Trump’s Feud with Rosie O’Donnell: A Continued Battle

President Donald Trump has reignited his longstanding conflict with comedian Rosie O’Donnell by sharing an AI-created image mocking her. This comes shortly after O’Donnell claimed his health seemed poor. Trump’s post on Truth Social features a picture of O’Donnell in something resembling a medical exam room, with a doctor who looks like Trump holding a clipboard labeled “Trump Derangement Syndrome Assessment.”

The assessment portrays O’Donnell as having “Massive / Severe TDS,” detailing symptoms such as “irrational rage,” “obsessive Trump fixation,” “meltdown triggered by Trump news,” and “complete loss of composure.” This post seems to directly respond to O’Donnell’s recent remarks on Kara Swisher’s podcast, where she suggested Trump might be unwell.

“People are tired of his act, I think,” Swisher stated. O’Donnell added, “And the fact that he’s falling asleep, that he’s physically ill, doesn’t look like he’s long for this earth, shouldn’t be controlling the nuclear code. Like, these things everyone around him knows.”

O’Donnell has been an outspoken critic of Trump for years, questioning the transparency of those around him regarding his health. Newsweek attempted to contact both the White House and O’Donnell for comments.

Trump’s Familiar Attack Line

“Trump Derangement Syndrome” often surfaces among Trump supporters to describe what they consider irrational opposition to him. Critics argue it’s used to dismiss valid critiques of Trump’s policies. Trump has a history of using memes and AI-generated content on Truth Social to poke fun at adversaries, continuing this trend with O’Donnell.

Trump’s Health Statements

O’Donnell’s comments follow Trump’s report of “excellent health” after his annual exam. Captain Sean Barbabella’s memo highlighted Trump’s strong physical capabilities, stating he’s fully fit for his role. In 2025, chronic venous insufficiency was disclosed as a vein condition causing leg swelling. Scrutiny arose from public photos showing ankle swelling and hand bruising; tests ruled out thrombosis and other serious conditions.

No evidence supports O’Donnell’s claim of Trump’s serious illness, and the White House hasn’t indicated any undisclosed medical issues.

A Decades-Long Feud

Trump and O’Donnell’s conflict dates back to 2006 after O’Donnell criticized Trump on ABC’s The View regarding Miss USA Tara Conner’s controversy. Trump retaliated with media insults, prolonging their feud through reality TV and election seasons.

Their rivalry became prominent in the 2016 Republican primary when Megyn Kelly confronted Trump about previous remarks on women. Trump mentioned some remarks targeted O’Donnell, eliciting laughter and further embedding their conflict in culture. Over the years, they’ve exchanged insults in media and interviews.

For inquiries regarding this story, contact Rebecca Flood or Emma Lee-Sang at Newsweek.