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Nine years ago, George Conway was up front at Donald Trump’s election night party, wearing a “Make America Great” hat and embracing his then-wife, who was running the billionaire’s campaign. The tears of joy didn’t last long.

These days, the seasoned conservative lawyer and activist is determined to make Trump’s final two years in the White House a living hell. And he’s ready to do it as a Democrat.

Conway announced on Tuesday that he’s running for an open House seat representing Midtown Manhattan, joining an already crowded field that includes John F. Kennedy’s descendant, a survivor of the Parkland, Fla., school shooting, and a host of other formidable candidates vying for the seat held by Rep. Jerry Nadler, who was first elected to the House in 1993. Conway’s rollout, which has been the talk of Washington cocktail parties for months, comes on the five-year anniversary of the Jan. 6 insurrection at the Capitol, which sought to keep Trump in power after he lost the 2020 election.

Democrats across the country have launched campaigns for Congress vowing to fight Trump. Conway’s bid is different. His is almost entirely about Trump, to the point that the 62-year-old says he has no plans to stay in the job when he turns 67, suggesting he might serve just one term and leave Washington when Trump does. Even in his launch video, images of Trump appear from the start.

As one of the lawyers who set in motion the impeachment of President Bill Clinton and later pushed for Trump’s impeachments, Conway is positioning himself as a legal workhorse who could help Democrats finally hold Trump accountable—including during a potential third impeachment trial.

“We’re in a situation where we have a criminal President who violates his oath of office every day, defies the law, defies the Constitution, and basically thinks he’s above the law,” Conway tells TIME. “We need a Democratic Congress.”

To put it mildly, it’s been quite an evolution—and one that reflects the ongoing political conversation about what kind of politician might lead the nation through the Trump aftermath.

Conway used to run in the same circles as Ann Coulter and Matt Drudge, dated Laura Ingraham, and represented Paula Jones in her lawsuit against Clinton, which eventually became tied to the 42nd President’s impeachment. He lived in Trump Tower for years and recommended his then-wife, Kellyanne Conway, for the condo board. He was even seen as a top candidate to be the Trump Administration’s chief lawyer at the Supreme Court.

But after Trump’s election, Conway’s split from the GOP became clear, even as Kellyanne Conway served as Trump’s counselor with a prime second-floor West Wing office. George Conway left the Republican Party in 2018 and worked to defeat Trump in 2020 through a super PAC he founded, the Lincoln Project. He spent much of 2024 trying to help Vice President Kamala Harris win. (George and Kellyanne Conway announced their divorce in 2023.)

Now, Conway is a Democrat—“How could I be anything else now?” he asks—who says he would “absolutely” support Hakeem Jeffries’ bid to become Speaker in a Democratic House next year. “We have to do our first job, which is holding the President and his people accountable and making sure this never happens again,” Conway says.

Part of that, in Conway’s view, is what he’s calling “a second American reconstruction,” an overhaul of government safeguards “where we pass laws within the bounds of the Constitution to prevent this kind of authoritarian, autocratic corruption, this kind of threat to our system of government and way of life.” The reference to post-Civil War reforms isn’t accidental.

“I don’t need to do this. I’m a retired lawyer. I built my career. I made my money. I should be out skiing somewhere,” he laughs. But, he says, the risk is too great to trade his law license for a ski lift pass.

Democrats in New York’s 12th District have a built-in 33-point advantage, meaning the winner of the June 23 primary should easily win in November. The district is one of the wealthiest in the country and most Democratic in New York, but the primary is shaping up to be competitive. Jack Schlossberg, the 32-year-old author and Kennedy descendant, has garnered significant attention, as has 25-year-old Cameron Kasky, a Parkland survivor and gun safety activist. State Assemblymen Alex Bores, 34, Micah Lasher, 44, and journalist and lawyer Jami Floyd, 61, are also in the crowded primary. This primary is seen as one of the early signs of the story Democrats will tell voters ahead of midterm elections, which are widely expected to favor them.

But Conway is the candidate of the hour as he links his launch to the Jan. 6 anniversary. It’s definitely trolling, but it’s what earned him so many scathing tweets from Trump over the years. “I’ve been battling this guy for nearly a decade,” says Conway, who was called “Mr. Kellyanne Conway” in presidential tweets. “I know what makes him tick. I know how to fight these people. And this is going to require legal skills.”

First, though, it will require votes in a primary where only Democrats can vote. It must be noted that Democrats have to be convinced that Conway’s courage is enough to send him back to Washington.

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