Some political leaders leave their mark through historic speeches or carefully crafted slogans. Donald Trump has always preferred a different approach: the well-aimed public attack. Sharp, direct, and impossible to ignore, his insults can be offensive or hilarious, polarizing or oddly entertaining, but they never fail to make headlines. Now, they've become a market.
Traders on Polymarket are currently speculating on who will be the next target of a Trump public insult before the June 30 deadline, making for one of the more colorful markets of the season.
How the Market Works
The rules are straightforward: any public statement by Trump that constitutes an insult, mockery, or personal attack against an individual qualifies for settlement. The target doesn't even need to be mentioned by name: context is enough, as long as it's reasonably clear who's in the crosshairs.
One case currently under review adds an unusual twist to the proceedings. An AI-generated image posted on Truth Social featured Marjorie Taylor Greene, Tucker Carlson, and Candace Owens, accompanied by the caption: "Get in loser, we're going losing."
Market analysts are still evaluating whether a meme with AI origins qualifies as an official insult under the resolution rules. It's the kind of question that probably didn't exist five years ago.
The Frontrunners
- Norah O'Donnell
The 60 Minutes correspondent may already have a head start… at least in terms of history.
During an April 26 interview, O'Donnell read aloud from the manifesto of Cole Allen, the shooter who breached the White House Correspondents' Dinner. Trump's response was immediate: "Well, I was waiting for you to read that because I knew you would because you're… horrible people."
He revisited the exchange weeks later in a May 14 interview with Sean Hannity, describing O'Donnell as "a very bad, you know, stupid reporter" and adding: "You could take anybody off the street, and it'd be as good as she is."
There's a catch, though: the market officially opened on May 26, so neither of those comments counts toward settlement. The real question is whether Trump will take another shot at O'Donnell before the end of June. Given the track record, traders seem to think the odds are reasonable.
- Jerome Powell
The former Federal Reserve Chair recently described the current political climate as a "stress test" for the central bank, the courts, and universities. That kind of public criticism rarely goes unnoticed by Trump, which is exactly why Powell has emerged as one of the stronger names on traders' radar.
- Jimmy Kimmel
Trump's friction with late-night television is practically a recurring storyline at this point. On June 1, he took to Truth Social to go after Stephen Colbert, labeling him "REALLY DUMB", and dropped a hint that other hosts might be next: "My score, for two weeks, is 38-0, with three more limping Late Night Talk Show Hosts, including Low Ratings Bill Maher and his Fake 'Laughing Machine,' to go."
Kimmel wasted no time firing back on his show: "I think Captain Cankleroo might be upset because our show won a Peabody Award on Sunday night."
With that kind of exchange already on the record, Kimmel remains one of the more likely names to watch heading into the final stretch of the month.
- Nicolás Maduro
The former Venezuelan president has been in Trump's orbit before, and recent events have put him back in the frame. During a trip to Beijing, Secretary of State Marco Rubio showed up wearing the exact same tracksuit Maduro had on when he was captured by U.S. forces in January, a visual jab that drew considerable attention and may be enough to prompt a fresh round of commentary from Trump.
The Bigger Picture
What makes this market genuinely entertaining isn't just the names involved, it's the near-certainty that something is coming. The only real variable is the target. With a few weeks still left on the clock, several rivalries already simmering, and everything going on the world right now, traders will need to keep one eye on the news, because with Trump, the next headline is rarely far away.
