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Trump’s Latest Strange AI Images Attack Stephen Colbert, ...
Zachary Folk · 2026-05-24 · via Forbes - Business

Topline

President Donald Trump went on another posting spree of strange seemingly-AI generated images again on Friday and Saturday morning—this time posting a crude caricature of Rep. Ro Khanna, D-Calif., a map of the Middle East showing Iran covered by an American flag, and an ominous image of the president peeking out above an apparent landscape of Greenland.

The president appears to be fixating once again on Greenland, the Danish territory in the Arctic.

AFP via Getty Images

Key Facts

Trump began by posting an AI-generated graphic of his proposed “Golden Dome” missile defense system, but this time only covering the grounds of the White House instead of the entire country.

He followed that up with the strange image of Greenland, which he posted again on Saturday morning—reigniting the tensions with the autonomous Danish territory the president has previously said the U.S. needs for national security, including the Golden Dome.

In another strange post on Saturday morning, the president posted a map of the Middle East with Iran covered in an American flag, combined with the caption: “The United States of the Middle East?”—coming just after Iranian negotiators said they would refuse a compromise with the U.S. in the ongoing peace negotiations.

In an AI generated video, Trump then appears to throw outgoing “Late Show” host Stephen Colbert into a dumpster before dancing to “YMCA,” posted hours after Colbert’s final broadcast.

On Saturday morning, Trump again posted the “Hello, Greenland” image alongside the caricature of Khanna, the congressman who introduced the Epstein Files Transparency Act, calling the California Democrat a “dumocrat” and and “sleazebag.”

Key Background

Trump's fixation on Greenland, an autonomous territory controlled by Denmark but governed by its own parliament, began during his first term but ramped up considerably during his first year back in office in 2025. Greenland and Denmark have consistently refused the Trump administration’s demands to hand over the territory. Denmark is a member of NATO, and the U.S. has maintained a military presence on the island since the Cold War. The three sides have been involved in closed-door negotiations since January over the island’s future, the New York Times reported, although it remains to be seen if the talks will produce a deal the president will approve of.

Tangent

Louisiana Gov. Jeff Landry, Trump’s special envoy to Greenland, took his first trip to the Arctic territory last week, where he reportedly received a cold reception from locals. After landing, Landry told reporters Trump told him to “go over there and make as many friends as we can get.” In a bizarre video circulating after his trip, Landry walked the streets of Greenland’s capital Nuuk and handed out chocolate chip cookies to baffled Greenlandic children. “If you come to the Governor’s Mansion in Louisiana, you can have all the chocolate chip cookies you can eat,” he told a group of children in a video circulating on social media.

Crucial Quote

Speaking to Fox News on Friday, Landry reframed the U.S.’s interest in Greenland as important, due to the island’s energy resources. The Louisiana governor said Greenland’s resources would “bring wealth to them [Greenlanders], just like oil and gas brought wealth to Louisiana and to the nation.” He said Trump “wants a deal. Greenland needs a deal… Greenland could be exporting 2 million barrels of oil a day right now. Think about what that would mean. Think about what kind of pressure that would relieve in the Strait of Hormuz, what kind of leverage that would give the Western Hemisphere and America, think about the help that would give to Europe right now.” Landry claimed the U.S. could begin producing barrels of oil in Greenland “within 10 months or so.” Greenland previously suspended oil exploration after 50 years in 2021 over both environmental concerns and analysis that extraction would lead to low profits or a loss, Reuters reported at the time.

Further Reading

ForbesTrump Attacks Obama, Newsom And Other Democrats In Another Weekend AI Posting SpreeBy Siladitya Ray

ForbesTrump Attacks Biden With AI-Generated Post And Pushes ‘Autopen’ Claims AgainBy Siladitya Ray

ForbesBizarre String Of Trump Posts Includes Photo Swimming Shirtless In D.C. Reflecting PoolBy Mary Whitfill Roeloffs