How a lifelong conservative thinks he can reinvent himself as a New York Democrat—and why voters should be forgiven for laughing.
You have got to be kidding me.
George Conway—yes, that George Conway, the conservative lawyer who spent decades building his career in Republican legal circles before discovering that dunking on Donald Trump on Twitter could make him a cable news darling—now wants us to believe he’s the Democratic savior New York’s 12th Congressional District has been waiting for.
Let me get this straight: A man who admits that his party switch ‘could confuse some voters and ‘put some people off’ thinks the solution to Democratic woes is… himself? A recently minted Democrat whose entire political identity for the past forty-some years was wrapped up in conservative Federalist Society legal philosophy?
The sheer audacity is almost admirable. Almost.
Conway’s pitch, delivered to paid members of the liberal media outlet Democracy Docket, reads like a political Mad Lib written by someone who just discovered MSNBC exists. “This is the time for a lawyer who has never been in politics to go into politics,” he declared, apparently unaware that “I have no political experience” stopped being a compelling argument somewhere around January 2021.
But wait, there’s more! Conway wants to serve as a “wingman” to other attorneys in politics, like Maryland Democratic Rep. Jamie Raskin and New York Democratic Rep. Dan Goldman. A “wingman.” As if what Congress desperately needs is another lawyer providing air support to the lawyers already there. Never mind that Goldman himself is a freshman representative still finding his footing, or that “career prosecutor turned congressman” is practically a genre at this point.
Just The News: Trump critic George Conway considering campaign for Nadler’s seat as a Democrat
Conway, who divorced his wife and former Trump adviser Kellyanne Conway in 2023, told donors at a private virtual event for paid members of the liberal media outlet Democracy Docket on Tuesday that he was inspired to consider a campaign after eight Senate Democrats voted to reopen the government without a deal to extend expiring health care subsidies.
The former conservative said he would run as a Democrat if he jumped into the race, but admitted that the party swap could confuse some voters and “put some people off.”
“This is the time for a lawyer who has never been in politics to go into politics,” Conway said. “We need to do things to make sure there is accountability. We need to undo the damage that he has done to the Justice Department. And then we have to create new safeguards that are going to make the Watergate safeguards look like child’s play.”
Let’s talk about Conway’s chances, shall we?
The Math Doesn’t Math
Conway would join a crowded field of 10 Democratic candidates, including one of Nadler’s allies and a democratic socialist. In a district that skews heavily progressive, Conway brings to the table: a lifetime of conservative legal advocacy, a famous divorce from a Trump aide, and a really active Twitter account.
That’s it. That’s the resume.
He has no political organization. No constituent services record. No history of community organizing in the district. No deep relationships with New York Democratic power brokers who might smooth his path. What he does have is name recognition—but here’s the thing about name recognition: it cuts both ways.
The Identity Crisis
New York Democratic primary voters are generally not looking for converts from conservatism who have changed their minds because they dislike a particular Republican. They’re looking for candidates with a demonstrated commitment to progressive values, health care expansion, workers’ rights, climate action—you know, the issues that actually affect people’s lives.
Conway’s Road to Damascus moment apparently came when Trump fired former FBI Director James Comey. That’s his origin story. Not economic injustice. Not civil rights. Not any policy disagreement whatsoever—just one personnel decision that offended his sense of institutional propriety.
And now he’s mad that eight Senate Democrats voted to reopen the government without a deal to extend expiring health care subsidies. So his response to Democrats not being Democrat enough is… to run as a Democrat himself? After being a Republican for his entire adult life?
The cognitive dissonance is deafening.
The Trust Gap
Why, exactly, should Democratic voters trust that Conway’s conversion is genuine and not just opportunistic? He supported Trump when he won in 2016—so we know his judgment was questionable at best when it mattered most. His entire public profile is built on being the “good” conservative, the one who’ll come on liberal shows and say what Democrats want to hear about Trump while maintaining his conservative bona fides on virtually everything else.
That might play well in green rooms at CNN. It’s not going to play well in a Democratic primary in Manhattan, where voters have actual progressives to choose from.
The Reality Check
Here’s what Conway seems to misunderstand: Being against Trump is not a political platform. It’s not a qualification. It’s barely even notable in a Democratic primary in New York City, where being anti-Trump is about as distinctive as enjoying pizza.
And let’s not forget Conway’s recent political judgment. He was a co-founder of The Lincoln Project, the anti-Trump super PAC that became a progressive darling—right up until it imploded in scandal. Remember that? The organization faced serious allegations about its handling of misconduct by co-founder John Weaver, questions about where donor money actually went, and accusations that its leaders were profiting handsomely while claiming to save democracy. Conway eventually distanced himself from the group, but not before the stench of dysfunction and grift had already settled in.
So when Conway asks Democratic primary voters to trust his judgment and his commitment to accountability, they might reasonably wonder: Where was that commitment when your own organization was melting down? Where was the lawyer’s due diligence then?
Congressional races are won by candidates who understand their districts, who’ve put in the groundwork, who can articulate a vision beyond “I’m a lawyer who’s good at Twitter and I promise I’m a Democrat now, trust me.” They’re won by people who don’t have to explain away decades of opposing the very policies their new party stands for—or their involvement in a political grift operation that left many Democrats feeling used and manipulated.
Could Conway win? In the sense that anything is technically possible, sure. Lightning could strike. The other ten candidates could simultaneously combust. Democratic primary voters could collectively decide that what they really want is a political neophyte whose claim to fame is a messy public divorce, a vendetta against his ex-wife’s former boss, and association with one of the most embarrassing political organizations of the Trump era.
But should you bet your mortgage on it? Only if you enjoy living in a cardboard box.
George Conway’s congressional aspirations aren’t just unlikely—they’re a masterclass in main character syndrome. He’s spent so much time being celebrated in certain circles for saying obvious things about Trump that he’s apparently convinced himself he’s the hero of this story.
He’s not. He’s the punchline.
And Democratic primary voters in New York’s 12th District, faced with serious candidates who’ve actually done the work, are going to deliver that punchline with extreme prejudice.
You have to be kidding me, indeed.