The Kennedys and the Windsors: 11 ways you might’ve not known the families are connected

Marina WattsTue, June 2, 2026 at 11:00 AM UTC

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Prince Philip, Jackie Kennedy, Queen Elizabeth II, and John Kennedy at Buckingham Palace in 1961
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The Kennedy family and the British royal family are intertwined in several ways.

Between state visits, shared interests, and becoming accidental leaders, the Kennedys and Windsors have shaped history and pop culture.

The Kennedys and the Windsors: The Story of Two Dynasties, One Born, One Made is available for purchase wherever books are sold.

Two households, alike in dynasty, is one way to describe the Kennedys and the Windsors.

In Caroline Hallemann's new book, The Kennedys and the Windsors: The Story of Two Dynasties, One Born, One Made, the lives of the royal family and the closest thing the U.S. has to a royal family are intricately connected for almost 100 years. It dates back to Joe Kennedy, the patriarch, becoming the ambassador to England in 1938. This thrust the two families into the spotlight together for generations to come.

President John F. Kennedy and Jackie Kennedy would famously visit Buckingham Palace in 1961, meeting with Queen Elizabeth II and Prince Philip. Following JFK's assassination, the Windsors dedicated a memorial to him at Runnymede. Decades later, JFK Jr. and Princess Dianamet at the Carlyle Hotel in New York City to discuss a George magazine cover. The publication would outlive both of them.

Fast-forward to 2022: Prince William united with Caroline Kennedy in Boston to celebrate the Earthshot Prize, awarded for championing environmentalism and seeking solutions for climate change. Meghan Markle also once said that her favorite celebrity wedding dress was that of Carolyn Bessette's.

Keep reading to find out the 11 ways the Kennedys and Windsors were connected.

Joe Kennedy was the U.S. ambassador to Great Britain

Joseph Kennedy and Winston Churchill in London in 1940
Credit: Keystone/Hulton Archive/Getty

In 1938, Joe Kennedy was sworn in as the U.S. ambassador to Great Britain. He saw the position as an opportunity to advance his career and serve as a springboard for his children to have their own careers in public service.

"If status for his family was what he was seeking, he would have been hard-pressed to pick a better position," Hallemann writes. "The list of ambassadors up to that point included many successful politicians, including five future presidents (John Adams, James Monroe, John Quincy Adams, Martin Van Buren, and James Buchanan) as well as numerous notable businessmen."

As the ambassador, Joe also "planted the seed" to the King of England's secretary, suggesting a state visit across the pond. The following year, King George VI and Queen Elizabeth traveled to New York and Washington, D.C., marking the first time a reigning British monarch would visit the U.S., which would be the first of many.

Jackie Kennedy covered Queen Elizabeth’s coronation

Queen Elizabeth II and Prince Philip at Buckingham Palace in June 1953
Credit: Keystone/Hulton Archive/Getty

While she was being courted by John Kennedy, Jackie was assigned to cover Queen Elizabeth's coronation by The Washington Times-Herald. She reported on the excitement from the streets, speaking with locals to write several features along with her Inquiring Camera Girl column.

During the rainy coronation day in June 1953, “Even with all her connections, both personal and professional, she couldn’t secure a seat inside Westminster Abbey for the ceremony, so instead, she watched the Queen’s grand carriage roll by from a perch outside a Burberry raincoat store," Hallemann writes.

Jackie also took note of the fascination Americans had with the queen. “I’ve noticed how the English newspapers play up everything the Queen does,” a man from St. Louis told Jackie that day. “I suppose she’s the symbol of state to them, but if I were living in a fishbowl like that, I’d jump into the North Sea.”

In less than a decade, Jackie would also be launched into the national spotlight as the first lady.

Accidental leaders

Queen Elizabeth II and John F Kennedy at Buckingham Palace in June 1961
Credit: Getty

Hallemann points out that neither Queen Elizabeth II nor John Kennedy were meant to become leaders. Queen Elizabeth's uncle Edward VIII abdicated the throne within a year of his ascension in order to marry a two-time divorcée, Wallis Simpson. His brother, Elizabeth's father, became King George VI in 1936 and remained so until his death in 1952. As heir to the throne, Elizabeth ultimately took on a role she wasn't born for.

John, meanwhile, hadn't been picked by his father to become president. After Joe P. Kennedy Jr. died in 1944 during World War II, John was groomed to take his brother's place, eventually leading the U.S. “Now the burden falls to me,” John prophesied in what would fulfill itself as the Kennedy curse. “Just as I went into politics because Joe died, if anything happened to me tomorrow, my brother Bobby would run for my seat in the Senate. And if Bobby died Teddy would take over for him."

"They became two of the most significant cultural figures of the last hundred years in the Western world," Hallemann writes. "Both Jack and Elizabeth were bound by familial obligation, but of two very different varieties.”

Parallels between Lee Radziwill and Princess Margaret

Lee Radziwill; Princess Margaret
Credit: Bettmann Archive/Getty; Cecil Beaton/Conde Nast via Getty

Princess Margaret, Queen Elizabeth's sister, along with Jackie Kennedy's sister, Lee Radziwill, had many similarities as the younger sister of the woman in charge, causing a potential sibling rivalry.

After Elizabeth became queen, Margaret still had the perks of being a royal, including "gowns and the invitations to exclusive events, as well as the public scrutiny, but without the explicit purpose of being head of state," per Hallemann. However, it was the lack of education compared to her sister that bothered her.

Meanwhile, Lee's second husband was Prince Stanisław, of the Polish-Lithuanian house of Radziwill, making her essentially royalty.

Margaret and Lee crossed paths a number of times, despite Margaret not being present for the Kennedys' state visit in 1961. Hallemann notes that they were both "at a 1982 party at the Houston home of socialite Lynn Wyatt, for example, and a rare holiday at the Radziwills’ country estate, Turville Grange in Buckinghamshire."

"They were friendly if not friends, perhaps joined together by the all-too-familiar feeling of what a charmed life, albeit two steps behind one’s sister, could feel like," she adds.

Prince Philip attended the funeral for JFK

After JFK was assassinated in 1963, Prince Philip traveled to Washington, D.C., for the funeral since Queen Elizabeth was pregnant and unable to travel. Philip was accompanied by Prime Minister Alec and Elizabeth Douglas- Home, Harold Wilson (the leader of the opposition party), Lord Andrew Cavendish (Kick Kennedy’s brother-in-law), and his wife, Deborah.

At the funeral mass, which was invitation-only, Philip sat far back in the packed church, which only held 1,100. It was only after the service, however, that Philip was able to speak with Jackie Kennedy during an event for diplomats at the White House. At one point, after she became emotional after the draining day, she stumbled into Philip, who was playing with a young JFK Jr.

"Ducking into her husband’s bedroom for a moment alone to compose herself, [Jackie] was surprised and a little embarrassed to find her son playing with Prince Philip on the floor," writes Hallemann. "Philip, blushing, immediately shared that John Jr. reminded him of his own son."

“For a moment, I was unable to place the face—and anyway, I was more concerned with taking John in hand,” Jacie would later say of their interaction, calling Philip a “kind-looking man."

"It was only after another dozen steps that I suddenly remembered that lean, suntanned face. It was Prince Philip! Horrified at the way I had spoken so casually, I turned round to make some apology— but he had gone."

Runnymede memorial

Queen Elizabeth II, JFK Jr., Jackie Kennedy, Caroline Kennedy, Bobby Kenned and Ted Kennedy in Runnymede, England in 1965
Credit: Harry Thompson/Evening Standard/Hulton Archive/Getty

Two years after JFK died, the royal family dedicated a memorial to the late president on an acre of soil in Surrey. Queen Elizabeth dedicated the "symbolic spoil" where King John signed the Magna Carta in 1215 to the American people to honor the late president. The memorial is made up of a garden with 50 granite steps leading to a massive tablet carved with a portion of his inauguration address from 1961.

“Let every nation know whether it wishes us well or ill that we shall pay any price, bear any burden, meet any hardship, support any friend, or oppose any foe in order to assure the survival and success of liberty," reads the Runnymede memorial

"This acre of English soil is now bequeathed in perpetuity to the American people in memory of President John Fitzgerald Kennedy, who in death my people still mourn and whom in life they loved and admired," the queen said at the dedication in May 1965.

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Hallemann writes that the Queen might have came up with the Runnymede memorial on her own. "It has never been officially confirmed by Buckingham Palace, but the idea for the monument is believed by historians to have come from Queen Elizabeth herself."

On the 50th anniversary of JFK's death, his granddaughter Tatiana Schlossberg spoke at the ceremony to commemorate the milestone. “Fifty years after his death, as my grandfather’s story begins to belong more and more to history, I can think of no better place to honor him, to tell and remember his story, and to look again, as he would have wanted us to, towards the future," she said.

JFK Jr. and Princess Diana's NYC meeting

John F. Kennedy Jr.; Princess Diana
Credit: Brownie Harris/Corbis via Getty; Anwar Hussein/WireImage

In 1995, after launching George magazine, John F. Kennedy Jr. arranged for a meeting with Princess Diana at the Carlyle Hotel in New York to discuss her potentially appearing on the cover of an upcoming edition. She politely declined, but JFK Jr. pitched her several times after. Initially, she was "keen on the idea."

JFK Jr.'s friend, artist Sasha Chermayeff, believed he picked the royal for the cover because "he was trying to capture the intersection of political life and celebrity life in his magazine."

"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," Chermayeff added.

However, "this particular conversation about the cover of George was over before it started," Hallemann writes, noting that Diana had already made up her mind to decline the offer before the meeting even started. "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."

After their 1995 meeting, Diana's private secretary, Patrick Jephson, said he believed Diana "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," according to Hallemann's book. "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.”

How George magazine covered Princess Diana’s death

Princess Diana in 1985
Credit: Tim Graham Photo Library via Getty

JFK Jr. was initially hesitant to cover Princess Diana's tragic death in his magazine. The princess died in August 1997 from injuries she suffered in a car crash when involved in a high-speed chase with the paparazzi. She was pronounced dead hours later at the Pitié-Salpêtrière Hospital. Diana was only 36.

"He was not only personally rattled but also felt that anything the magazine did would be seen as a statement about his relationship to the paparazzi—and his wife’s," per Hallemann, referring to Carolyn Bessette.

RoseMarie Terenzio, JFK Jr.'s assistant, revealed that George's creative director, Matt Berman, came up with the concept for the tribute they would eventually run. “Because John didn’t want to do anything about it, Matt came up with this idea to have a photographer go and photograph all of the flowers and all of the tributes in front of Buckingham Palace instead of doing an image of her, because I think he felt like everybody’s going to do that," said Terenzio.

Berman, meanwhile, said they were trying to find their own way to "illustrate" the "enormous story."

“And so the idea was for him to go and just give on-the-streets reportage of what the feelings were and what the grieving looked like. So instead of us publishing historical pictures of her, it was a nice way to show a sensitive take on that moment in time by showing the people who loved her, documented."

George ran a poignant photo essay called "The Lady Vanishes: The People’s Funeral for Diana, Princess of Wales," filled with pictures of the public mourning the People's Princess.

Eerie connection between Diana and JFK Jr.’s deaths

A haunting similarity between Princess Diana's and JFK Jr.'s deaths in 1997 and 1999, respectively, is what they were doing when they died. "In the end, there was a cruel parallel between what killed the People’s Princess and how John and Carolyn died: all three of them were pursuing privacy," Hallemann points out.

JFK Jr.'s friend, Sasha Chermayeff, reflected on the connection: “Like Diana’s death, John’s death, Carolyn’s, and Lauren’s were all related to the same exact thing, which is getting away from the press. . . . I also think the overbearing obligation of showing the right face for the media was driving the escape from public scrutiny,” she said.

Chermayeff added that they both faced "constant pressure from tabloids," resulting in them perpetually "scrambling for privacy."

"They might still be alive if they hadn’t been under pressure to always appear a certain way—for their families, for the countries that they represented in a public manor. . . . It was all related to the same exact thing, which is getting away from the press and showing the right face for the press."

The night of her death, the car Diana was in was evading the paparazzi in a high-speed chase.

JFK Jr., meanwhile, had piloted a small plane carrying his wife, Carolyn Bessette, and her sister Lauren Bessette from New Jersey to Massachusetts that evening. JFK Jr. was going to drop Lauren off in Martha's Vineyard before he and his wife continued to Cape Cod, where they were planning to attend cousin Rory Kennedy's wedding. The plane crashed off the coast of Martha's Vineyard, killing them on impact.

Meghan Markle’s favorite celebrity wedding dress

Meghan Markle and Prince Harry at Windsor Castle in May 2018
Credit: Steve Parsons - WPA Pool/Getty

After Prince Harry and Meghan Markle announced their engagement, there was much speculation about what wedding dress she would wear. “Classic and simple is the name of the game, perhaps with a modern twist. I personally prefer wedding dresses that are whimsical or subtly romantic," she told Glamour at the time about what her style was.

When asked about her favorite celebrity wedding dress, she didn't hesitate with her answer: “Carolyn Bessette Kennedy." She called the silk crepe slip dress designed by Narciso Rodriguez “everything goals.”

Hallemann writes that Markle's Stella McCartney evening reception dress "evoked the essence of Carolyn’s sleek and sexy bridal look." The Suits actress also paid tribute to Princess Diana, wearing an aquamarine ring that once belonged to her.

Moonshot and Earthshot

Caroline Kennedy, Prince William, Jack Schlossberg and Tatiana Schlossberg in Boston in December 2022
Credit: Ian Vogler - Pool/Getty

Prince William and Caroline Kennedy uniting for the Earthshot Prize represented the next generation of Kennedys and Windsors working together. The Earthshot name, thought of by Prince William, was inspired by JFK Jr.'s Moonshot speech and the goal of putting humans on the moon by 1970 (which was accomplished in 1969). Its goal was to repair the planet by 2030.

Caroline called it a "great tribute" to her father and partnered with Prince William and the Earthshot Prize on the initiative. The JFK Library Foundation hosted the 2022 awards ceremony in Boston.

“This collaboration between William and Caroline was more than just another coming- together of the Windsor and Kennedy dynasties; it was the meeting of those who are tasked with carrying these families’ legacies into the twenty-first century," Hallemann writes.

"While Caroline has numerous cousins who bear the Kennedy name, as the only living child of JFK and Jackie, she’s the keeper of the flame, so to speak. As his generation’s heir to the throne, Prince William holds a similar if even more defined role within his own family.”

'The Kennedys and the Windsors: The Story of Two Dynasties, One Born, One Made'
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The Kennedys and the Windsors: The Story of Two Dynasties, One Born, One Madeis available for purchase wherever books are sold.

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