Trump and Rosie O’Donnell Rekindle Long-Standing Feud

President Donald Trump has once again engaged in his enduring conflict with comedian Rosie O’Donnell by sharing an AI-generated image on Truth Social. This action follows O’Donnell’s comments suggesting Trump’s health is deteriorating.

In the image, O’Donnell is portrayed in a medical examination room with a doctor resembling Trump. The doctor holds a clipboard titled a ‘Trump Derangement Syndrome Assessment.’ The assessment diagnoses O’Donnell with ‘Massive / Severe TDS,’ listing symptoms such as ‘irrational rage,’ ‘obsessive Trump fixation,’ ‘meltdown triggered by Trump news,’ and ‘complete loss of composure.’

The post seems to directly address remarks O’Donnell made during her appearance on the On With Kara Swisher podcast, where she speculated about Trump’s undisclosed health issues. O’Donnell stated, “And the fact that he’s falling asleep, that he’s physically ill… these are things that everyone around him knows.” She also questioned transparency concerning Trump’s condition.

A spokesperson for the White House has heard O’Donnell’s claims but no evidence has been presented to support the notion of Trump being ‘very physically ill.’

The use of ‘Trump Derangement Syndrome’ is often employed by Trump’s supporters to label what they perceive as irrational opposition. Some critics dispute the term, arguing it discredits genuine criticism of Trump and his policies.

Trump has a pattern of using memes, edited images, and AI-generated content to mock opponents on Truth Social, with Friday’s post continuing this trend.

Trump’s Health Discussed

In May, Trump claimed to be in “excellent health” after a routine medical exam. A White House memo from Captain Sean Barbabella praised Trump’s health status, asserting his capability to perform presidential duties.

In July 2025, the White House acknowledged Trump’s diagnosis of chronic venous insufficiency, a condition causing swelling in the lower legs, but ruled out serious conditions like deep vein thrombosis or heart disease.

A Feud Crossing Nearly Two Decades

The conflict between Trump and O’Donnell began in 2006 when O’Donnell criticized him over his handling of the Miss USA controversy on ABC’s The View. Trump responded with public insults, sparking a feud that persisted through various political campaigns including Trump’s presidency.

During the 2016 Republican primary, their rivalry became a topic of national discourse. Fox News moderator Megyn Kelly addressed Trump’s remarks about women, to which he noted some comments were directed at O’Donnell.

This longstanding animosity has seen insults exchanged through public appearances, social media, and numerous interviews. Both parties remain vocal critics of one another.

Contact Newsweek editors Rebecca Flood and Emma Lee-Sang for further information.