You probably know him as the guy who spent years trolling his wife’s boss on Twitter. It was one of the strangest subplots in American political history. George T. Conway III, a high-powered conservative litigator, was married to Kellyanne Conway, the woman who arguably did more than anyone else to put Donald Trump in the White House. While she was inside the West Wing defending the President, George was on his phone, relentlessly dismantling the President's legal logic and mental fitness.
It was a mess. It was fascinating. And honestly, it was deeply weird for everyone watching.
But George Conway is more than just a "Twitter personality" or a disgruntled husband. He is a Yale Law graduate and a long-time member of the Federalist Society who spent decades building a reputation as a brilliant, if somewhat quiet, conservative legal mind. He wasn't some liberal activist who suddenly appeared out of nowhere. He was a true believer in the conservative movement who felt his party had lost its mind.
The Man Before the Tweets
George Conway didn't start out as a rebel. He was the quintessential establishment lawyer. After clerking for Judge Ralph K. Winter Jr. on the U.S. Court of Appeals for the Second Circuit, he joined Wachtell, Lipton, Rosen & Katz—one of the most prestigious and profitable law firms in the world. He made his bones there. He specialized in securities litigation, mergers and acquisitions, and constitutional law.
People forget that George Conway was a key player in the effort to impeach Bill Clinton. He was one of the "elves," the group of conservative lawyers who worked behind the scenes to help Paula Jones's legal team. He literally wrote the Supreme Court brief that argued a sitting president could be sued in civil court.
Think about that for a second.
The very legal precedent he helped create to go after Clinton would later be used against Trump. Life is funny that way. He spent his career arguing for a strict, some might say "originalist," interpretation of the law. He believed in the institutions. He believed in the rules.
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Then came 2016.
Initially, George was on board. He even considered a top job in the Trump administration, specifically heading the Civil Division of the Department of Justice. He eventually turned it down. Why? Because he saw the writing on the wall. He saw the firing of James Comey and the chaos of the early administration and decided he wanted no part of it.
That was the turning point.
The Lincoln Project and the Fracture of the Right
By 2019, George Conway wasn't just staying out of the administration; he was actively trying to take it down. He co-founded The Lincoln Project alongside other "Never Trump" Republicans like Steve Schmidt, Rick Wilson, and Reed Galen. The goal was simple but brutal: defeat Donald Trump at the ballot box and punish those who enabled him.
The Lincoln Project's ads were different. They weren't the standard, boring political spots you see during the local news. They were psychological warfare. They were designed to get under one person’s skin—Trump’s—and they worked.
George’s involvement was a massive blow to the administration’s credibility among suburban Republicans. If a guy who spent 30 years in the Federalist Society thought Trump was a threat to the Constitution, it gave other Republicans permission to feel the same way.
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But this came at a massive personal cost.
The public back-and-forth between George and Kellyanne was painful to witness. Trump called George a "husband from hell." Kellyanne defended her boss. George continued to post about the "narcissism" and "pathology" he saw in the Oval Office. It wasn't just a political disagreement; it was a fundamental clash of values played out on a global stage. Eventually, in 2023, the couple announced they were divorcing.
What George T. Conway III Gets Right (and Wrong)
If you listen to George speak now—whether it's on his podcast or his frequent appearances on CNN—he focuses heavily on the "psychological" aspect of politics. He’s obsessed with the DSM-5 (the diagnostic manual for mental disorders). He argues that you can't understand modern American politics through policy; you have to understand it through personality disorders.
The Legal Argument
George’s core argument is usually rooted in the law. He doesn't just say he dislikes a politician; he explains why their actions violate the Take Care Clause of the Constitution. He’s a "rules" guy in a world where the rules are being shredded.
- The 14th Amendment: He was one of the earliest and loudest voices arguing that the "insurrectionist clause" should disqualify Trump from the ballot.
- Executive Immunity: He has been a fierce critic of the idea that a President has absolute immunity for "official acts," calling it a legal absurdity.
- The Rule of Law: Basically, he believes no one is above the law, regardless of their title. Simple, right? Apparently not.
The Nuance of Disagreement
Not everyone on the left loves him, though. Progresses often point out that while George hates Trump, he still supports many of the conservative policies that paved the way for Trumpism. He’s still a fan of conservative judges (mostly). He still believes in small government. He’s an ally of convenience for the Democrats, not a convert to their cause.
Why He Still Matters in 2026
We are currently in a weird era of American history. The lines between entertainment, law, and politics have blurred into one giant, confusing mess. George Conway sits right at the intersection of that mess.
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He represents a specific type of American: the "homeless" conservative. These are people who haven't moved to the left, but who feel the right has moved so far toward populism and personality cults that they no longer recognize their own party.
Is he a hero? Or is he just a guy who saw the flame and decided to throw water on it?
It depends on who you ask. To his fans, he’s a truth-teller who sacrificed his marriage and his standing in the GOP to save the Republic. To his critics, he’s a traitor or a self-promoter who found a niche in being the "anti-Trump Republican."
Regardless of your opinion, his legal analysis is usually sharp. When he predicts how a court will rule, he’s often right—not because he has inside info, but because he understands how judges think. He knows the "vibe" of the legal establishment because he was a pillar of it for decades.
How to Follow the Work of George T. Conway III
If you want to actually understand his perspective beyond the 280-character snark, you have to look at his long-form writing and his legal commentary. He isn't just shouting into the void; he’s building a case.
Actionable Steps for the Informed Citizen
- Read the "Psychopath" Argument: Look up his 2019 essay in The Atlantic titled "Unfit for Office." It’s a dense, 11,000-word deep dive into the psychological fitness of a president. It’s the foundation for everything he’s said since.
- Listen to "George Conway Explains it All": This is his podcast with The Bulwark. It’s actually quite helpful for non-lawyers. He breaks down complex indictments and Supreme Court rulings into plain English.
- Check the Dissent: To get a full picture, read the responses to George from other Federalist Society members. The internal debate within the conservative legal world is actually much more interesting than the shouting matches on cable news.
- Follow the Court Filings: When a major constitutional case hits the docket, check if George has filed an amicus (friend of the court) brief. That’s where he does his most serious work.
George Conway is a reminder that politics isn't always about "Left vs. Right." Sometimes, it’s about "The System vs. The Individual." He chose the system. He chose the rules. He chose the Constitution, as he interprets it, over party loyalty. In a world of "yes men," having a "no man" who knows exactly where the bodies are buried is a very powerful thing indeed.
The story of George Conway isn't over. As long as there are legal battles over the limits of executive power, he’s going to be there, phone in hand, citing a case from 1803 to tell you why you’re wrong. It’s what he does. It’s who he is.