Welcome back to The Red Letter.
George Conway doesn’t think impeachment failed—he thinks Congress did.
When I caught up with Conway—after a few tech hiccups getting him onto Substack Live—he was calling in from his girlfriend’s Central Park West apartment, casually toggling between locations in Manhattan as he launches his unlikely bid for Congress in New York’s 12th Congressional district. But there was nothing casual about his message.
Conway, the longtime conservative lawyer turned anti-Trump crusader, is now running as a Democrat in New York and he’s making a blunt case: not only should President Donald Trump be impeached again, but this time, it could actually work.
“We don’t have a choice,” he told me. “I don’t see…how we can last 34 more months of this.”
That’s a striking argument coming from someone who has spent years watching impeachment fail to remove Trump from office. But Conway insists the problem wasn’t the mechanism, it was how it was executed.
The next time, he says, should look very different.
Instead of what he describes as “show arguments” and political speeches, Conway envisions something closer to an actual courtroom trial: live witnesses, cross-examination, and a sustained effort to expose contradictions in real time.
“A real trial,” he said. One that forces answers and makes it impossible for officials to dodge questions the way they do in five-minute congressional hearings designed more for viral clips than accountability.
It’s the kind of argument you’d expect from a litigator. And Conway is explicit about it: Congress, he says, needs to start behaving less like a cable news panel and more like a courtroom.
That mindset also shapes how he’s thinking about one of the issues I’ve been reporting on closely: the Epstein case.
When I asked him about the confusion surrounding settlements and testimony from Epstein’s longtime lawyers Richard Kahn and Darren Indyke, Conway didn’t speculate but he zeroed in on something more important: documentation.
“If you’re paying somebody in a settlement, it’s got to be documented,” he said. “There’d have to be a paper trail.”
For Conway, that’s the throughline—not just in Epstein, but in what he sees as a broader pattern of misconduct across the Trump era. The answers, he believes, already exist. They’re just buried in documents Congress hasn’t fully pursued.
And if he’s elected, he says, he intends to go after them.
“Absolutely,” he said when I asked whether he would continue investigating Epstein-related issues in Congress. But he quickly broadened the scope: the Justice Department’s handling of evidence, internal communications, decisions around Ghislaine Maxwell—all of it, in his view, demands scrutiny.
“This is the most corrupt administration in American history,” he said, before rattling off a list of controversies that, in his telling, only scratch the surface.
Still, Conway’s campaign isn’t just about Trump. It’s also about something more personal: reinvention.
After decades tied to the conservative legal movement—and a high-profile role in the Clinton-era battles—Conway formally became a Democrat in December. It’s a shift that raises obvious questions for voters, and he doesn’t shy away from them.
Trump, he says, forced a kind of reckoning.
“You kind of develop your identity when you’re young,” he told me. “But when you step back, which Trumpism forced me to do, to think about ‘well what are my values? What do I believe in’ The rule of law and ask what you actually believe—the rule of law. I do believe in limited government because I was always fearful of … a powerful government could be abused by bad people.”
In fact, Conway argues something that would have been unthinkable a decade ago: that today’s Democratic Party is, in many ways, the true home of conservative principles.
“The modern conservatives, frankly, are Democrats,” he said.
That argument may resonate with a certain slice of voters. But Conway isn’t running in a vacuum.
🔐 He’s also running against a Kennedy—and what he told me about that race reveals where the Democratic Party may be heading next.
