Filipino American's public journey from conservative Republican to Democratic candidate for Congress

George Conway

The political metamorphosis of George Conway  from a lifelong conservative Republican to a Democratic congressional candidate has been driven primarily by his vehement opposition to Donald Trump.

On December 22, 2025, the man who once spent his days in the halls of the Federalist Society officially filed paperwork to run for Congress as a Democrat. He’s aiming for New York’s 12th District, looking to fill the shoes of the retiring Jerry Nadler in what is arguably the bluest slice of the Big Apple.

“I’m going into the arena. I’ve already put my money where my mouth is, but now it’s time to lay it all on the line,” Conway wrote in a social media post Monday before filing his papers.

Conway was a staunch Republican and a member of the right-wing Federalist Society for decades. His political journey isn’t just a political pivot; it’s a full-on leap across the aisle in a high-stakes battle for the nation’s soul. 

In the 1990s, he worked on conservative legal efforts including the lawsuit by Paula Jones against President Bill Clinton.

He initially supported Trump's 2016 campaign and was considered for several high-level Department of Justice positions, including Solicitor General. Conway turned them down, later describing the early Trump administration as a "sh*tshow in a dumpster fire." He began to see the administration not as a conservative movement, but as a "personality cult" that he could no longer support.

Personal toll

His political disagreements with his then-wife, Kellyanne Conway, who was serving as one of Trump's senior advisors, became more public. In 2018, Conway officially left the Republican Party, calling it a "personality cult." 

In her 2022 memoir Here’s the Deal, Kellyanne described George’s constant social media attacks on her boss as a betrayal of their marriage vows. She famously referred to his behavior as "cheating by tweeting."

The high-profile nature of the Conways' disagreement placed significant strain on their relationship. Trump himself frequently mocked the marriage, calling George a "whack job" and "husband from hell," which Kellyanne defended as him "punching back."

The couple's daughter, Claudia Conway, also publicly documented family tensions on TikTok, which added further media scrutiny to their private life. 

In August 2020, both George and Kellyanne announced they were stepping away from their professional roles (the Lincoln Project and the White House, respectively) to focus on their family, but observers noted the damage was already "too far gone." In 2023, the couple divorced.

Anti-Trump activism

 He co-founded The Lincoln Project in 2019 to persuade disaffected Republicans to vote against Trump. The project's social media advertisements are hard-hitting and most of all, they are highly irritable to Trump.

So, what exactly pushed a lifelong conservative to trade his GOP card for a Democratic primary ticket? It wasn't just one moment, but a series of "dumpster fire" realizations.

After initially being considered for top DOJ posts, Conway turned them down, later describing the early Trump administration as a "sh*tshow in a dumpster fire". He began to see the administration not as a conservative movement, but as a "personality cult" that he could no longer support.

A major trigger was the 2018 appointment of Matthew Whitaker as acting attorney general. Conway broke cover, co-authoring a New York Times op-ed arguing the move was unconstitutional. This led him to organize Checks and Balances, a group of conservative lawyers sounding the alarm on Trump's "betrayal of bedrock legal norms."

He became known for questioning Trump's mental fitness, later launching the Anti-Psychopath PAC in 2024 to highlight perceived dangers of a second Trump term.

By late 2024 and 2025, Conway’s alignment with Democratic causes became formal and total. In 2024, he donated nearly $930,000 to the Biden Victory Fund and actively campaigned for Kamala Harris.

Conway didn't just disagree with policy; he became convinced of Trump’s psychological unfitness. He co-founded The Lincoln Project to keep Trump from the White House and, in 2024, launched the Anti-Psychopath PAC to keep the spotlight on the perceived dangers of "Trumpism."

Running as a Democrat

Conway's Filipino heritage is through his mother, who was a chemist from the Philippines, while his father was an engineer; He grew up near Boston, attending Marlborough High School, graduating with honors from Harvard College (biochemistry), and earning his J.D. from Yale Law School, where he led the Federalist Society. 

He clerked for a federal judge, then joined the prestigious law firm Wachtell, Lipton, Rosen & Katz, becoming a partner by his mid-30s. 

Apparently, the event that made him decide to leave the sidelines and enter the political ring was his frustration with Senate Democrats who "caved" during government reopening negotiations in late 2025. Feeling the need for more "fearless" fighters in the arena, he decided to run himself, aiming to act as a legal "wingman" for Democrats like Jamie Raskin.

Conway is now entering a crowded primary field that includes names like Jack Schlossberg (JFK's grandson), but his message is clear: he’s gone from defending the conservative line to a "seasoned fighter" for democracy.

He describes himself as "going into the arena" to protect the rule of law and constitutional principles, which he believes the current Republican Party has abandoned.

“We need Democrats to take over Congress — and not just any Democrats, but the most fearless and relentless ones,” Conway wrote in social media prior to filing his candidacy. “The next two years will show us exactly how much lawlessness Republicans will accept. Doing nothing is the same as saying yes.”

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