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Nine years ago, George Conway was down front at Donald Trump’s election night party, festooned in a Make America Great hat and embracing his then-wife, who ran the billionaire’s campaign. The tears of joy would not last long.

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

Conway on Tuesday announced that he is running for an open House seat representing Midtown Manhattan, joining an already crowded field that includes John F. Kennedy’s lone grandson, a survivor of the Parkland, Fla., school shooting, and a raft of other formidable candidates looking to fill a seat represented by Rep. Jerry Nadler, who first was elected to the House in 1993. Conway’s rollout—which has been the subject of Washington cocktail party chatter for months—comes on the five-year anniversary of the Jan. 6 insurrection at the Capitol that 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 of being in the job when he turns 67, suggesting he may serve just one term and leave Washington when Trump does. Even in his launch video, images of Trump are there from the start.

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

“We are in a situation where we have a criminal President who abrogates his oath of office every day, defies the law, defies the Constitution, and frankly thinks he's the law,” Conway tells TIME. “We need a Democratic Congress.”

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It has been, to undersell it, quite the evolution—and one that nods to the ongoing conversation in politics about just what mold of politician might lead this nation through the Trump hangover. 

Conway used to run in the same circles as Ann Coulter and Matt Drudge, dated Laura Ingraham, and represented Paula Jones in her case against Clinton that eventually got entangled with 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 leading to be the Trump Administration’s main lawyer at the Supreme Court.