When President Donald J. Trump visited Britain in 2019, British officials arranged for him to have afternoon tea with Charles, then the Prince of Wales, at his London residence, Clarence House. The thinking among British diplomats was that the 70-something heir to the throne would be a good partner for the 70-something heir to a real estate fortune.
It was not clear that Mr. Trump, now 78, and Charles, now 76, had much in common, beyond age and inherited wealth.
But the British were on to something in trying to deepen the personal ties between Mr. Trump and the royal family. He already regarded Queen Elizabeth II, the king’s mother, with a reverence bordering on awe. His visit to Buckingham Palace ranked as one of the highlights of his first term.
With the Trump restoration imminent and the British government now led by a left-of-center prime minister, Keir Starmer, who could find himself politically at odds with Mr. Trump, the crown may end up being a useful weapon in Britain’s campaign to keep the president-elect’s affections.
On Saturday, Mr. Trump forged ties to the next generation, meeting Prince William, the 42-year-old son of King Charles III, after both attended the reopening of Notre-Dame Cathedral in Paris. His comments afterward left little doubt that Mr. Trump savors his exposure to royals of any age.
“I had a great talk with the prince,” Mr. Trump told The New York Post. “He’s a good-looking guy,” the president-elect went on. “He looked really, very handsome last night. Some people look better in person? He looked great. He looked really nice, and I told him that.”
Beyond the gushing tone, Mr. Trump raised the eyebrows of royal watchers when he appeared to share details about the health of William’s father and his wife, Catherine, Princess of Wales, both of whom were diagnosed with cancer this year.
Mr. Trump passed along William’s assurance that Catherine was “doing well,” but added, “I asked him about his father and his father is fighting very hard, and he loves his father and he loves his wife, so it was sad.”
Some interpreted his reference to the king as ominous, while others brushed it off as an innocent case of oversharing by Mr. Trump. Buckingham Palace and Kensington Palace, where William has his office, declined to comment on the remarks or on the health of Charles.
Either way, Mr. Trump’s affection for the Windsors is palpable. Diplomats and historians said they could imagine Charles being an emollient presence if Mr. Starmer proceeds with his plan to draw Britain closer to the European Union — something Mr. Trump vehemently discouraged in his first term.
“Britain’s relationship could become much more strained with the United States,” said Ed Owens, a royal historian. “You could see them using the monarchy strategically to maintain as warm relations as possible while continuing the process of rehabilitating the relationship with Europe.”
Although the king studiously avoids politics, Charles has a long-established interest in subjects like the environment. In arranging the afternoon tea in 2019, which included Mr. Trump’s wife, Melania Trump, and Charles’s wife, Camilla, officials said they hoped Charles might gently broach the subject of climate change, on which he and Mr. Trump have starkly different views.
The king “enjoys substantive conversation more than banal platitudes, so there may be scope for him to build a substantive relationship with the president-elect,” said Peter Westmacott, a former British ambassador to Washington who once served as deputy private secretary to Charles.
“With members of the Labour government scrambling to disavow some of the less obliging things they had to say about Trump before he was re-elected, that could be of real value to the U.K.,” Mr. Westmacott added.
Mr. Starmer’s foreign secretary, David Lammy, once described Mr. Trump as “a woman-hating, neo-Nazi-sympathizing sociopath” when he was a Labour backbencher in Parliament in 2018. He has since dismissed those comments as “old news,” and told the BBC that they did not come up when he and Mr. Starmer met Mr. Trump for dinner in Trump Tower in September.
British diplomats said the evening went well, but there is a deep disquiet in London about Mr. Trump’s plans to impose tariffs on trading partners and withdraw support for Ukraine in its war against Russia, not to mention his suspicion of NATO and hostility for the Paris climate accord.
Some cautioned that Charles, for all his well-honed diplomacy, will not budge Mr. Trump from these positions.
“It’s a useful piece of soft power, but up to a point,” said Kim Darroch, who served as ambassador to Washington during Mr. Trump’s first term. “I’m not sure you’re going to get any big concessions from him because he likes the royal family.”
Sally Bedell Smith, who has written several biographies of the royal family, noted that Mr. Trump had encountered Charles before. He played host to him at Mar-a-Lago, his Florida estate, during a visit in 1988, when the prince played polo. And Mr. Trump’s younger brother, Robert Trump, who died in 2020, was a major benefactor of the prince’s philanthropies.
Ms. Bedell Smith said Charles and Mr. Trump had moved in some of the same rarefied circles, including among the royal families of Saudi Arabia and the United Arab Emirates, which could play into the president’s geopolitical agenda.
“Trump is portraying himself as a peacemaker, and Charles has great relations with all those Gulf leaders,” she noted.
Mr. Trump’s fascination with the queen was deeper, dating back to his childhood. He often invoked his mother, Mary Anne Macleod, who was born in Scotland, and how much she admired Elizabeth, according to former aides.
Fiona Hill, a British-born American who served on the National Security Council during Mr. Trump’s first term, said that he dropped hints about a visit to Britain in meetings with Theresa May, who was prime minister at the time. Mrs. May would “pretend not to understand,” reflecting her qualms at playing host to a man who was deeply unpopular with the British public.
“Meeting Queen Elizabeth II was particularly important to President Trump,” Ms. Hill wrote in her memoir. “A meeting with the Queen of England was the ultimate sign that he, Trump, had made it in life.”
His fascination was vividly demonstrated in footage shot during his re-election campaign for a TV series about Mr. Trump’s comeback, “The Art of the Surge.” In it, he showed off a book of photographs of him with the queen (“who was fantastic, by the way”) and Charles, standing near the honor guard at Buckingham Palace.
“Look, Charles, so beautiful,” Mr. Trump said, leafing through the pages. “These images, I mean, who has images like these?”
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