Washington underwrites the very revenue design the president called a path to failure.

Last week, six local governments led by New York City sued the Trump administration over a new green-card immigration rule. The filing arrived before the Gracie Mansion date. Border and immigration rules are federal. A city-led suit against a green-card measure places the government hosting the president in court against the administration he is meeting. The record carries no statement from the mayor’s office tying that litigation to Monday’s promised focus on New Yorkers’ issues.

Public safety cut through the February session as well. Mamdani raised with Trump the Department of Homeland Security arrest of a Columbia University student. The student was released shortly after the meeting. Trump’s November pledge had been specific: a strong and very safe New York, with the federal government helping. How City Hall treats federal enforcement when it reaches campus and street is part of that promise, not a side issue.

Mamdani has not retired the language he used before he won. He called Trump a despot and a fascist on the campaign trail. After the first Oval Office meeting he told “Meet the Press,” “That’s something I’ve said in the past and I say today.” The honest-and-productive description and the despot-and-fascist description both remain his. Trump’s shift from “100% Communist Lunatic” to “very rational person” sits beside the later Truth Social broadside on taxes. Neither man has erased the other’s record; they have only scheduled another room.

The Sunnyside pitch still hangs over the table. Twelve thousand units over a rail yard in Western Queens would need money, approvals, and time. Trump’s tax post ran the other way: the United States, he wrote, should not contribute to failure. Limited government and the taxpayer’s interest meet at that fork—whether federal dollars follow a mayor whose signature revenue idea the president has already branded “TAX, TAX, TAX” and “SO WRONG,” and whether a city suing the administration on green cards can expect smooth partnership on housing the next day.

Monday’s meeting is the third in-person sit-down and the first in New York. Trump speaks to the General Assembly on Tuesday.