Trump shares AI-generated posts mocking Fallon, Colbert and many more in social media spree

Trump's Sunday posting spree also included images related to Iran and with 'Trump 2028' messaging
Donald Trump went on a posting spree on Truth Social on Sunday, July 26, sharing AI-generated images targeting Stephen Colbert, Jimmy Fallon, Jimmy Kimmel, and Rosie O'Donnell, among others (Getty Images, Donald Trump/Truth Social)
Donald Trump went on a posting spree on Truth Social on Sunday, July 26, sharing AI-generated images targeting Stephen Colbert, Jimmy Fallon, Jimmy Kimmel, and Rosie O'Donnell, among others (Getty Images, Donald Trump/Truth Social)

WASHINGTON, DC: President Donald Trump shared a series of AI-generated images on Truth Social on Sunday, July 26, targeting several public figures, including current and former late-night television hosts Jimmy Kimmel, Jimmy Fallon, and Stephen Colbert.

The posts came two days after Trump's appearance at the White House Correspondents' Dinner, where he made remarks involving CNN anchor Kaitlan Collins that were later echoed in one of the AI-generated images shared on his social media account. 

President Donald Trump gestures during a meeting of his Cabinet in the Cabinet Room of the White House on December 02, 2025 in Washington, DC. A bipartisan Congressional investigation has begun regarding Secretary of War Pete Hegseth's role in ordering U.S. military strikes on small boats in the waters off Venezuela that have killed scores of people, which Hegseth said are intended
President Donald Trump gestures during a meeting of his Cabinet in the Cabinet Room of the White House on December 2, 2025, in Washington, DC (Chip Somodevilla/Getty Images)

AI-generated posts target late-night hosts and political critics

Among the images Trump shared was an AI-generated depiction of comedians Stephen Colbert, Jimmy Kimmel, and Jimmy Fallon portrayed as homeless individuals holding signs reading, "Talentless, not funny, ex comedians need money." The image also featured graffiti on a wall behind them stating, "Late Night Is Over."



The presdient also posted AI-generated images depicting former New Jersey Gov Chris Christie alongside Bruce Springsteen, including one showing Christie attempting to high-five the musician beneath a sign reading "Bored in the USA."



Another image portrayed Christie and Rep Jerry Nadler (D-NY) in a fictional boxing match labeled the "Cheesecake Championship."



Trump also shared an AI-generated image targeting Rosie O'Donnell, depicting the comedian and actress in Ireland writing a letter addressed, "My dearest Donald, you're truly one of a kind," while surrounded by Irish-themed items.



In the image, she is shown wearing a sweatshirt reading "TDS Forever," an apparent reference to the term "Trump Derangement Syndrome." 

Posts also included Iran-themed images, 'Trump 2028' messaging

Later in the posting spree, Trump's account shifted to AI-generated images related to Iran. One image showed the Republican leader aboard a wooden boat in the Strait of Hormuz raising the American flag as an Iranian flag lay beneath him, captioned, "It's our tanker now!"



Another depicted Trump standing with a raised fist beside an Iranian oil tanker carrying the same message. Additional AI-generated images portrayed military-themed scenes involving Iranian vessels and Kharg Island.



The social media activity followed reports that military operations against Iran had halted after 13 consecutive days of exchanges of strikes between the two countries. The series of posts also featured AI-generated images promoting Trump's "Trump 2028" branding and depicting him in fictional historical settings.

Another AI-generated image took the form of a fictional movie poster titled "Trump X Washington: A Time Travel Epic." It depicted George Washington appearing to fall from Mount Rushmore as Trump reaches out to pull him to safety. 



The posting spree also included an AI-generated collage showing Trump at different stages of his life, from teen years to the presidency, accompanied by the caption, "The Man Who Saved America."



The president also shared multiple AI-generated images of himself wearing "Trump 2028" hats in different colors, including red and pink, alongside another image from the White House Correspondents' Dinner showing him wearing a "Trump 2028" cap.



The spree came just days after he first wore the hat at the White House Correspondents' Dinner while joking about serving a fourth term.

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