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Prince Harry Slammed for Making Distasteful Jokes About Trump at Recent Outings: ‘Wasn't Wise!’

Prince Harry attends The Invictus Games Foundation 10th Anniversary Service; (Inset) Donald Trump on day 1 of his state visit to the UK. Cover Image Source+Inset: Getty Images| Max Mumby/Indigo
Prince Harry attends The Invictus Games Foundation 10th Anniversary Service; (Inset) Donald Trump on day 1 of his state visit to the UK. Cover Image Source+Inset: Getty Images| Max Mumby/Indigo
Dec. 10 2025, Published 02:47 AM. ET
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Prince Harry and Donald Trump have long been far from cordial, often trading jibes at public events. Most recently, on December 3, during a surprise appearance on The Late Show with Steven Colbert, Harry referenced Trump's 'authoritarian' leadership while joking about the 'No King's' protests. Two days later, at a British American Business Council speech, he quipped that football fans must behave to 'get past ICE.' Weighing in on his repeated swipes, royal expert Richard Fitzwilliams believes Harry's unwarranted public shade was in poor taste.

Prince Harry walks behind Queen Elizabeth II's coffin. (Cover Image Source: Getty Images | Max Mumby)
Prince Harry walks behind Queen Elizabeth's coffin during her funeral service in 2022. (Image Source: Getty Images | Max Mumby/Indigo)

Harry and Meghan Markle have long been vocal about their disdain for Trump's dictator-like leadership. Commenting on his recent cameos, Fitzwilliams told the Daily Express, "Harry's been an extra twice in the last week, once in the critically excoriated With Love, Meghan, and the other on Stephen Colbert's The Late Show." Criticizing Harry's latest digs, he added, "The former was pretty meaningless, although we learnt what foods he doesn't like. The latter was silly, and it wasn't wise to mock Donald Trump!" Meanwhile, the US President maintains a good rapport with the royal family, often expressing admiration for them, though that sentiment doesn't extend to the Sussexes.

King Charles and Donald Trump during a State Banquet at Windsor Castle. (Cover Image Source: Getty Images| Yui Mok - WPA Pool
King Charles and Donald Trump during a state banquet at Windsor Castle. (Image Source: Getty Images| Yui Mok - WPA Pool)

Similarly, royal expert Kinsey Schofield echoed Fitzwilliam's sentiments, pointing out that Harry's 'reckless' digs were in 'terrible judgment.' She told Fox News, "Harry's jab at President Trump on Colbert wasn't clever – it was reckless. Honestly, how does he think he can hold on to a royal title while taking public swipes at the head of a foreign government?" She added, "Buckingham Palace put significant effort into a major state visit for President Trump to support diplomatic relations. And, frankly, it's a slap to President Trump as well, considering he agreed to ease up on Harry's immigration situation out of personal respect for King Charles."

Prince Harry appears on the The Late Show with Stephen Colbert. (Cover Image Source: YouTube | The Late Show with Stephen Colbert)
Prince Harry makes an appearance on 'The Late Show with Stephen Colbert.' (Image Source: YouTube | The Late Show with Stephen Colbert)

Harry's scathing Trump jibe on The Late Show with Steven Colbert drew mixed reactions, with many in the audience booing him over the joke. During the segment, he walked on stage and quipped, "I really thought this was the audition for the Gingerbread Prince saves Christmas in Nebraska." He further joked that he once considered acting because he knew how 'obsessed' Americans were with royalty and holiday movies. After Colbert brushed that aside, the Duke delivered his punchline, "Really? I heard you elected a king." Harry was referring to the 'No Kings' protest in the US, a protest moment against the President's authoritarian leadership.



Clearly not done with letting the President off the hook, the Duke once again referenced Trump's controversial stance on migrants during a speech for the British American Business Council gathering on December 5. Referencing England and Scotland's qualification for next year's tournament, he said, "Next year, I know we are looking forward to welcoming more Brits from across the pond." Taking a brutal jab, he quipped, "Provided they behave, and if they make it through customs, and past ICE," sparking laughter from the audience. He continued, "The British are coming, hungry for victory, and they're thirsty."

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