Shock Alliance: NYC’s Left-Wing Mayor Finds Common Ground With Trump

Paul Riverbank, 1/14/2026NYC's progressive mayor and Trump forge an unlikely, pragmatic alliance—texting, debating, getting things done.

Looking back on that day, it’s clear their conversation was just opening act. What most missed was the almost casual exchange of phone numbers—a move hardly worth a headline by itself, yet it’s since turned into a relationship that has city insiders and longtime observers scratching their heads.

Few would peg these two as texting buddies, yet aides now confirm that, like clockwork, Mamdani and Trump exchange messages two, sometimes three times a week. Topics swing from Venezuela’s tangled crisis, with Trump’s decision to oust Nicolás Maduro still drawing sharp lines, to the more local—say, the intricacies of affordable housing tweaks or a dispute over a Fifth Avenue shoveling regulation. By all accounts, the tone is far from chilly. “Surprisingly conversational” is the phrase I heard from one staffer.

The differences between them haven’t exactly vanished. Early this spring, Trump ordered a swift military action against Maduro’s regime—and Mamdani didn’t just criticize the move in carefully worded press releases. He picked up the phone within the hour, calling the president to spell out, unvarnished, his objections: “an act of war and a violation of international law,” he later repeated in public. The president, in his own style, seemed almost amused, telling the press, “He certainly doesn’t wait to criticize. I thought there’d be a bit of a honeymoon, at least until Christmas.”

Yet for all their public posturing, the lines are never closed. When I asked a former aide what they’d make of this unusual backchannel, the response was blunt: “Look, there’s too much at stake—infrastructure money, disaster relief, even police funding. No one can afford a shouting match right now, not in public or in texts.” Behind the pragmatism lurks the reality: for Mamdani, who campaigned on radical change, a working relationship with Washington isn’t a luxury, it’s a necessity.

It’s not lost on observers that Trump, so famously antagonistic toward former mayor Bill de Blasio, has been uncharacteristically at ease with Mamdani, who constitutes an even more progressive challenge. “It’s a striking turn,” says Andrew Kirtzman, who’s spent decades charting New York’s political undercurrents. “Trump genuinely hated de Blasio—there was no rapport, not even civility. With Mamdani, the president jokes, asks about his family. They’ve found some strange wavelength.” Mamdani himself has admitted, to those who ask, that the entire experience still borders on surreal.

For the city’s left, this camaraderie triggers the odd concern: Does cozying up risk eroding Mamdani’s base? So far, the grassroots have mostly shrugged, rationalizing that their mayor is in the room to win change, not accolades. “Transactional, that’s what this is,” Kirtzman notes. “It’s the only way it works for both men.”

Compare this moment to what came before. Eric Adams, painted as the ‘Trump-friendly’ mayor, never managed direct outreach—everything filtered through layers, intermediaries, half-hour waits. By contrast, the new mayor bypasses all that, relying on speed-dial and candid notes straight from phone to phone.

It would be easy to mistake this relationship for a budding détente, but that misses the point. Both have an acute sense of political self-preservation; both know that, in a city this big and a federal government this vast, progress demands flexibility. Whether the issue is funding for subway fixes or navigating the next foreign policy crisis, the unofficial policy seems to be: talk first, argue later.

The public, for the most part, is watching with curiosity, perhaps even a touch of relief. In place of headline-grabbing brawls, there’s gritty governance and compromise—at least for now. Only time will tell if this experiment in direct diplomacy can hold when the next flashpoint arrives. For the moment, it’s a study in political realism, writ large and personal, carried out one unexpected text message at a time.

When Mayor Zohran Mamdani strode into the White House last November, anticipation buzzed in the room—no one was quite sure what to expect. An awkward handshake? Maybe a heated exchange, given the political gulf. Yet as the doors closed, those inside caught the unlikely sight: President Trump and the famously left-wing New York City mayor swapping jokes like old debate rivals, a far cry from the fireworks many had braced for.Looking back on that day, it’s clear their conversation was just opening act. What most missed was the almost casual exchange of phone numbers—a move hardly worth a headline by itself, yet it’s since turned into a relationship that has city insiders and longtime observers scratching their heads.Few would peg these two as texting buddies, yet aides now confirm that, like clockwork, Mamdani and Trump exchange messages two, sometimes three times a week. Topics swing from Venezuela’s tangled crisis, with Trump’s decision to oust Nicolás Maduro still drawing sharp lines, to the more local—say, the intricacies of affordable housing tweaks or a dispute over a Fifth Avenue shoveling regulation. By all accounts, the tone is far from chilly. “Surprisingly conversational” is the phrase I heard from one staffer.The differences between them haven’t exactly vanished. Early this spring, Trump ordered a swift military action against Maduro’s regime—and Mamdani didn’t just criticize the move in carefully worded press releases. He picked up the phone within the hour, calling the president to spell out, unvarnished, his objections: “an act of war and a violation of international law,” he later repeated in public. The president, in his own style, seemed almost amused, telling the press, “He certainly doesn’t wait to criticize. I thought there’d be a bit of a honeymoon, at least until Christmas.”Yet for all their public posturing, the lines are never closed. When I asked a former aide what they’d make of this unusual backchannel, the response was blunt: “Look, there’s too much at stake—infrastructure money, disaster relief, even police funding. No one can afford a shouting match right now, not in public or in texts.” Behind the pragmatism lurks the reality: for Mamdani, who campaigned on radical change, a working relationship with Washington isn’t a luxury, it’s a necessity.It’s not lost on observers that Trump, so famously antagonistic toward former mayor Bill de Blasio, has been uncharacteristically at ease with Mamdani, who constitutes an even more progressive challenge. “It’s a striking turn,” says Andrew Kirtzman, who’s spent decades charting New York’s political undercurrents. “Trump genuinely hated de Blasio—there was no rapport, not even civility. With Mamdani, the president jokes, asks about his family. They’ve found some strange wavelength.” Mamdani himself has admitted, to those who ask, that the entire experience still borders on surreal.For the city’s left, this camaraderie triggers the odd concern: Does cozying up risk eroding Mamdani’s base? So far, the grassroots have mostly shrugged, rationalizing that their mayor is in the room to win change, not accolades. “Transactional, that’s what this is,” Kirtzman notes. “It’s the only way it works for both men.”Compare this moment to what came before. Eric Adams, painted as the ‘Trump-friendly’ mayor, never managed direct outreach—everything filtered through layers, intermediaries, half-hour waits. By contrast, the new mayor bypasses all that, relying on speed-dial and candid notes straight from phone to phone.It would be easy to mistake this relationship for a budding détente, but that misses the point. Both have an acute sense of political self-preservation; both know that, in a city this big and a federal government this vast, progress demands flexibility. Whether the issue is funding for subway fixes or navigating the next foreign policy crisis, the unofficial policy seems to be: talk first, argue later.The public, for the most part, is watching with curiosity, perhaps even a touch of relief. In place of headline-grabbing brawls, there’s gritty governance and compromise—at least for now. Only time will tell if this experiment in direct diplomacy can hold when the next flashpoint arrives. For the moment, it’s a study in political realism, writ large and personal, carried out one unexpected text message at a time.