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By Alice Gibbs
Senior Reporter
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President Donald Trump has reignited his decades-long feud with comedian Rosie O'Donnell after sharing an AI-generated image mocking her days after she claimed he appeared to be in poor health.
Trump posted the image to his Truth Social account in the early hours of Friday morning. The AI-generated picture shows O'Donnell in what appears to be a medical examination room while a doctor resembling Trump stands beside her holding a clipboard labeled a "Trump Derangement Syndrome Assessment."
The mocked-up assessment diagnoses O'Donnell with a "Massive / Severe TDS" case and lists supposed symptoms including "irrational rage," "obsessive Trump fixation," "meltdown triggered by Trump news" and "complete loss of composure."
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The post appeared to be a direct response to remarks O'Donnell made earlier this week during an interview on the On With Kara Swisher podcast, in which she suggested Trump was suffering from undisclosed health issues.
"People are tired of his act, I think," host Swisher said during the podcast. O'Donnell responded: "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.”
The comedian, who has been one of Trump's most outspoken celebrity critics for years, also questioned whether those around the president were being fully transparent about his condition.
Newsweek reached out to the White House and Rosie O'Donnell via email for comment.
Trump Uses Familiar Attack Line
The phrase "Trump Derangement Syndrome" has become a common refrain among the president's supporters and allies, who use it to describe what they view as obsessive or irrational opposition to Trump.
Critics of the term argue it is deployed to dismiss legitimate criticism of the president and his policies.
Trump has frequently used memes, edited images and AI-generated content on Truth Social to ridicule political opponents, critics and media figures. Friday's post targeting O'Donnell continues that pattern while reviving one of the most famous personal feuds of his public life.
What Has Donald Trump Said About His Health?
O'Donnell's comments come months after the president reported that he is in “excellent health” following his annual medical exam in May.
In a White House memo, Captain Sean Barbabella wrote that Trump, who is now 80, had "strong cardiac, pulmonary, neurological and overall physical function,” and added that he was “fully fit to carry out all duties of the Commander-in-Chief and Head of State.”
In July 2025, the White House disclosed that Trump had been diagnosed with chronic venous insufficiency, a common vein condition that can cause swelling in the lower legs. The announcement followed public speculation after photographs appeared to show swelling around the president's ankles and bruising on his hands. White House press secretary Karoline Leavitt said testing found no evidence of deep vein thrombosis, arterial disease, heart failure or kidney problems.
O'Donnell offered no evidence to support her assertion that Trump is "very physically ill," and the White House has not indicated that the president is suffering from any serious or undisclosed medical condition.
...
A Feud Dating Back Nearly Two Decades
The animosity between Trump and O'Donnell stretches back to 2006, when O'Donnell criticized Trump on ABC's The View over his handling of controversy involving Miss USA winner Tara Conner.
Trump responded with a barrage of media interviews and public insults, launching a feud that would continue through the reality television era, multiple election campaigns and Trump's presidency.
Their rivalry became a national political talking point during the 2016 Republican primary campaign when Fox News moderator Megyn Kelly challenged Trump over past remarks about women.
Trump responded by saying that some of the comments in question had been directed toward O'Donnell, prompting laughter from the debate audience and further cementing the pair's feud in popular culture.
Over the years, both have repeatedly traded insults through television appearances, social media posts and interviews.
Timeline: Donald Trump and Rosie O'Donnell's Long-Running Feud
- December 2006: The feud begins after O'Donnell criticizes Trump on ABC's The View over his handling of controversy involving Miss USA winner Tara Conner.
- Late 2006-2007: Trump fires back in television interviews and press appearances, calling O'Donnell insulting names and threatening legal action. The pair exchange public attacks for months.
- 2011: Trump mocked O'Donnell after news of her engagement saying "I feel sorry for Rosie's new partner."
- 2014-2015: As Trump launches his presidential campaign, O'Donnell continues criticizing him in interviews and on social media.
- August 2015: During the first Republican primary debate, Fox News moderator Megyn Kelly asks Trump about past comments he made about women. Trump responds that some were directed at O'Donnell, drawing one of the night's most memorable moments and bringing their feud to a national political audience.
- 2016 Presidential Election: O'Donnell repeatedly campaigns against Trump's candidacy, while Trump continues referencing her in interviews and public appearances.
- 2017-2020: During Trump's first term, O'Donnell remains one of his most vocal celebrity critics, frequently commenting on his presidency online and in media appearances.
- 2024 Presidential Campaign: O'Donnell continues criticizing Trump as he campaigns for a return to the White House.
- 2025: After Trump's return to office, O'Donnell announces she has moved to Ireland, citing political concerns and opposition to the president.
- August 2026: O'Donnell says during an interview with Irish broadcaster On With Kara Swisher podcast that "everyone around him knows he is very physically ill" and claims Trump's health appears to be deteriorating.
- August 7, 2026: Trump responds by posting an AI-generated image on Truth Social depicting O'Donnell receiving a diagnosis of severe "Trump Derangement Syndrome," reigniting one of America's longest-running celebrity-political feuds.
Contact Newsweek editors on this story: Rebecca Flood and Emma Lee-Sang
Update 08/07/26 05:40 a.m. ET: This story was updated with a timeline.
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