The relationship between Prince Harry, the Duke of Sussex, and President Donald Trump has historically been strained, punctuated by barbed comments and open political animosity. That dynamic is unlikely to improve following the Duke’s appearance on Stephen Colbert’s late-night show on Wednesday, where Harry delivered a clear, pointed jab at the former President.
Since stepping away from royal duties, the Duke and Duchess of Sussex spent a short time in Canada before settling into their permanent residence in Montecito, California. Despite his established life in the U.S., the Duke has previously revealed that he has no immediate plans to apply for American citizenship—a position that exists under the cloud of past threats from Donald Trump regarding his potential deportation.
The Immigration Battle: Spare, Drugs, and the DHS Lawsuit
The tension surrounding Prince Harry’s immigration status escalated in 2023 when the American conservative think tank, The Heritage Foundation, filed a lawsuit against the Department of Homeland Security (DHS) demanding access to Harry’s immigration records. The legal challenge centered on the application process for certain American visas, which typically requires applicants to disclose any past drug use—a factor that could potentially lead to the denial of the application.
In his memoir, Spare, the Duke had candidly revealed past use of various illicit substances and psychedelics, including cocaine, marijuana, and magic mushrooms. He also admitted to lying as a teenager about his cocaine use. Harry publicly excused this past drug use by linking it to the emotional burden and trauma he felt relating to the death of his mother, Princess Diana.
In September of last year, a court ruled that Harry’s specific visa application records were to remain private. Despite this ruling, Donald Trump weighed in heavily on the matter, suggesting the Prince could still face deportation if it was found that he had lied during his application process regarding his past drug use.
“We’ll have to see if they know something about the drugs, and if he lied they’ll have to take appropriate action,” Trump stated in March 2024, keeping the threat of official action alive.
Mockery on The Late Show
Just a month prior to that statement, Trump had clarified his position regarding the Duke should he win the upcoming 2024 presidential election in November, offering zero reassurance.
“I wouldn’t protect him. He betrayed the Queen. That’s unforgivable. He would be on his own if it was down to me,” Trump told the Express at the time, adding that he believed the Royal Family had been “too gracious” to Harry following “what he has done.”
Prince Harry has generally been circumspect when publicly discussing Donald Trump or offering his thoughts on a second potential presidential term. However, during his appearance on The Late Show with Stephen Colbert on Wednesday, the Duke delivered a surprisingly brutal comment directed squarely at the former President.
The segment featured a sketch where the comedian and the former Royal teamed up, with Harry pretending to audition to play a “Gingerbread Christmas Prince saves Christmas in Nebraska” in a fictional Hallmark movie. The sketch was used to point out what Harry characterized as the U.S.’s “obsession” with royalty.
It was during the exchange that Harry delivered the clear political jab:
“’Folks, it’s Prince Henry Charles Albert David of Wales Sussex. What are you doing here?” Colbert began the sketch.
“’Hold on, I wouldn’t say we’re obsessed with royalty,” Colbert later stated in the sketch.
Harry responded with the line that drew immediate audience reaction: “Really? I heard you elected a king,” which received audible boos from the studio crowd. It was widely interpreted that Harry was delivering a clear nod to the “No Kings” movement, which directly relates to what many critics believe are the authoritarian policies and tendencies espoused by Trump.
