President Donald Trump has revived his long-standing conflict with comedian Rosie O’Donnell by sharing an AI-generated image mocking her. This comes shortly after O’Donnell commented on Trump’s alleged health issues. Trump posted the image on his Truth Social account early Friday. The AI picture depicts O’Donnell in a medical setting, with a Trump lookalike holding a ‘Trump Derangement Syndrome Assessment’ clipboard.
The assessment mockingly diagnoses O’Donnell with a severe case of ‘TDS,’ listing supposed symptoms like ‘irrational rage’ and ‘obsessive Trump fixation.’ This appears to be a direct response to O’Donnell’s remarks during the On With Kara Swisher podcast. O’Donnell implied Trump could be facing undisclosed health problems, questioning the transparency of those around him.
During the podcast, host Kara Swisher suggested people were ‘tired of Trump’s act.’ O’Donnell agreed, claiming Trump appeared physically ill and unfit for his responsibilities. ‘He doesn’t look long for this earth,’ said O’Donnell, expressing concerns about his control over the nuclear codes.
Attempts to reach the White House and O’Donnell for comments by Newsweek were unsuccessful. Trump’s use of ‘Trump Derangement Syndrome’ as an attack term is recognized among his supporters, describing those with what they see as irrational opposition to him. Critics argue this term dismisses legitimate criticisms.
Trump routinely employs memes and AI-generated content on Truth Social to mock critics and political adversaries, continuing his practice with this post targeting O’Donnell. This incident revives a notable feud from his past.
Trump’s Health vs. Public Speculation
O’Donnell’s assertions emerged months after Trump reported being in ‘excellent health’ post his annual May medical exam. A White House memo from Captain Sean Barbabella described Trump, aged 80, as having robust cardiac, pulmonary, neurological, and overall fitness.
In July 2025, the White House revealed Trump’s chronic venous insufficiency diagnosis, a vein condition causing leg swelling. This followed speculations triggered by photographs showing Trump’s swollen ankles and bruised hands. Press Secretary Karoline Leavitt noted further testing showed no severe conditions.
Despite O’Donnell’s claims, she provided no evidence regarding Trump’s health, and the White House has not acknowledged any serious undisclosed medical issues.
A Feud That Began in 2006
The Trump-O’Donnell feud dates back to 2006, when O’Donnell criticized Trump on ABC’s The View regarding his handling of Miss USA Tara Conner. Trump’s response included numerous media interviews and public insults. The rivalry persisted through numerous public engagements, including election campaigns and Trump’s presidency.
This conflict became notable during the 2016 Republican primary. Fox News moderator Megyn Kelly questioned Trump about past remarks on women, where Trump mentioned some comments were directed at O’Donnell, prompting audience laughter.
Over the years, both have continuously exchanged insults through various public platforms. This ongoing feud continues to capture public attention as a notable element of Trump’s public interactions.