Trump Revives Longstanding Feud with Rosie O’Donnell
President Donald Trump has reopened a long-running conflict with comedian Rosie O’Donnell by sharing an AI-generated image mocking her. This followed O’Donnell’s comments suggesting Trump appeared to be in poor health. Trump posted the image on his Truth Social account early Friday morning.
The AI-generated image depicts O’Donnell in an examination room with a doctor resembling Trump. The doctor is shown holding a clipboard labeled “Trump Derangement Syndrome Assessment.” The assessment humorously diagnoses O’Donnell with a “Massive / Severe TDS” case, listing 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 remarks in a podcast interview where she described Trump as possibly having undisclosed health issues. Host Kara Swisher mentioned that people were tired of Trump’s act, to which O’Donnell added, “And the fact that he’s falling asleep, that he’s very physically ill, that he doesn’t look like he’s long for this earth, that he shouldn’t be the man in control of the nuclear code. Like, these are things that everyone around him knows.” O’Donnell has been one of Trump’s vocal critics for many years.
Newsweek reached out to the White House and Rosie O’Donnell for comments on the matter.
Trump’s Use of ‘Trump Derangement Syndrome’
The term “Trump Derangement Syndrome” is popular among the president’s supporters. They use it to describe perceived irrational opposition to Trump. Critics argue the term is used to dismiss legitimate criticism of Trump and his policies.
Trump frequently uses memes and AI-generated content on Truth Social to mock opponents and critics. The recent post about O’Donnell follows this pattern, reviving one of his most well-known personal feuds.
Trump’s Health Allegations
O’Donnell’s health-related comments came months after Trump declared he was in “excellent health.” A White House memo by Captain Sean Barbabella noted Trump, now 80, had “strong cardiac, pulmonary, neurological, and overall physical function.” He was deemed “fully fit to carry out all duties of the Commander-in-Chief and Head of State.”
In July 2025, it was revealed that Trump had chronic venous insufficiency, causing swelling in the lower legs. This came after photos showed swelling around his ankles and bruising on his hands. Press secretary Karoline Leavitt stated there was no evidence of deep vein thrombosis or serious ailments.
O’Donnell didn’t provide evidence for her claims about Trump’s health, and the White House has not suggested any serious undisclosed conditions.
A Feud Spanning Nearly Two Decades
The tension between Trump and O’Donnell began in 2006 when O’Donnell criticized Trump on ABC’s The View. She questioned his response to the Miss USA winner Tara Conner’s controversy. Trump countered with media interviews and public insults, sparking a feud lasting through multiple campaigns and his presidency.
During the 2016 Republican primary, Megyn Kelly challenged Trump on his remarks about women, mentioning that some were directed at O’Donnell. This led to further public amusement and solidified their conflict in political discourse.
Over the years, both continued exchanging insults via television, social media, and interviews.
Contact Newsweek editors Rebecca Flood and Emma Lee-Sang for more information.