President Donald Trump shared a series of AI-generated images on Truth Social, mocking longtime critics and political foes, including CNN anchor Kaitlan Collins, entertainer Rosie O’Donnell, late-night hosts Stephen Colbert, Jimmy Kimmel and Jimmy Fallon, former New Jersey Gov. Chris Christie, musician Bruce Springsteen and Iranian officials.
The spree began with an AI-generated image placing Collins’ face on transgender actress and influencer Dylan Mulvaney‘s body, recreating Mulvaney’s 2023 Bud Light promotional image.
It followed a joke Trump made two days earlier during the rescheduled White House Correspondents’ Association Dinner at the Waldorf Astoria in Washington, D.C.
After congratulating Collins on winning the WHCA award for broadcast journalism for her coverage of Trump’s February 2025 meeting with Ukrainian President Volodymyr Zelenskyy, Trump told the audience, “I said, ‘Kaitlin, do you ever smile?’ Smile. You have a nice position. You’re at CNN fake news. You should be a happy person. So smile, Kaitlan. Just smile.”
Trump also joked that he initially thought Collins had landed “a major new sponsorship, but then I informed her that it wasn’t her on the Bud Light can, it was Dylan Mulvaney.”
Christie and Springsteen mocked in fake concert image
Trump next shared an AI-generated image showing a disheveled-looking Springsteen performing onstage while a grease- and mustard-stained Christie unsuccessfully attempted to high-five the musician. Signs in the image read “Bored in the USA” and “Bruce Still Rocks! Us to Sleep.”
Referring to Springsteen, he said, “What about Bruce Springsteen? What the hell happens to that guy? He looks like h***. I’m sure he does not like the way I look. I don’t look so bad.”
He added that Springsteen’s recent tour “has been renamed: Bored in the USA.” Trump also referenced Christie trying to high-five Springsteen at a concert and being left hanging.
Late-night hosts and O’Donnell targeted next
Trump then posted several images of himself wearing a red “Trump 2028” hat before sharing one depicting Colbert, Kimmel and Fallon as disheveled panhandlers holding signs reading “Talentless, not funny, ex comedians need money” in front of a wall spray-painted with “Late Night Is Over.” During the correspondents’ dinner, Trump separately described Kimmel and Fallon as “sick people.”
He also shared an image portraying O’Donnell writing a letter addressed to “my dearest Donald” while surrounded by Irish memorabilia, including a Guinness beer and a leprechaun figure, referencing her move to Ireland.
O’Donnell has said she relocated to Ireland with her youngest child in January 2025 after Trump’s return to the White House, describing the move as self-imposed political exile.
Posts turn to Iran military imagery
Trump also shared an AI-generated image depicting a strike on Iran’s Kharg Island, a major oil export terminal in the Persian Gulf.
Additional posts showed simulated U.S. strikes on Iranian vessels, while another depicted Trump seizing control of an oil tanker as Iranian officials jumped overboard. The image was captioned, “It’s our tanker now!”
Other graphics portrayed Trump as a battlefield commander wearing a hat labeled “FAFO” and compared previous U.S. wars with what the posts suggested were shorter, lower-casualty conflicts under his leadership.
Expert analysis of Trump’s strategy
Media analysts say Trump’s use of AI imagery is part of a broader messaging strategy.
Nick Cull, a professor of communication at USC Annenberg, told BuzzFeed the posts were “the visual equivalent of his version of the classic propaganda tactic of name-calling.”
Cull said Trump combines name-calling, bandwagoning and glittering generalities to amplify his political messaging.
The Wall Street Journal previously found that about one in 10 of Trump’s Truth Social posts contain direct insults, often using terms such as “crooked,” “loser,” or “low IQ.”