President Donald Trump has once again sparked his long-standing feud with comedian Rosie O’Donnell. He shared an AI-generated image mocking her following her comments about his health. The image was posted on his Truth Social account early Friday morning.
The AI-generated picture depicts O’Donnell in what seems to be a medical exam room. A doctor resembling Trump stands beside her, holding a clipboard labeled ‘Trump Derangement Syndrome Assessment.’ This mock assessment diagnoses O’Donnell with a ‘Massive / Severe TDS’ case, listing symptoms such as ‘irrational rage’ and ‘obsessive Trump fixation.’
This post appears to respond directly to O’Donnell’s remarks made earlier in the week during an interview on the On With Kara Swisher podcast. During the interview, O’Donnell suggested that Trump might be dealing with undisclosed health issues.
People are tired of his act, I think,
host Swisher remarked, 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, a vocal critic of Trump for years, also questioned if those around him are transparent about his health condition. Newsweek has reached out to the White House and Rosie O’Donnell for comments.
Trump’s Familiar Attack Line
The term ‘Trump Derangement Syndrome’ is often used by Trump’s supporters to describe what they see as obsessive opposition to him. Critics, however, argue it is used to dismiss genuine criticism of the president and his policies.
Trump frequently uses memes, edited images, and AI-generated content on Truth Social to mock opponents, critics, and media figures. Targeting O’Donnell continues this pattern, reigniting one of his most famous personal feuds.
Donald Trump’s Health Updates
O’Donnell’s comments followed Trump’s announcement that he is in ‘excellent health’ after his annual medical exam in May. According to a White House memo, Captain Sean Barbabella stated Trump had strong cardiac, pulmonary, neurological, and overall physical function. He added that Trump is ‘fully fit’ for his duties as Commander-in-Chief.
In July 2025, the White House revealed Trump had chronic venous insufficiency, a common condition that causes swelling in the legs. This came after public speculation due to photos showing swelling around his ankles. White House press secretary Karoline Leavitt noted testing found no evidence of serious health issues.
O’Donnell gave no evidence to support her claims that Trump is ‘very physically ill,’ and the White House hasn’t reported any serious or undisclosed medical condition.
A Feud Over Nearly Two Decades
The animosity between Trump and O’Donnell dates back to 2006, when O’Donnell criticized Trump on ABC’s The View over a Miss USA controversy. Trump retaliated with media interviews and public insults, starting a feud that continued through reality TV, elections, and his presidency.
Their rivalry became a key political topic during the 2016 Republican primary campaign. Fox News moderator Megyn Kelly challenged Trump on his past remarks about women, leading him to note that some comments targeted O’Donnell. This sparked laughter from the audience and made the feud more prominent in popular culture.
Over the years, Trump and O’Donnell have repeatedly insulted each other via TV appearances, social media, and interviews.
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