Trump Posts AI Image Targeting Rosie O'Donnell, Reviving Decades-Long Feud

On August 7, 2026, former president Donald Trump uploaded an AI-generated illustration to his Truth Social platform that depicted comedian Rosie O'Donnell in a mock medical exam room. The image featured a doctor resembling Trump holding a clipboard labeled “Trump Derangement Syndrome Assessment” and listed fabricated symptoms such as “irrational rage” and “obsessive Trump fixation.” The post appeared to answer O'Donnell’s recent comments on the *On With Kara Swisher* podcast in which she suggested Trump was “very physically ill” and unfit to control the nuclear code.

Newsweek

The antagonism dates to December 2006, when O'Donnell criticized Trump on *The View* over his handling of a Miss USA controversy. Trump retaliated with televised insults and legal threats, and the exchange continued through the 2011 engagement mockery, the 2015 primary debates, and the 2016 election, during which O'Donnell campaigned against him. After Trump’s 2024 campaign, O'Donnell announced a move to Ireland in 2025, citing political concerns, and maintained her criticism into 2026.

Newsweek

O'Donnell’s allegation that Trump’s health was deteriorating was not accompanied by evidence. The memo followed a July 2025 disclosure that Trump had been diagnosed with chronic venous insufficiency, a vein condition causing leg swelling. Press secretary Karoline Leavitt clarified that testing found no signs of deep-vein thrombosis, arterial disease, heart failure, or kidney problems.

Newsweek

The episode illustrates how Trump continues to employ memes, edited images, and AI-generated content to counter critics, while the term “Trump Derangement Syndrome” remains a polarizing label used by his supporters and challenged by opponents as a dismissal of legitimate critique. The renewed spat underscores the intersection of celebrity culture, political rivalry, and emerging digital tactics in contemporary public discourse.

Newsweek