In an excerpt from The Kennedys & the Windsors, read the untold story of the conversation about a magazine cover that never came to be.
An issue of George magazine with Diana on the cover would be guaranteed to sell—both to advertisers and on the newsstand. Not to mention, she fit the ethos of the burgeoning publication.
“It seems obvious why would’ve wanted her on the cover, because he was trying to capture the intersection of political life and celebrity life in his magazine. Lady Di, at that moment, was a perfect example of that because she was a symbol of the intersection of those things. She was a celebrity, a royal who had a defined role, but she also had a personal and political mission. She had ideas about how she wanted to help the world.
She had her own feelings about her service, at least that’s the perspective that I got from her,” John’s close friend artist Sasha Chermayeff, who had known him since his boarding school days, said.
“She was loved by America, too. We loved her, everybody loved her. ” John and Diana were uniquely matched. They were glamorous, beautiful, and charismatic—but there was substance there, too.
They were also both so often underestimated, by the public and the people around them. Editorially, a conversation between them was an interesting prospect.
“He was America’s equivalent of Diana,” said British photographer Platon, who often worked with John at George magazine. “They both had this quiet aura in the media, that they don’t have to ever shout about who they are and what they do. They just give you this shy look, that you are just drawn to it. And you can’t fake that.
That’s not built by marketing companies and PR companies. That’s not a strategy. That’s real. Both had complicated legacies and history that had already passed, even when they were at their prime.
And they didn’t seem to go begging for attention. They knew that they had this quiet power that you can’t cultivate. It’s just there. And I can’t tell you how many celebrities wish they had an ounce of that aura.
” Initially, John sent Diana a letter asking for a meeting, and per her private secretary Patrick Jephson, she was “keen on the idea. ” And so calls were made, and a date was arranged for John to meet with Diana at the Carlyle hotel during her visit to New York in December 1995. She was going to be in the city to receive a humanitarian honor at the annual United Cerebral Palsy Awards gala.
The trip also came one month after Diana’s bombshell interview with Panorama, in which she spoke at length about the failed state of her relationship with Prince Charles.
“We agreed that she would find time in her program in New York to meet him. Nobody wanted it to be public,” Patrick remembered, so the encounter was set for midday, when, in theory, the hotel would be the least busy.
“I always think that people imagine that we have a bat phone on my desk and Diana’s desk and Princess Stephanie’s and we can pick it up and the other will answer,” John once said joking. But while they were hardly confidants, they had met before. About a decade prior, they’d both attended a luncheon at Bunny Mellon’s farm in Virginia during the 1985 royal visit to DC.
“She has the most unusual upwards glance, really seductive,” he said at the time to his friend Billy Noonan, noting that she also had “the most unusual blue eyes. ” But ten years later, this meeting wasn’t a date—or really even a social call. John was there on business. He wanted to ask Princess Diana to pose for the cover of George.
John was excited, but he was also “annoyed about everybody hinting about how this would be a marriage made in heaven if they could be together,” Sasha said.
“The classic, still continued, idea that monarchies must come together for the good of the families. ” And from the very beginning, John expected someone to leak the details of this encounter to the press.
“When you’re talking about people that are that famous, it’s interesting just if they’re spotted on the street,” Richard Johnson, the gossip columnist who edited the New York Post’s Page Six in the 1990s, said. “Photographers will start taking pictures. They don’t have to be doing anything.
” A photo proving a rendezvous between the People’s Princess and America’s Prince in the summer of 1995? That would have been a guaranteed front‑page story. Princess Diana always stayed at the Carlyle. Located on New York’s Upper East Side, the luxurious hotel has an English charm.
And it has long been a royal favorite for visits to New York City. James Sherwin, the manager of the hotel at the time, only added to the appeal. He had at one point worked for Lady Elizabeth Anson, a cousin of Queen Elizabeth’s, and understood Diana’s need for privacy completely, describing the hotel’s discretion as “extraordinary.
” “It was not as big as many of the other New York hotels, so you could control it in a slightly different manner,” he said. John, too, was intimately familiar with the property and its security; he had lived there with his mother and sister in the years following his father’s death.
When they arrived at the Carlyle, John and his executive assistant RoseMarie Terenzio simply walked off Madison Avenue right through the hotel’s front door, unfettered by the crowd of press, who just so happened to be waiting at the other entrance. Patrick was there to meet John in the corridor between the foyer and the bar. It was dark, so from a distance, Patrick didn’t recognize the tall man as he approached, but John immediately extended his hand.
“John Kennedy,” he said, introducing himself despite the fact that everyone in the room—and practically everyone in the world—knew exactly who he was. He always did that.
“He was very, very polite. I would say modest. There was no swagger to him. He was quite right and proper,” Patrick said.
They made their way to the elevator, leaving RoseMarie in the lobby. Princess Diana greeted them in the penthouse suite—much like John, she was dressed smartly.
“It was a working meeting. Business attire,” Patrick said. Once in the room, the pair sat down at a table to talk. Tea was served, or maybe it was champagne—that detail has been lost to history, but regardless of the drinks, John appeared nervous.
“He was quite in awe of her,” Patrick said. “Not uncomfortable, but he certainly seemed to be on his best behavior,” and acutely aware that he was asking Diana for a favor. Diana, on the other hand, was unfazed.
“She was very cool—and jolly, you know, and smiley and welcoming. ” Despite the nerves, John didn’t delay in making his pitch. He perched on the edge of his chair and asked Diana to appear on the cover of George. John had brought along with him several ideas for the cover shoot. His creative director Matt Berman had mocked up sketches of Diana on tracing paper in Magic Marker to show her what the photograph might look like.
One featured her wearing a three‑corner hat like one from the Revolutionary War; another, oddly enough, showed her in the back of a limousine with the window rolled halfway up, in an attempt to avoid photographers. While George was still in its infancy, its visual identity was quickly solidifying. The magazine would become known for having its cover stars dress up as George Washington or other iconic figures from American history.
Barbra Streisand, for example, posed as Betsy Ross; Harrison Ford took on the persona of Abraham Lincoln in his cover shoot; Robert De Niro’s Washington look came complete with a replica of the founding father’s battle sword. Controversially, for an issue pegged to President Bill Clinton’s fiftieth birthday, Drew Barrymore posed on the cover in a slinky nude dress—a not‑so‑subtle nod to Marilyn Monroe’s birthday serenade to President Kennedy.
John’s mindset was “Why is it OK for everyone else to play with the political iconography of my family and I can’t? It’s my family, it’s not offensive to me. Why should it be offensive to you? ” In his editor’s letter for that issue, he wrote simply, “And on our cover, Drew Barrymore reprises what may be the most memorable ‘Happy Birthday’ sung in the history of American politics.
Cheers. ” But unfortunately, this particular conversation about the cover of George was over before it started. Prior to John even opening his mouth to ask about doing an interview and a photo shoot, Diana had already made up her mind to turn down the opportunity. She needed the magazine to be a success before she’d publicly front it—and even with a Kennedy at the helm of the publication, that was hardly a guaranteed prospect.
“Well, you know, this is all very nice, John. Thank you. But I hope you’ll forgive me if I don’t take up the opportunity this time, but would love to maybe for your fiftieth or your hundredth issue or something,” she said. While he was disappointed, John understood that the decision was final, and so conversation quickly turned to other things.
They had both spent time with the Catholic nun Mother Teresa, so they talked about her mission. And part of the reason Diana had taken the meeting in the first place was to ask John about his up-bringing. She wanted to raise Harry and William the way Jackie had raised John and Caroline.
“I’m hoping he’ll grow up to be as smart about it as John Kennedy, Jr.,” Diana would say about her eldest son to journalist Tina Brown years later, weeks before her death. “I want William to be able to handle things as well as John does. ” Diana had long looked up to Jackie and saw parallels between their lives.
She was “very intrigued” by her, Brown’s Vanity Fair successor Graydon Carter said, noting that during a dinner Diana “kept asking questions—she wanted to know how Jackie Kennedy was treated by the Kennedy family because, I think, she felt there were parallels between how Jackie was treated and the way she was treated by the royal family. ” Perhaps less significantly, the appointment with John was also a ploy by Diana to make her sister‑in‑law Sarah, the Duchess of York, jealous.
By this point, Diana and “Fergie,” as she was known, had become rivals of sorts, and the redheaded soon‑to‑be ex‑wife of Prince Andrew apparently had a crush on JFK Jr. “The Princess’s wish to meet America’s most eligible bachelor owed more than a bit to the fact that he was at the time a particular pin‑up of Fergie’s,” Patrick later wrote. Fergie would eventually visit the George offices, mingling and taking pictures with editorial staffers, but it seems unlikely that she met with John.
“It was brief,” RoseMarie said. “I don’t remember exactly how it came about. I think she was doing meetings for Weight Watchers in the city. ” The duchess appeared in the September 1996 issue in a small way.
She was featured in a photo high-lighting her visit at Hale House in New York City, a “facility for drug‑addled and HIV‑positive infants. In the caption, George noted that she was following “her former sister‑in‑law Diana’s benevolent instincts. ” In the end, John and Diana spent “a pleasant enough” hour or so together.
“I remember he felt like it was more fun than he had expected in the royal meeting, a little more genuine,” Sasha said. “I think he liked her, put it that way. ” And despite later rumors that the couple had an affair that was consummated at the Carlyle that day in a “moment of pure lust,” Patrick said he remained in the room the whole time.
“I stayed in the room throughout and was not aware of any mad, passionate activities,” he said. “My observation was, it was a kind of mutual sounding‑out. It was a kind of appraisal, and it wasn’t overtly flirtatious, but it was friendly. ” Prior to the meeting, Patrick and Diana had discussed how long to let the conversation go on.
When it reached that point, Patrick interrupted, apologizing, and saying something like, “We’ve got to get ready for the next thing,” giving the princess an out. As John made his way back downstairs, Diana turned to Patrick and said “words to the effect of ‘That went well, and it was the right thing to do. ’” “I can’t remember the words, but there was a degree of sympathy.
I think she might have spoken about the famous picture of him as a little boy. And she had sympathy for him growing up with the name and being the object of public fascination. These were things that she could relate to. I definitely picked up a sense of sympathy, of concern, for him.
She didn’t see him as the rest of the world saw him. As this big, famous, handsome guy. She saw him, I think, as rather vulnerable because he had grown up in public,” Patrick would later recall. But while the ask to appear on an early cover was denied, John didn’t leave the hotel entirely empty‑handed; Diana wrote him a note, which read, “Thank you so much, but not right now.
” And again she had agreed to consider appearing on a future cover of George, possibly enjoying the tease of being able to say yes in principle, but that they’d have to wait. As John exited the hotel, his assistant asked the obvious question: “Well, how was she? ” “She’s tall, taller than I thought,” he said.
“She’s very nice, shy, a little coy. But she’s not going to do it. ” “I could tell he was disappointed that she said no,” RoseMarie said. And with that, they trekked back to midtown to the George offices.
“What was she like? ” a chorus of editors asked upon their arrival. As he dropped the imagined cover sketches back on Matt Berman’s desk, John said, “Well, she said no, but she had a great pair of legs! ” From there, John kept things light, never lingering on the disappointment.
“At the end of the day, all he cared about was getting a yes to the cover of George,” RoseMarie said. “Everything else was kind of, whatever. ” Cindy Crawford in a midriff‑baring George Washington–meets–pinup girl ensemble was featured on the cover of the debut issue of George, which John revealed at a press conference at Manhattan’s Federal Hall in September 1995.
When the suggestion of Crawford initially came up, John’s future wife, Carolyn Bessette, insisted it was the right call.
“She’s all‑American, a self‑made woman, sexy, strong, and smart,” Carolyn said, in an opinion shaped by her years of work-ing in fashion PR. She was right. The image was instantly iconic, and it set a precedent for the magazine. But despite the inherent Americanness of George, John continued to think about how Princess Diana could be a part of the magazine, and she was still mentioned within its pages quite often.
In the August 1997 issue, for example, Marla Maples appeared on its signature “If I Were President” page, answering the question “What foreign problem would you like to solve? ” with “Princess Di’s peace of mind. ” The September 1997 issue, which went to print a few weeks before Diana’s untimely death, included a photo of her alongside Elizabeth Dole at a Red Cross event for land mine survivors.
The two women were also pictured together in the final issue John edited. John never gave up on the idea of putting a British royal on his cover. He stayed in touch with Diana, asking her for an interview more than once. In February 1997, she penned him a letter, thanking John for sending her issues of the magazine, but once again, she had to “regrettably” turn down his offer.
But it wasn’t an outright refusal. Once again, she suggested that she’d be in touch when a conversation might be appropriate. She finished off the note by writing, “I hope”—with “hope” underlined—“the media are leaving both you and Carolyn alone. I know how difficult it is, but believe it or not, the worst paparazzi are here in Europe!
” “I think she saw in him a fellow victim, if you can put it that way, of life in the public eye and difficulty of knowing who to trust,” Patrick said.
“And I think that that did create a connection between them. I wouldn’t call it a bond, but an affinity, a recognition of each other’s unusual hardships and difficulties. ” John was also interested in pursuing Prince Charles for George.
According to society columnist Aileen Mehle , in 1998 John and his wife, Carolyn, attended a private dinner thrown by Charles at Kensington Palace, during which John asked the Prince of Wales to appear on the cover of George to mark Charles’s fiftieth birthday in November of that year. A photo of the Prince of Wales had appeared within the pages of George before; a 1997 issue notably featured the iconic image of Charles meeting the Spice Girls.
But like his ex, Charles was hesitant to collaborate with Kennedy, and once again, John was turned down by the House of Windsor. To appear on the cover of a magazine or a tabloid via a licensed photo was one thing; to pose for a cover shoot and presumably consent to an interview with John was another. Per Mehle, the request was “graciously met by something that sounded like ‘um, uhm, hum, we’ll see, um, uhm, hum.
’ After all these years, is an expert at avoiding the pinning-down process. ” George did eventually reach its fiftieth issue before closing in 2001, but it never had a royal cover star. Tragically, by the time the magazine printed its final edition, both Diana and John were dead.
From The Kennedy and the Windsors: The Story of Two Dynasties, One Born, One Made by Caroline Hallemann, to be published on June 2, 2026, by G. P. Putnam’s Sons, an imprint of Penguin Publishing Group, a division of Penguin Random House LLC. Copyright 2026 by Caroline Hallemann.
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