Trump attacks GOP judge and Emmy-winning comedian in wild new AI posting spree

President Donald Trump unleashed a flurry of AI-generated images on Truth Social Saturday, targeting a federal judge blocking his White House construction plans, mocking Rosie O'Donnell with a transphobic jab, and taking a shot at Barack Obama's presidential library.

The most substantive post concerned U.S. District Judge Richard Leon, who has blocked Trump's proposed White House rooftop drone base — part of the broader $400 million White House renovation project that also includes a ballroom. Trump posted an AI rendering of military drones parked on the White House roof under the label "Drone Port," writing: "This will someday save Washington. Judge Leon has to get out of the way, and FAST. He is putting our Country in danger!"

Leon ruled in April that Trump lacked the legal authority to build the ballroom without congressional approval. The Justice Department has pressed him to lift the injunction, invoking national security — an argument Trump amplified Saturday with the AI imagery and a separate post showing military helicopters flying in formation, presumably over Washington.

In a separate post, Trump shared an AI-generated collage depicting Rosie O'Donnell daydreaming about him in various domestic settings — doing dishes, reading, driving — with his image appearing in thought bubbles above her head. The caption read: "She (?) is OBSESSED!" The question mark placed after "She" was a transphobic reference to O'Donnell, who has been a Trump antagonist for decades.

Trump also posted a black-and-white photo of himself leaning over a desk with the quote: "Just sit back and relax, it will all work out well in the end — It always does!" — an apparent attempt at reassurance directed at his base amid ongoing legal battles and the Iran war.

Finally, Trump posted an AI image of what appeared to be a massive garbage can topped with a black trash bag, surrounded by a tent encampment, with a Chicago skyline in the background. The caption: "The Barack Hussein Obama Library, in 10 years, when fully matured!" — using Obama's middle name in the manner Trump has long deployed as a dog whistle.