And when Kimmel finally suggested sending Trump a selfie from the set, Mamdani shut the idea down.
“Jimmy, I love you, but I love housing more.”
It was a revealing exchange between two figures on the political left — and it showed just how differently Mamdani is approaching Trump now that he has a city to run.
Kimmel Keeps Coming Back to Trump
Kimmel seemed fascinated by the relationship between the two New Yorkers.
“Did you guys hit it off immediately or is it something that you really went into thinking, like, ‘Okay, I need to have a relationship with the President of the United States and I think the best way to do it is to charm him?’ How did you do that and can you help me?”
Mamdani laughed before offering a short response.
“Sorry brother.”
But rather than launching into an attack on Trump, the mayor explained why he has kept communication open with the White House.
“Look, the president and I have many disagreements. One thing we do agree on is this city, how much we love this city.”
That answer set the tone for the rest of the conversation.
Mamdani said he decided from his first meeting with Trump that their discussions should focus less on their personal political differences and more on what Washington and City Hall might actually accomplish for New Yorkers.
The mayor specifically pointed to Sunnyside Yard, the massive Queens redevelopment proposal that could produce roughly 12,000 homes and 30,000 jobs.
“The number one thing that we’ve been speaking about recently has been Sunnyside Yard, which is this idea for decades of building a platform over a rail yard and then building 12,000 homes.”
For Mamdani, maintaining access to the president apparently matters more than scoring an applause line on late-night television.
Then Kimmel Asked About the Text Messages
The conversation became even more interesting when Kimmel turned to reports that Mamdani and Trump communicate directly.
Mamdani confirmed that the two occasionally text.
“From time to time we’re in communication, and it’s about Sunnyside Yard, and it’s about how we can deliver for the city.”
Kimmel wanted to know what Trump’s messages looked like and whether the president communicated with Mamdani the same way he writes on social media.
Mamdani characterized the exchanges as fairly ordinary.
That prompted Kimmel to marvel at how far the mayor apparently had gotten with Trump.
“Wow. You really have broken through with him.”
Kimmel then joked that Mamdani might be needed in Washington to spend his days hanging around the Oval Office.
But the host wasn’t finished.
He floated the possibility of Mamdani sending Trump a selfie of himself and Kimmel from the television set.
Mamdani wasn’t interested.
“Jimmy, I love you, but I love housing more.”
The audience laughed, but there was a serious political calculation underneath the joke.
Trump and Mamdani Have Found an Unlikely Working Relationship
Nobody would have predicted this partnership from the rhetoric of the 2025 mayoral campaign.
Trump fiercely criticized Mamdani’s politics and backed Andrew Cuomo in the New York City mayoral contest.
But after Mamdani won, the tone between the two men changed.
Trump met Mamdani at the White House and publicly suggested the mayor could exceed conservatives’ expectations.
“The better he does, the happier I am.”
Their ideological disagreements certainly haven’t disappeared.
Trump even referred to Mamdani as “the new communist mayor” during his February State of the Union address before adding something unexpected.
“I think he’s a nice guy, actually. I speak to him a lot. Bad policy, but nice guy.”
That strange political relationship continued in September when Trump met Mamdani at Gracie Mansion.
Following that meeting, Mamdani said his discussions with the president centered on affordability, economic growth and ways the federal government could work with New York City.
The two men remain far apart on immigration, economics and numerous other major issues.
Yet neither appears eager to completely sever the relationship.
Mamdani Wasn’t Going to Sacrifice Access for a Late-Night Joke
That was ultimately what made the Kimmel interview noteworthy.
Mamdani had every opportunity to use a friendly television audience to attack Trump personally.
He didn’t.
Instead, he repeatedly redirected the discussion toward housing and governing New York City.
Whatever anyone thinks about Mamdani’s left-wing agenda, the mayor appears to understand one basic reality of his new job: New York City has plenty of reasons to maintain a functional relationship with the federal government.
Picking a needless fight with the president on national television might produce a viral clip.
It doesn’t build 12,000 homes.
Kimmel kept searching for the joke.
Mamdani kept returning to Sunnyside Yard.
And when the host finally tried to bring Trump directly into the bit with a selfie, the mayor drew the line.
For one night on late-night television, the democratic socialist mayor wasn’t interested in playing the familiar anti-Trump game.
He had business with the White House to protect.
