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Donald Trump’s Old Remarks About Princess Diana and Kate Middleton Comes Back to Haunt Him

(L) Princess Kate on the Royal Dais in Windsor, (R) Princess Diana wears an outfit in the colors of Canada; (Inset) President Donald Trump walks to Air Force One. Cover Image Source: Getty Images | (L) Samir Hussein; (R) Bettman; (Inset) Kevin Dietsch
(L) Princess Kate on the Royal Dais in Windsor, (R) Princess Diana wears an outfit in the colors of Canada; (Inset) President Donald Trump walks to Air Force One. Cover Image Source: Getty Images | (L) Samir Hussein; (R) Bettman; (Inset) Kevin Dietsch
Sep. 19 2025, Published 04:30 AM. ET
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The royal family went all out for Donald Trump’s recent state visit. A state banquet at Windsor Castle, a full carriage procession, and a royal salute, it was a spectacle designed to show off Britain at its most ceremonial. However, Trump’s past words about the two most beloved women in the British monarchy, Princess Diana and Kate Middleton, continue to haunt him. 

Prince William and Kate Middleton officially welcome Donald and Melania Trump. (Cover Image Source: Getty Images| Ian Vogler - WPA Pool)
Prince William and Kate Middleton officially welcome Donald and Melania Trump. (Image Source: Getty Images| Ian Vogler - WPA Pool)

Trump’s controversial history with Diana dates back to the 1990s. According to royal author Christopher Andersen's The King: The Life of Charles III, Trump 'aggressively pursued' the Princess after her separation from then-Prince Charles. Reports at the time even suggested she was eyeing an apartment in Trump Tower, though many suspected those claims were little more than self-serving PR. Diana’s brother, Charles Spencer, later made clear how little she thought of the politician. Spencer tweeted in 2023, “Surprised to hear that Donald Trump is apparently claiming that my late sister Diana wanted to ‘kiss his arse,’ since the one time she mentioned him to me — when he was using her good name to sell some real estate in New York — she clearly viewed him as worse than an anal fissure.”



 

If that incident painted Trump as tone-deaf, his remarks about Middleton years later confirmed it. In 2012, topless photos of Middleton sunbathing during a holiday in Provence with Prince William were taken illegally and splashed across a French magazine, Closer. A court later ruled it was an invasion of privacy, awarding damages of around $53,000 to the couple. Trump, however, decided to weigh in on X (formerly Twitter). He wrote, “Kate Middleton is great — but she shouldn’t be sunbathing in the nude — only herself to blame.” He didn’t stop there, adding, “Who wouldn’t take Kate’s picture and make lots of money if she does the nude sunbathing thing? Come on, Kate!”

Screenshot of the tweet by Donald Trump. (Image Source: X)
Screenshot of the tweet by Donald Trump. (Image Source: X | @realDonaldTrump)

Reportedly, William was furious about it. Andersen detailed, “Trump’s criticism of Kate resulted in what one Clarence House butler referred to as ‘torrents of profanity’ from both Prince Charles and his sons.” He also alleged that this wasn’t the first time the royals had openly expressed ire towards Mr. Trump. Before the 2012 incident, Andersen explained that Trump’s comments about Diana were also not well-received by the royal family.

“It didn’t help that Trump had aggressively pursued Princess Diana after her divorce — overtures that were rebuffed — and claimed later on a radio program that he could have ‘nailed her if I wanted to,’ but only if she passed an HIV test,”  Andersen wrote. By 2017, tensions hadn’t cooled. According to Andersen’s book, Charles and his sons were so wary of Trump’s presence on British soil that they “burned up the phone lines between Clarence House and Kensington Palace.”

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