George Conway looked directly into a camera, pointed at the U.S. Capitol, and told Donald Trump he's going to put him in an orange jumpsuit. This was a campaign ad, not a fever dream. Conway is running for Congress in Manhattan, and apparently subtlety is not part of the platform.
The Ad That Made No Attempt at Diplomacy
Conway dropped a 60-second spot on Monday that opens with him reminding Trump, personally, that he cost him "88 f------ million dollars" and has "only just gotten started." The ad was filmed overlooking the Capitol. The message was not ambiguous.
According to Fox News, Conway promised that Trump's name would ultimately appear on exactly one thing when he's done: "the orange jumpsuit you're going to have to wear in prison." He then pointed at the Capitol and pledged to hold Trump's "third and final impeachment trial" there, adding that he'd "enjoy every minute of that."
The ad does not specify what conduct Conway believes would justify impeachment. His campaign did not respond to Fox News when asked for clarification. Sometimes the vibe is the whole platform.
Who Is This Guy, Exactly
If you missed the first Trump term, here's the short version. George Conway spent four years as one of the most visible and relentless conservative critics of Donald Trump, doing it largely while his then-wife Kellyanne Conway served as one of Trump's closest advisors and campaign managers. The couple divorced in 2023 after more than two decades of marriage.
Conway co-founded the Lincoln Project, the anti-Trump political operation that raised and spent enormous sums attacking the president during the 2020 cycle. He became a near-permanent fixture on cable news throughout Trump's first term, a lawyer who clearly knew how to give a quote and was never going to run out of material.
Now he's a Democratic candidate running in New York's 12th Congressional District, which covers a chunk of central Manhattan and is about as blue a district as American electoral maps produce. The seat opened up because longtime Rep. Jerrold Nadler is retiring, and approximately everyone in New York with a Twitter account and a grudge decided to run for it.
The Race He's Actually In
Here's the part where we have to deliver some reality to Conway's very cinematic campaign. He is losing. According to an Emerson College poll released in May, Conway sits at 10% support among likely Democratic primary voters. State Assembly members Micah Lasher and Alex Bores are leading at 22% and 20% respectively. Jack Schlossberg, the JFK grandson who has turned himself into something of a social media personality, is at 11%.
Lasher has a formidable endorsement stack. Fox News reports he's backed by retiring Rep. Nadler himself, Governor Kathy Hochul, and former New York City Mayor Mike Bloomberg. That is not a lineup you beat with a punchy ad and some extremely personal beef with the former president.
The primary is June 23. Whoever wins will almost certainly win the general election given the district's overwhelming Democratic registration advantage. So this race is basically the whole ballgame, and right now Conway is watching it from fourth place.
The Impeachment Question Nobody Asked Democratic Leadership
Conway's impeachment pledge lands in an interesting place politically because, as Fox News points out, Democratic leadership has not actually signed on to pursuing a third impeachment even if the party takes back the House in November. A number of individual Democratic lawmakers have called for Trump's removal, but the caucus as a whole has not committed to another round.
Trump was impeached twice during his first term. The House voted to impeach him in January 2020 over the Ukraine pressure campaign, and the Republican-controlled Senate acquitted him. Then the House impeached him again in January 2021 following the Capitol attack, and the Senate acquitted him a second time. Two impeachments, two acquittals, one guy who is now serving a second term anyway.
So when Conway promises a third impeachment that will "put him away for good," he's making two assumptions that do not currently have much support: that Democrats will retake the House, and that the caucus will immediately pursue impeachment rather than, say, investigating or legislating or doing literally any of the other things a congressional majority can do.
The Part That Is Genuinely Funny
Look, you have to give Conway some credit for the sheer audacity of the pitch. He moved from Bethesda, Maryland to Manhattan to run for a seat he's currently losing in a primary where he doesn't have the backing of the governor, the retiring incumbent, or a former mayor. His main qualification, as presented to voters, appears to be that he hates Donald Trump more than anyone else on the ballot and is willing to say so in the most theatrical terms possible.
That's a choice. It's a very specific product for a very specific consumer. In a district full of progressive Manhattan voters who would probably enjoy watching someone personally antagonize the president from the floor of Congress, it's not the worst pitch in the world. It's just apparently not enough of a pitch to crack the top three in the polls three weeks out from the primary.
The Dingo Take
There is something almost poignant about George Conway's entire political arc, if you squint at it the right way. He spent years in a household that was essentially a living metaphor for the entire country's relationship with Trump, one half deeply embedded in the project and one half publicly losing his mind over it. Now he's running for Congress on a platform that is basically pure, distilled personal grievance dressed up in constitutional language. It's very American.
The problem isn't the anger. The anger is legitimate. Trump has spent the better part of a decade demonstrating that American institutions will absorb almost unlimited punishment without consequences for the person throwing the punches, and the frustration Conway is performing in that ad is something a lot of people feel at a molecular level. The problem is that promising a third impeachment of a guy who skated on two previous ones, without specifying what he did wrong this time or how the Senate arithmetic has changed, is more cathartic theater than actual political strategy.
Conway is currently in fourth place with a week and a half to go, running behind a JFK grandson who became famous for posting videos online. That's not a knock on Schlossberg, who by all accounts has run a serious campaign. It's just a data point. Personal feuds make for excellent television. They are a somewhat shakier foundation for a congressional career. If Conway wants to put Trump in an orange jumpsuit, he is going to need to figure out how to get more than 10% of Manhattan Democrats to vote for him first.
