Trump, Mamdani set to meet again on mayor's home turf after months of political whiplash

President Donald Trump and New York City Mayor Zohran Mamdani will sit down Monday at Gracie Mansion, testing a budding working relationship even as the two remain deeply divided over immigration and other major policy fights.

Trump and Mamdani have continued to trade criticism while also finding areas where they can work together, most notably during a cordial February Oval Office meeting focused on New York housing. But their policy fights have continued, with Mamdani challenging Trump's immigration policies and Trump repeatedly criticizing the mayor's agenda.

"Sadly, Mayor Mamdani is DESTROYING New York! It has no chance!" the president wrote in April, a day after Gov. Kathy Hochul unveiled a proposal backed by Mamdani to impose a new tax on New York City second homes valued at more than $5 million.

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Trump first met with the socialist mayor last November and said Mamdani could "surprise some conservative people" and declared, "The better he does, the happier I am."

Their last meeting, on Feb. 26 at the Oval Office, was notably cordial, with Mamdani seeking Trump's support for an ambitious New York housing proposal despite their political differences.

"The new communist mayor of New York City, I think he's a nice guy, actually," Trump said in his State of the Union address in February. "I speak to him a lot. Bad policy, but nice guy."

Mamdani sought Trump's support in February for a massive housing project, calling their meeting "productive" as he pitched more than $21 billion in federal grants to build 12,000 affordable homes, along with parks, schools, health clinics and union jobs.

Trump is traveling to New York City this week for the United Nations General Assembly and is meeting with Mamdani ahead of the summit before returning to Washington on Wednesday, when Chinese President Xi Jinping is scheduled to arrive for a state visit.

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Trump and Mamdani have consistently clashed over immigration enforcement, with tensions intensifying after federal officials announced that ICE had arrested more than 2,100 people across New York during a monthlong operation dubbed "Operation Rotten Apple" as of earlier this month.

Mamdani's administration also joined a coalition lawsuit challenging a new Trump administration public-charge rule that rescinded Biden-era regulations governing how immigration officials assess an applicant's potential use of public benefits.

"If you are a citizen, or an individual seeking humanitarian relief like asylum, these changes will not affect you," Mamdani said at a news conference last week.

"The new public charge rule not only sweeps aside more than a century of established law, it is intentionally vague as a means of creating uncertainty and fear to isolate immigrant New Yorkers," he added.

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Mamdani is expected to speak to reporters after the meeting.

Fox News Digital reached out to the White House and the mayor's office for comment.