The first royal to really be linked to The Carlyle was Princess Diana. While it’s entirely possible that Charles stayed there during his trips to New York in the ’80s and ’90s, it was the paparazzi-plagued princess who first got photographed outside the hotel in December 1995. She was in town to accept United Cerebral Palsy’s humanitarian award at its black-tie gala. But a few weeks earlier, she’d given an explosive interview in which she’d revealed to BBC reporter Martin Bashir the extent of Charles’s affair with Camilla Parker Bowles. (“There were three of us in this marriage, so it was a bit crowded,” she told Bashir on the BBC news program Panorama.) A 2021 investigation found that Bashir had deceived Charles Spencer, Diana’s brother, in order to gain an introduction to the princess and persuade her to do the tell-all—with Bashir showing Spencer fabricated bank statements that made it seem that people in his and Diana’s circles were getting paid to spy on her for the press. (The BBC subsequently apologized, as did Bashir, though he maintained that the fake bank statements did not impact Diana’s decision to participate in the interview.) Yet at that time, the fervor around Diana’s personal life was at an all-time high. Images of her outside the hotel were splashed across tabloids, with The Carlyle’s distinctive gold revolving door in the background. At the gala, she found a sympathizer in Marla Maples, who was then married to Donald Trump and told the Daily News: “With everybody talking about you, there comes a time when you want to have your say…I wish she could find someone she could trust. Every time she goes to see a psychic or a psychiatrist, they talk about her.”
While in town in the summer of 1995, she had a secret meeting with perhaps the only person who rivaled her in fame: John F. Kennedy Jr. The young Kennedy wanted Diana to pose for the cover of his fledgling magazine, George. Terrified that the news would leak—and the press would descend—he strategized with his assistant, RoseMarie Terenzio, on how to arrive at The Carlyle undetected. “I told John, ‘Don’t go in the side entrance, because if anyone does leak it beforehand, people will expect you to go in the side. So walk in the front door,’” Terenzio writes in her memoir, Fairy Tale Interrupted. She was right: Details of their meeting didn’t leak until decades after both of their deaths. Although that’s arguably not the best story to come out of the days of Diana’s stays: “The most famous elevator ride in history took place in The Carlyle. Because one of the guys that operates the elevator said to me, ‘You know, we once had Princess Diana, Michael Jackson, and Steve Jobs all at the same time.’ Now, that is a power elevator,” Morgan shared in the documentary. “It was completely silent until Diana began singing ‘Beat It.’”
Diana returned in December 1996 for the Costume Institute Benefit at The Metropolitan Museum of Art, and again in June 1997, for a Christie’s auction of her dresses, which, per a Daily News report, raised $5.8 million for charity. When the royal tragically died in a car crash about two months later, The Carlyle flew its flags at half-staff. “She certainly was loved in New York and seemed to respond very well to that,” Dan Camp, the hotel’s then president, told the press. “There was a relaxed way about her being when she was in this city.”