George Conway Crosses the Aisle—Shakes Up Manhattan Dems’ Turf War

Paul Riverbank, 12/23/2025 George Conway, a prominent Trump critic and former GOP legal insider, eyes New York’s 12th District seat, injecting political drama and cross-party intrigue into a crowded Manhattan race. His bid could challenge party loyalties and redefine the district’s appetite for transformation.

The field in the 12th was already a parade of distinct personalities: Jack Schlossberg bringing the echo of Camelot, gun safety advocate Cameron Kasky showing up with the scars and certainty of youth, and veteran state officials like Alex Bores and Micah Lasher working their own turf. Not to be overlooked, Alan Pardee, with his Wall Street credentials, and Jami Floyd, a familiar face for anyone who remembers her time as a White House fellow in the Clinton years. Up until Conway stepped in, insiders knew the contest would be crowded, but few predicted just how much gravity his candidacy might possess.

For Conway, this turn isn’t exactly a clean break from his past—it’s more like an uneasy evolution. His career arc bounces between opposing chapters: crucial player in Paula Jones’s legal team, potential Trump administration appointee (which never materialized), and, eventually, a very public dissenter from Trumpism. His marriage to Kellyanne Conway—who herself helped steer the country through four chaotic years as one of Trump’s closest advisers—made for the kind of front-page drama most political families only imagine. That relationship, punctuated by the couple’s very public differences, officially ended last year.

And then, there’s the Conway name itself, now a bit of a Rorschach test depending on which cable channel you favor. His regular MSNBC and CNN appearances, often winding and almost always hyper-articulate, have built him a reputation as a fierce debater willing to challenge orthodoxy—Republican or Democratic. Claudia Conway, his daughter, managed to generate her own buzz in totally different circles: first through TikTok battles over the Trump presidency, then as an “American Idol” contestant, reminding New Yorkers that politics and pop culture rarely travel parallel paths here.

The timing of George Conway’s paperwork prompted at least one notable local to rethink things. On the very same day, City Council member Erik Bottcher announced he was dropping his congressional ambitions and would run instead for the state senate. A coincidence? Maybe. Or maybe just proof that, in New York politics, the script never matches the stage directions.

Don’t misunderstand—filing with the FEC isn’t equivalent to jumping in feet first. But for a man who once joked on a podcast about embarking on “either the stupidest thing I’ve ever done, or the best thing,” it’s a pretty good sign he means business. Behind the scenes, he’s also taken practical steps—hiring a Democratic pollster, kicking off those internal conversations that precede every high-stakes campaign. These details matter, particularly in a district where “Democrat” is non-negotiable on the ballot, but political identity is perpetually in flux.

What exactly are New York’s 12th District voters looking for this time around? That’s more complicated than party allegiance. Some will surely be drawn to Conway’s legal expertise, his years spent navigating the sharp end of America’s political divide. Others may bristle at his recent jumps across the ideological spectrum or wonder if his prominence on television will translate to gritty constituent work. History offers few guarantees, and New Yorkers, for all their urbanity, tend to be allergic to inauthenticity.

Yet at a moment when the city, and the country, sense realignment in the air, Conway’s bid—still unofficial, but now impossible to ignore—practically begs the question. Can a candidate known for bucking both his party and his personal relationships persuade Manhattan liberals he’s the right man to represent them? Or will the 12th become the next proving ground for new faces, old family names, and the never-ending shuffle that is New York politics?

Expect clarity after the holidays, Conway says—or at least more news. But for now, his entrance serves as a reminder: in the nation’s most watched districts, unpredictability isn’t just tolerated. It’s practically required.

If you happened to pass through Manhattan’s 12th Congressional District this week, you might've felt the political weather shift ever so slightly. George Conway—who, until fairly recently, could be counted among the stalwarts of conservative legal circles—has gone from commentator to possible contender. He’s filed paperwork with the FEC, turning whispers into something concrete: a bid for the U.S. House seat about to be vacated by Jerry Nadler after a long, storied run. A routine move, perhaps, on paper—but in reality, it’s more like dropping a boulder into a crowded pond.The field in the 12th was already a parade of distinct personalities: Jack Schlossberg bringing the echo of Camelot, gun safety advocate Cameron Kasky showing up with the scars and certainty of youth, and veteran state officials like Alex Bores and Micah Lasher working their own turf. Not to be overlooked, Alan Pardee, with his Wall Street credentials, and Jami Floyd, a familiar face for anyone who remembers her time as a White House fellow in the Clinton years. Up until Conway stepped in, insiders knew the contest would be crowded, but few predicted just how much gravity his candidacy might possess.For Conway, this turn isn’t exactly a clean break from his past—it’s more like an uneasy evolution. His career arc bounces between opposing chapters: crucial player in Paula Jones’s legal team, potential Trump administration appointee (which never materialized), and, eventually, a very public dissenter from Trumpism. His marriage to Kellyanne Conway—who herself helped steer the country through four chaotic years as one of Trump’s closest advisers—made for the kind of front-page drama most political families only imagine. That relationship, punctuated by the couple’s very public differences, officially ended last year.And then, there’s the Conway name itself, now a bit of a Rorschach test depending on which cable channel you favor. His regular MSNBC and CNN appearances, often winding and almost always hyper-articulate, have built him a reputation as a fierce debater willing to challenge orthodoxy—Republican or Democratic. Claudia Conway, his daughter, managed to generate her own buzz in totally different circles: first through TikTok battles over the Trump presidency, then as an “American Idol” contestant, reminding New Yorkers that politics and pop culture rarely travel parallel paths here.The timing of George Conway’s paperwork prompted at least one notable local to rethink things. On the very same day, City Council member Erik Bottcher announced he was dropping his congressional ambitions and would run instead for the state senate. A coincidence? Maybe. Or maybe just proof that, in New York politics, the script never matches the stage directions.Don’t misunderstand—filing with the FEC isn’t equivalent to jumping in feet first. But for a man who once joked on a podcast about embarking on “either the stupidest thing I’ve ever done, or the best thing,” it’s a pretty good sign he means business. Behind the scenes, he’s also taken practical steps—hiring a Democratic pollster, kicking off those internal conversations that precede every high-stakes campaign. These details matter, particularly in a district where “Democrat” is non-negotiable on the ballot, but political identity is perpetually in flux.What exactly are New York’s 12th District voters looking for this time around? That’s more complicated than party allegiance. Some will surely be drawn to Conway’s legal expertise, his years spent navigating the sharp end of America’s political divide. Others may bristle at his recent jumps across the ideological spectrum or wonder if his prominence on television will translate to gritty constituent work. History offers few guarantees, and New Yorkers, for all their urbanity, tend to be allergic to inauthenticity.Yet at a moment when the city, and the country, sense realignment in the air, Conway’s bid—still unofficial, but now impossible to ignore—practically begs the question. Can a candidate known for bucking both his party and his personal relationships persuade Manhattan liberals he’s the right man to represent them? Or will the 12th become the next proving ground for new faces, old family names, and the never-ending shuffle that is New York politics?Expect clarity after the holidays, Conway says—or at least more news. But for now, his entrance serves as a reminder: in the nation’s most watched districts, unpredictability isn’t just tolerated. It’s practically required.