When Zohran Mamdani, the mayor of New York City, boarded a flight to Washington early Thursday morning, he wore a dark hat and a face mask to obscure his identity.
He had reason for secrecy. He was on his way to the White House for an unannounced meeting with President Trump, who has repeatedly gone to battle with Democratic cities like the one Mr. Mamdani runs.
Yet by the time the mayor emerged from the Oval Office hours later, he was ready to crow, claiming not one but two wins from a president who rarely gives them to political adversaries.
First, Mr. Mamdani posted a photo of the two men behind the Resolute Desk, saying that they had discussed working together on a major project to build housing in New York. In the photo, a grinning Mr. Trump held up a mock New York Daily News front page Mr. Mamdani had given him, featuring a flattering photo of the president and the blaring headline “Trump to City: Let’s Build.”
A few minutes later, the mayor posted again to say that Mr. Trump had just called him and promised that federal immigration agents would release a detained Columbia University undergraduate after Mr. Mamdani had brought up her case in the meeting.
“He has just informed me that she will be released imminently,” Mr. Mamdani wrote on social media, referring to the student, Elmina Aghayeva, a senior from Azerbaijan who had been arrested earlier Thursday. Columbia later confirmed that she had been freed.
It was the latest remarkable turn in one of the most unlikely relationships in American politics — one that has seen two men at opposite ends of the political spectrum, who have every reason to openly clash, tentatively find common ground instead.
Only months ago, Mr. Trump was painting a dire picture of what would happen to New York if Mr. Mamdani, a 34-year-old democratic socialist he incorrectly calls a “communist,” was elected. The mayor was calling Mr. Trump a “despot” and his allies were tensely preparing for the president to flood the city with immigration agents and National Guard troops and provoke a crisis.
Of course, Mr. Trump, 79, is famously erratic, and it remains anyone’s guess how long his apparently friendly relationship with Mr. Mamdani will last. Details about where and how the housing might actually be built were not immediately forthcoming, and it was not clear how much Mr. Mamdani’s intervention drove the administration’s decision to release Ms. Aghayeva.
The White House did not comment on the meeting, and neither the mayor nor the president spoke to reporters at the White House.
But for the second time in just a few months, a president who is menacing other Democratic leaders seemed to roll out a welcome mat in the Oval Office for Mr. Mamdani, and the two appeared to leave on good terms.
Political observers on both sides of the aisle were once again riveted, and Republicans who have tried to vilify Mr. Mamdani could only speculate about Mr. Trump’s motives.
“It’s kind of a remarkable thing to see again in action in the second meeting,” said Ana María Archila, the departing co-director of the New York Working Families Party, whom Mr. Mamdani recently named his international affairs commissioner.
She added, “The president tends to consider Democrats as absolute adversaries, and somehow Mamdani pierces through that approach in ways that are very surprising.”
Joe Borelli, a former Republican councilman turned lobbyist from Staten Island, said Mr. Mamdani clearly “knew his audience” when he entered the Oval Office bearing a Daily News mock-up featuring the president’s visage.
In many ways, it was less surprising that the two men might find a way to work together on housing and construction. Mr. Mamdani took office vowing to address New York’s affordability crisis, in part by building more housing. Mr. Trump first made his name as a Manhattan real estate developer.
“He came to the president today with a couple of pitches that would produce and construct more housing in a handful of projects than has happened in 50 years,” Anna Bahr, a spokeswoman for City Hall, said.
In the photo Mr. Mamdani posted, Mr. Trump is pictured holding two printouts of Daily News front pages, one real and one fake.
The one in his left hand shows an actual front page from 1975, with the infamous headline “Ford to City: Drop Dead.” It was published after President Gerald Ford refused to bail out New York City, which was nearing bankruptcy.
The fake front page, which Mr. Trump holds in his right hand, credits Mr. Trump with backing a “New Era of Housing.”
The page contains some potential clues about what that might mean. In smaller type beneath the headline, the page reads “Trump Delivers 12,000+ Homes; Most Since 1973.”
Ms. Bahr declined to provide any further detail, but that is possibly a reference to Sunnyside Yards, the enormous rail yard in Queens over which the city has long dreamed of building 12,000 units of housing.
“It’s clearly the most feasible site for large-scale development,” said Alicia Glen, the deputy mayor in former Mayor Bill de Blasio’s administration who helped craft a master plan for the site.
The two men’s exchanges on immigration, however, were significantly more surprising.
Mr. Trump, the leader of the right, has overseen one of the most restrictive and heavy-handed anti-immigrant crackdowns in modern American history. Mr. Mamdani, himself an immigrant from Uganda, has fully embraced New York City’s status as a haven for immigrants and has portrayed Mr. Trump’s deportation agenda as a cruel abuse of power.
On Thursday, Mr. Mamdani came to the meeting with a list of five people from the New York City area with ties to Columbia University who had been detained by immigration authorities, and asked that the cases against them be dropped, according to Ms. Bahr.
The list included Ms. Aghayeva, Mahmoud Khalil, Yunseo Chung, Mohsen Mahdawi and Leqaa Kordia.
Ms. Aghayeva was arrested Thursday morning on Columbia’s Manhattan campus around the time Mr. Mamdani was headed to the airport. The university accused Immigration and Customs Enforcement agents of gaining access to the campus under false pretenses, but federal agents said that she was studying in the country on a visa that was terminated in 2016.
Mr. Trump appeared to yield to Mr. Mamdani’s entreaties regarding her case, though he has previously gone to great lengths to defend the actions of federal agents, even when they have killed American citizens.
Ms. Bahr said that Thursday’s meeting stemmed from the last one, when the president asked the mayor to come to him “with ideas of big things that they could build together.” The housing proposal, she said, was an example of one such idea.
Mr. Mamdani and Mr. Trump were joined at the meeting by Elle Bisgaard-Church, the mayor’s chief of staff, and Susie Wiles, the president’s chief of staff, Ms. Bahr said.
Their first meeting came shortly after Mr. Mamdani won the mayoral election in November. Despite their vast political differences, Mr. Trump expressed optimism at the time about Mr. Mamdani’s coming mayoralty, and Mr. Mamdani voiced appreciation for the president’s willingness to discuss areas of overlapping concern.
Earlier this week, during his State of the Union address, Mr. Trump said he spoke often to Mr. Mamdani and described him as a “nice guy,” even if he embraced “bad policy.”
He also singled out New York City’s use of volunteer emergency shovelers to help clean up after this week’s snowstorm. The city asked the shovelers to provide two forms of identification, a federal requirement that Republicans who support voter identification laws have nevertheless seized on as evidence of hypocrisy.
For his part, Mr. Mamdani has largely avoided directly criticizing Mr. Trump, who wields substantial control over federal funding streams that New York relies on. One deviation from that stance came in January, after the U.S. military’s capture of Nicolás Maduro, the Venezuelan leader, which Mr. Mamdani described as “an act of war and a violation of federal and international law.”
Bill Cunningham, who was the communications director for former Mayor Michael R. Bloomberg, warned Mr. Mamdani against being “lulled into a false sense of security.”
“With Trump,” he added, “you never know where his mind is going.”
Jeffery C. Mays contributed reporting.
Dana Rubinstein covers New York City politics and government for The Times.
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