'My dearest Donald': Trump drops a Rosie O'Donnell letter nobody saw coming

WASHINGTON, DC: President Donald Trump, on Sunday, July 26, once again turned his long-running feud with comedian Rosie O'Donnell into internet theater.

This time, he shared a satirical meme on Truth Social imagining O'Donnell writing him an affectionate letter beginning with the words, "My dearest Donald."

Packed with Irish stereotypes, playful signs, and political jabs, the image revives one of America's longest-running celebrity rivalries, one that neither side appears ready to let go.

Trump's hilarious take on Rosie O'Donnell

Trump turned one of his oldest celebrity rivalries into an imaginary fan moment on Sunday, sharing a cartoon that shows Rosie O’Donnell doing something almost impossible to picture, sending him a flattering message.

The meme places O’Donnell inside an over-the-top Irish-themed setting, complete with shamrocks, Guinness imagery, and Ireland references, while she appears to be writing a note addressed to the president.

The fictional letter reads, “Dear President Trump, You’re truly one of a kind! XOXO, Rosie,” with a thought bubble above her adding, “My dearest Donald.”

The punchline relies entirely on the fact that it is the opposite of reality.

O’Donnell and Trump have been trading public criticism for nearly 20 years, with the comedian frequently attacking Trump and becoming one of his most recognizable celebrity opponents.

The meme also adds another political jab by showing O’Donnell wearing a shirt marked “TDS Forever,” a reference to the phrase “Trump Derangement Syndrome” often used by Trump supporters against those who criticize him.

The post appears to reference O’Donnell’s move to Ireland last year while turning their long-running clash into a fictional reunion that never happened. 

A rivalry that refuses to fade

Trump’s latest Rosie O’Donnell meme works because it taps into a rivalry that has been playing out for nearly two decades.

Their feud began in 2006 after O’Donnell criticized Trump during her time on 'The View', prompting a heated response from him that turned a disagreement into a long-running public battle.

Since then, the two have repeatedly traded blows across interviews, television appearances, and social media.

O’Donnell has spoken about the emotional toll of being a frequent target of Trump’s attacks, describing the years of public criticism as deeply affecting.

Their clash continued through Trump’s political rise and both of his presidencies.

After relocating to Ireland in 2025, O’Donnell said she had found distance from the political environment in the US, but Trump has continued referencing her in public remarks and online posts.