Prince Harry has never shied away from speaking his mind, but his recent jokes about former President Donald Trump may have crossed a line. While the Duke of Sussex has traded barbs with Trump before, his latest attempts at humor reveal two things: he’s not particularly funny, and he’s now firmly on Trump’s radar.
Despite appearances, Harry and Trump share some similarities they’ve both built public personas around their names and status, and both have faced scrutiny over their privileged backgrounds. Trump’s billionaire empire didn’t spring from nothing; he received a £1 million loan from his father in the 1970s. Similarly, Harry was born into royalty, with all the advantages that come with being the second son of a future king. Neither man is exactly a “rags-to-riches” success story.
Where they differ dramatically is in personality. Trump is brash and self-confident, while Harry often comes across as self-pitying. His memoir, Spare, has been criticized for its “woe is me” tone, reinforcing the image of a royal who struggles with public life despite living in one of the most protected families in the world.
Trump has not hidden his opinions about Harry. In 2022, he told Piers Morgan that Harry was “whipped like no person he has ever seen,” and in 2025, he doubled down, adding that Harry “has enough problems with his wife.” Following revelations from Spare about Harry’s past drug use, Trump hinted that any discrepancies on his visa could have consequences. While Harry is a lawful US resident, he is neither a citizen nor a green card holder, leaving him in a precarious position if Trump decided to act.
Meanwhile, Harry’s attempts at humor haven’t landed as he might have hoped. On The Late Show with Stephen Colbert, he called Americans “obsessed with royalty” and joked they had “elected a king,” a clear jab at Trump. The audience reaction was lukewarm, and US commentators criticized Harry for overstepping, suggesting he has isolated himself from the Royal Family by going rogue. A recent sketch on the show, portraying him auditioning for a Hallmark Christmas movie, also fell flat.
Since stepping back from royal duties in 2020, Harry and Meghan have raised their family in Montecito, California. But with Trump’s history of long-game retaliation, any misstep could carry consequences. Whether through media attacks, public humiliation, or immigration scrutiny, the former president has shown he’s capable of striking back coldly and Harry may now be in his sights.
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