Trump & Socialist NYC Mayor Shock Nation With Secret Texts, Break Decades of Ice

Paul Riverbank, 1/14/2026Trump and NYC's socialist mayor forge unlikely, pragmatic alliance—beyond ideology, toward city gain.

Twice each week, sometimes more, messages pass between the Oval Office and City Hall. Their chatter, described as “cordial, even warm” by aides from both camps, vacillates between national headlines and the city’s perennial headaches. “They talk weather, sports, the UN, even the best bagel shops,” recalls one person close to the matter. No one’s pretending they’re best friends. But after years of frosty exchanges between the federal government and Gotham, this is a break from the script.

Their relationship began back in November, behind closed doors, watched keenly by staffers expecting fireworks. The air, however, changed in an instant. President Trump, never one to shy from banter, greeted his counterpart with a grin and a quip: “You’re taller in real life — TV must have bad angles,” he joshed, provoking laughter rather than stand-offish posturing. Those initial moments, according to someone present, set a tone nobody saw coming.

Over lunch, the banter continued. At one point, the mayor branded Trump a “fascist”— with a wry smile, sources say. The President responded with an amused pat on Mamdani’s jacket, sidestepping any hint of offense. Fast forward a few days, and a photo of Trump in an unexpectedly chic burgundy scarf — not dissimilar to one the mayor wore — circulated on social media. The city was quick to notice, and commentators archly asked if the President was taking fashion cues from his political opposite.

Camaraderie, though, isn’t carte blanche. Serious divides crop up, as with the U.S. raid that led to Venezuelan leader Nicolás Maduro's arrest. Within hours, Mamdani picked up the phone to register disapproval. “I thought it was quick for him to be criticizing,” Trump would later tell a reporter, a touch of bewilderment in his retelling. “We get along, but I figured I’d get a month’s grace, at least.” Their rapport survives these barbs, perhaps because both sides keep sight of what’s at stake.

Observers point to shrewd calculation as much as genuine warmth. One longtime city hall operator put it bluntly: “If you’re New York’s mayor and the White House holds purse strings, pragmatism beats grandstanding.” Federal dollars, after all, loom large over city budgets, and no mayor can afford to gamble away access—especially with Washington threatening to withhold funds from so-called “sanctuary cities,” a group in which New York firmly plants its flag.

The dynamic extends to tricky policy disagreements. Trump, never subtle on social media, took a sledgehammer to congestion pricing plans, calling them an “unmitigated DISASTER” and demanding an immediate halt — claims at odds with first-wave data hinting at cleaner air and less traffic. That headline-grabbing rhetoric is complicated terrain for the mayor: he needs to defend the policy without weakening the relationship that keeps federal money — and influence — coming his way.

Not everyone finds the arrangement strange. Andrew Kirtzman, a seasoned strategist and no stranger to city politics, notes that “Trump despised Bill de Blasio, wrote off much of the city for years. Suddenly, he appears to relish this new chapter. Mamdani must wake up surprised by it all.” Perhaps each man benefits: the President, recasting himself as engaged with his hometown after bruising local feuds; the Mayor, gaining a direct channel for advocacy and negotiation few predecessors ever enjoyed.

On the ground and online, the mayor’s most vocal allies aren’t crying betrayal. Most see the unusual dialogue as smart politics, an exercise in maneuvering rather than capitulation. For now, transactional logic prevails. Neither side needs to advertise affection for the other; access, negotiation, and practical gain are enough.

It has been a long time since New York City politics saw anything quite like this — a socialist mayor and a conservative president, keeping things civil and even, on odd occasions, lighthearted. The boundaries of ideology remain sharply drawn, but between the power centers of the city and the country, the communication lines have rarely been more open. Where this détente leads, only time — and another text or two — will tell.

If you'd told New Yorkers a year ago that President Trump and Mayor Zohran Mamdani would wind up regular texting companions, most would have raised an eyebrow — or simply laughed. Yet according to those orbiting the city’s power circles, that’s precisely what’s unfolded: not adversarial, often lighthearted, and thoroughly unexpected.Twice each week, sometimes more, messages pass between the Oval Office and City Hall. Their chatter, described as “cordial, even warm” by aides from both camps, vacillates between national headlines and the city’s perennial headaches. “They talk weather, sports, the UN, even the best bagel shops,” recalls one person close to the matter. No one’s pretending they’re best friends. But after years of frosty exchanges between the federal government and Gotham, this is a break from the script.Their relationship began back in November, behind closed doors, watched keenly by staffers expecting fireworks. The air, however, changed in an instant. President Trump, never one to shy from banter, greeted his counterpart with a grin and a quip: “You’re taller in real life — TV must have bad angles,” he joshed, provoking laughter rather than stand-offish posturing. Those initial moments, according to someone present, set a tone nobody saw coming.Over lunch, the banter continued. At one point, the mayor branded Trump a “fascist”— with a wry smile, sources say. The President responded with an amused pat on Mamdani’s jacket, sidestepping any hint of offense. Fast forward a few days, and a photo of Trump in an unexpectedly chic burgundy scarf — not dissimilar to one the mayor wore — circulated on social media. The city was quick to notice, and commentators archly asked if the President was taking fashion cues from his political opposite.Camaraderie, though, isn’t carte blanche. Serious divides crop up, as with the U.S. raid that led to Venezuelan leader Nicolás Maduro's arrest. Within hours, Mamdani picked up the phone to register disapproval. “I thought it was quick for him to be criticizing,” Trump would later tell a reporter, a touch of bewilderment in his retelling. “We get along, but I figured I’d get a month’s grace, at least.” Their rapport survives these barbs, perhaps because both sides keep sight of what’s at stake.Observers point to shrewd calculation as much as genuine warmth. One longtime city hall operator put it bluntly: “If you’re New York’s mayor and the White House holds purse strings, pragmatism beats grandstanding.” Federal dollars, after all, loom large over city budgets, and no mayor can afford to gamble away access—especially with Washington threatening to withhold funds from so-called “sanctuary cities,” a group in which New York firmly plants its flag.The dynamic extends to tricky policy disagreements. Trump, never subtle on social media, took a sledgehammer to congestion pricing plans, calling them an “unmitigated DISASTER” and demanding an immediate halt — claims at odds with first-wave data hinting at cleaner air and less traffic. That headline-grabbing rhetoric is complicated terrain for the mayor: he needs to defend the policy without weakening the relationship that keeps federal money — and influence — coming his way.Not everyone finds the arrangement strange. Andrew Kirtzman, a seasoned strategist and no stranger to city politics, notes that “Trump despised Bill de Blasio, wrote off much of the city for years. Suddenly, he appears to relish this new chapter. Mamdani must wake up surprised by it all.” Perhaps each man benefits: the President, recasting himself as engaged with his hometown after bruising local feuds; the Mayor, gaining a direct channel for advocacy and negotiation few predecessors ever enjoyed.On the ground and online, the mayor’s most vocal allies aren’t crying betrayal. Most see the unusual dialogue as smart politics, an exercise in maneuvering rather than capitulation. For now, transactional logic prevails. Neither side needs to advertise affection for the other; access, negotiation, and practical gain are enough.It has been a long time since New York City politics saw anything quite like this — a socialist mayor and a conservative president, keeping things civil and even, on odd occasions, lighthearted. The boundaries of ideology remain sharply drawn, but between the power centers of the city and the country, the communication lines have rarely been more open. Where this détente leads, only time — and another text or two — will tell.