Princess Diana and Carolyn Bessette Kennedy Had More in Common Than Anyone Realized (Exclusive)

This week's PEOPLE cover story goes inside the surprising moments and shared struggles that unite the Kennedys and the Windsors

NEED TO KNOW

• In this week’s PEOPLE cover story, the surprising parallels between Princess Diana and Carolyn Bessette Kennedy
• How Jackie Kennedy and Queen Elizabeth navigated extraordinary fame — and found common ground
• What John F. Kennedy Jr., Prince William and Prince Harry shared about grieving in public

They came from different countries, different worlds and different dynasties. Yet Princess Diana and Carolyn Bessette Kennedy shared an experience few people could understand: living under the glare of relentless public fascination.

In the 1990s they became two of the most photographed women in the world. Their marriages fueled endless speculation. Their clothes inspired imitators. Their every move made headlines. And when both women died tragically young, the world responded in remarkably similar ways: mountains of flowers, wall-to-wall coverage and a sense that something larger than a celebrity had been lost. But Diana and Carolyn were one chapter in a much longer story. 

For decades the Kennedys—often described as America’s closest thing to royalty—and the Windsors have captivated the world through a mix of glamour, triumph, scandal and heartbreak. Jackie Kennedy and Queen Elizabeth would come to define the ties between the two families. In the early ’60s, one was a young First Lady helping to usher in a new era of American optimism. The other was a young monarch carrying the weight of a centuries-old institution.

“They had great proximity to power and soft diplomacy but not true political power behind them,” author Caroline Hallemann, whose new book The Kennedys & the Windsors explores the surprising intersections between the most famous political dynasty in the U.S. and Britain’s royal family, tells PEOPLE in this week’s cover story.

Yet both wielded enormous influence, balancing motherhood with life in the public eye as they became enduring symbols of their countries.

By the time Jackie arrived at Buckingham Palace for her first meeting with Queen Elizabeth in June 1961, she had long been fascinated by royalty. Years earlier, as a budding reporter, she had even slipped into a Washington press reception attended by the then-Princess Elizabeth.

The relationship that followed would become one of mutual respect and understanding. In the Queen, Jackie found someone who understood the unique pressures of public life. In one conversation, Elizabeth offered advice that would resonate throughout both women’s lives. Her guidance, Hallemann says, was to learn to “dole out your energy and take care of yourself when you’re on this public stage.”

Decades later another pair of women would find themselves linked by the spotlight. While Jackie and the Queen learned to manage public attention, Diana and Carolyn struggled with the costs of it. 

Diana was born into the British aristocracy before marrying Prince Charles. Carolyn built a career as a New York fashion publicist before falling in love with John F. Kennedy Jr. Both faced extraordinary scrutiny. 

“It was difficult to join these families,” Hallemann says. “There were rules and expectations coming from within the family—and from the outside world.”

How she juggled the demands of public life with family responsibilities was something that had long intrigued Diana about Jackie Kennedy. Hallemann says the princess viewed Jackie as “a real role model” for the way she navigated enormous fame while raising her children.

Related: Did Carolyn Bessette Kennedy and Princess Diana Really Cross Paths Weeks Before Diana’s Death?

Despite her struggles with the press, Diana eventually learned to harness media attention in service of causes she cared about. Carolyn struggled to find that balance.

“She was completely overwhelmed and never found a way to deal with it,” Hallemann says. 

Yet both women ultimately became more than famous wives, defining the style and cultural ideals of their generation.

“They both understood the power of clothing to make a statement,” says Pamela Keogh, author of Jackie Style.

For Diana, that influence sometimes created tension. “It caused problems in her marriage because she definitely pulled focus from Charles,” says Keogh. “He knew it and didn’t like it.” John, by contrast, “liked it when Carolyn got all the attention,” she adds. “And that speaks to his self-confidence.”

When Diana died at 36 in a Paris car crash while being pursued by paparazzi on Aug. 31, 1997, the tragedy struck close to home for Carolyn.  “She was worried that it was going to happen to her,” says Hallemann. 

Less than two years later Carolyn, 33, and John, 38, died in a plane crash. By the summer of 1999 three of the decade’s most recognizable figures were gone.

The losses highlighted one of the most unusual burdens shared by the Kennedys and the Windsors: grieving in public. Few images are more enduring than 3-year-old John saluting his father’s coffin. More than three decades later another image would become etched into the collective memory: Prince William and Prince Harry—just 15 and 12—walking behind their mother’s coffin through the streets of London.

“Your heart can’t fail to break,” says Diana’s former private secretary Patrick Jephson.

One of John’s friends told Hallemann that while John barely remembered his father’s funeral, he struggled with the public expectations surrounding his mother’s death in 1994.

“He felt he had to play a role for the press and the public when Jackie died,” Hallemann says. “What he really wanted was to escape and be around the people who truly knew her.”

William and Harry have expressed similar feelings, with Harry writing in Spare of his confusion at witnessing strangers mourn a mother they had never met.

The cycle continues. When Queen Elizabeth died in 2022, Prince George, 12, and Princess Charlotte, 11, joined the royals before a worldwide audience. More recently Kennedy family members were photographed mourning Caroline Kennedy’s daughter Tatiana Schlossberg after her death from cancer in late 2025 at the age of 35. 

“People expect to see this grief play out,” says Hallemann. “There’s a relationship there in times of tragedy.”

Grief was only part of the inheritance. For all their privilege, John, William and Harry entered adulthood saddled with expectations few could imagine.

“They were charismatic figures,” says Keogh. “They were like rock stars. Young women dreamed of marrying a prince or JFK Jr.”

Yet fame offered no clear road map. John sought to carve out an identity with George magazine. Decades later Prince Harry would pursue a different kind of independence, stepping away from royal duties with his wife, Meghan Markle, and building a new life in California.

“They were trying to forge their own path outside of their families’ legacies,” says Hallemann. “But they both floundered.”

Meanwhile, William increasingly embraces the role that awaits him, defining himself through initiatives such as the Earthshot Prize. In 2022, when his environmental global challenge came to Boston for an awards ceremony to honor people who are working on eco-solutions to repair Earth, the future King was welcomed by Caroline Kennedy and her children Tatiana and Jack Schlossberg, 33.

The connection was fitting: Inspired by President Kennedy’s ambitious Moonshot challenge, Earthshot reflects the same belief that bold ideas can rally people around a common purpose.

Nearly six decades after Jackie found common ground with Queen Elizabeth, a Kennedy and a royal found themselves together once again. And they remain as culturally potent as ever. FX recently revisited the romance of John and Carolyn in the hit series Love Story, while Netflix is filming a Kennedy drama widely seen as a potential American counterpart to The Crown.

Can't get enough of PEOPLE's Royals coverage? Sign up for our free Royals newsletter to get the latest updates on Kate Middleton, Meghan Markle and more!

“Hollywood keeps this idea of them being America’s First Family alive as well,” Hallemann says.

Perhaps that’s because, for all their glamour and privilege, both families have lived out life’s most universal experiences—love, loss and resilience—on the world’s biggest stage.

Read the full article here