One the country’s most well-known “Never Trump” former Republicans, George Conway, is running for Congress in a deep-blue Manhattan district, joining a crowded Democratic primary field of state and local lawmakers, activists, and even President Kennedy’s grandson. Mr. Conway was once married to President Trump’s 2016 campaign manager and top White House aide Kellyanne Conway. 

Mr. Conway started making a name for himself during the first Trump administration when he was posting on the website then-known as Twitter, taking jabs at the president. In 2019, during the first impeachment investigation of Mr. Trump, Mr. Conway went on television to declare that he was mentally “unfit” to serve as commander-in-chief. He referenced the DSM-5 — the gold-standard guide for diagnosing mental disorders — to justify his claim. 

He and his ex-wife divorced in 2023, years after his attacks on Mr. Trump began. Since 2019, he has been a mainstay on liberal outlets like the cable news channel formerly known as MSNBC, a number of podcasts, and most recently as a contributor for The Bulwark, a successful online publication. 

On Monday, Mr. Conway filed to run in New York’s 12th congressional district, which sits entirely on the island of Manhattan. It stretches from Morningside Heights to Chelsea and between the East and Hudson Rivers. 

It is currently represented by Congressman Jerry Nadler, who is retiring in 2026. The seat is the most Democratic in New York State, with Vice President Kamala Harris having received more than 80 percent of the vote there in 2024. 

Mr. Conway filed his Federal Election Commission paperwork to run for Congress on Monday afternoon. His campaign did not immediately respond to a request for comment. 

He most recently made headlines for being seen outside of his neighbor John Bolton’s home at Bethesda, Maryland. Mr. Bolton has been charged with improperly handling classified information in connection with his tell-all book about his time as Mr. Trump’s national security advisor during his first term. 

Mr. Conway’s shift to a fierce critic of the Republican Party and Mr. Trump himself would likely seem shocking to the young conservative attorney he once was. In the 1990s, he represented Paula Jones in her civil litigation against President Clinton, who had been accused of sexual harassment. Mr. Conway later became one of the first individuals to hear the audio recordings of Linda Tripp’s conversations with Monica Lewinsky — information which would later lead to Mr. Clinton’s impeachment. 

Mr. Conway is now the eleventh Democrat to throw their hat into the ring to succeed Mr. Nadley, with a bevy of other candidates trying to carve out a lane in what could be one of the most crowded primaries of 2026. 

The most notable candidates so far include state assemblyman Micah Lasher, a protégé of Mr. Nadler; assemblyman Alex Bores; Parkland school shooting survivor and Democratic activist Cameron Kasky; and the Kennedy scion, Jack Schlossberg. 

With a field that large, it is entirely possible that a candidate could win the Democratic primary with somewhere around 20 percent of the vote, given that New York does not have ranked-choice voting or a runoff election system for their primaries. 

The most recent example of such an event was in 2022, when Congressman Dan Goldman won his seat with only one-quarter of all votes cast, defeating his nearest opponent by two points.