Trump Depicts Kimmel, Fallon and Colbert as Panhandlers…

On July 25, 2026, Donald Trump shared a series of AI-generated images on Truth Social targeting several political and celebrity adversaries. Among these posts was a cartoon depicting late-night hosts Jimmy Kimmel, Jimmy Fallon, and Stephen Colbert sitting on a New York City sidewalk, portrayed as panhandlers holding signs that claimed they were talentless and in need of money.

What happened

The AI-generated image served as a visual extension of remarks Trump made during his speech at the White House Correspondents’ Association Dinner. During that event, Trump criticized the association's decision not to hire a comedian, specifically naming Kimmel, Fallon, and Colbert as individuals he deemed terrible, talentless, and angry. The digital illustration featured the hosts seated on a sidewalk with cardboard signs reading, “Talentless Not Funny Ex Comedians Need Money,” while the wall behind them displayed the text “Late Night Is Over.”

This post was part of a rapid succession of over a dozen AI-altered or AI-generated images shared by Trump on a Sunday. Other targets of these digital attacks included former New Jersey governor Chris Christie, Rosie O’Donnell, and Bruce Springsteen. The incident follows a pattern of digital antagonism from the president toward these media figures. Notably, earlier in 2026, following Stephen Colbert’s final broadcast, Trump shared an AI-generated video that depicted him throwing the host into a dumpster, accompanied by written insults regarding the host's talent and career.