Trump’s Love Affair With the Royal Family Dates Back to His Mother

The youngest of 10 children, Mr. Trump’s mother sailed to the United States around 1930, reporting to American immigration officials that she had an eighth-grade education. Late in life, she had a taste for luxury, which her son was happy to indulge, said Gwenda Blair, the author of “The Trumps: Three Generations That Built an Empire.”

“The photos that we see of Queen Elizabeth in her dowager clothes, and often, if it is winter, in some extremely luxurious warm fur coat, reminds me of how his mother came across,” she said. Mrs. Trump died, age 88, in 2000.

As a real estate developer and television personality, Mr. Trump seemed to regard the royal family as a benchmark for prestige. In the 1980s, he circulated a rumor that Prince Charles and his wife, Diana, were considering purchasing a unit at Trump Tower, Mr. D’Antonio wrote in his book.

He expressed attraction to Diana, Princess of Wales, sometimes in crude terms.

Selina Scott, a British journalist who interviewed him for a documentary in 1995, recalled that as soon as she entered his office in Trump Tower, “he wanted to know the intimate details of the deteriorating state of the marriage” between Charles and Diana. After the two divorced, in 1996, Ms. Scott later wrote, Mr. Trump sent Diana “massive bouquets of flowers, each worth hundreds of pounds,” accompanied by handwritten notes.

In 1997, shortly after Diana had died in a car accident, Mr. Trump told the television journalist Stone Phillips that he regretted not having asked her on a date. “Do you think you would have seriously had a shot?” Mr. Phillips asked.

“I think so, yeah,” Mr. Trump replied. “I always have a shot.”

Mr. Trump returned to the subject with the radio host Howard Stern, who asked him, “You could have gotten her, right? You could have nailed her?” Mr. Trump joked that he would have asked her to take a medical exam beforehand.