A week ago, biographer Caroline Hallemann noted that there were/are many parallels between Carolyn Bessette and the Duchess of Sussex. Those parallels were backed up by many people who knew Carolyn, like Carole Radziwill, who spoke about how crazy it was for both Carolyn and Meghan to marry into these bonkers dynasties. Well, the royalists at People Magazine were absolutely furious about that story, because that’s the only explanation for this completely bizarre People Magazine cover. They’re comparing Princess Diana and Carolyn Bessette, but also making a larger comparison between the Windsor dynasty and the Kennedy dynasty. I feel like the whole point of this strained reach came towards the tailend of the cover story, when the same biographer, Caroline Hallemann, announces that Prince Harry is “floundering” just like John F. Kennedy Jr, and something something Prince William is the true heir to Camelot! I’m being only slightly hyperbolic. Some excerpts:
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.
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.
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.
One of John [Kennedy Jr]’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.
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.
I don’t understand the need for all of this compare-and-contrast. Yes, both families are dynastic and wealthy. Yes, it would be interesting to talk more about how Carolyn and Diana largely defined the 1990s sartorially and culturally. Yes, there’s real history there, especially given QEII’s jealousy of Jackie Kennedy. But it feels like the whole point of this piece is to say that Harry is “floundering” and that William is embracing his Camelot-like destiny. Don’t believe your lying eyes, I guess.
Photos courtesy of Avalon Red, Backgrid, Cover Images. Cover courtesy of People.
- PRINCESS DIANA OF WALES, LADY DI. 1996 WASHINGTON DC PHOTO WAS ON THE COVER OF US NEWS MAGAZINE AND WAS THE BEST SELLING ISSUE IN 70 YEARS. . LADY DI . PORTRAIT. RETRATO. HEADSHOT,Image: 538725362, License: Rights-managed, Restrictions: World rights – Fee Payable Upon Reproduction – For queries contact Avalon: +44 (0) 20 7421 6000 sales@avalon.red, Model Release: no, Credit line: Look Press Agency/Look Press / Avalon
- Prince Charles, Prince of Wales, and Diana, Princess of Wales, visit Australia Princess Diana in Tasmania The princess is wearing the Spencer family tiara and a dress by Bruce Oldfield. State Reception in Hobart,Image: 549283529, License: Rights-managed, Restrictions: WORLD RIGHTS – Fee Payable Upon Reproduction – For queries contact Photoshot – sales@photoshot.com London: +44 (0) 20 7421 6000 Florida: +1 239 689 1883 Berlin: +49 (0) 30 76 212 251, Model Release: no, Credit line: John Shelley Collection / Avalon
- London, UNITED KINGDOM – **FILE PHOTOS** PRINCESS DIANA pictured in 1990s archive photos Pictured: PRINCESS DIANA BACKGRID USA 4 JULY 1996 BYLINE MUST READ: MediaPunch / BACKGRID USA: +1 310 798 9111 / usasales@backgrid.com UK: +44 208 344 2007 / uksales@backgrid.com *UK Clients – Pictures Containing Children Please Pixelate Face Prior To Publication*
- Palma de Mallorca, SPAIN – Prince William furious after the controversial interview with his mother Lady Diana in 1995. **SHOT ON 08/08/1987** Pictured: Princess Diana BACKGRID USA 25 MAY 2021 BYLINE MUST READ: Best Image / BACKGRID USA: +1 310 798 9111 / usasales@backgrid.com UK: +44 208 344 2007 / uksales@backgrid.com *UK Clients – Pictures Containing Children Please Pixelate Face Prior To Publication*
- Palma de Mallorca, SPAIN – Prince William furious after the controversial interview with his mother Lady Diana in 1995. **SHOT ON 08/08/1987** Pictured: Princess Diana BACKGRID USA 25 MAY 2021 BYLINE MUST READ: Best Image / BACKGRID USA: +1 310 798 9111 / usasales@backgrid.com UK: +44 208 344 2007 / uksales@backgrid.com *UK Clients – Pictures Containing Children Please Pixelate Face Prior To Publication*
- Crown Prince Charles and his wife Princess Diana drive to Prince Andrew’s and Sarah Ferguson’s wedding in an open carriage (23.07.1986). Where: London When: 23 Jul 1986 Credit: Jörg Schmitt/picture-alliance/Cover Images
- JFK JR. PHOTO: KEN KATZ koolphoto@yahoo.com Featuring: John F. Kennedy Jr and Carolyn Bessette When: 01 Jan 1998 Credit: Ken Katz
- , New York, NY – 10/06/1996- JFK Jr. and new wife Carolyn Bessette Kennedy just back from their honeymoon pose for photographers outside their Tribecca home. PHOTO by: Ken Katz/startraksphoto.com -K140002MRMRSJFK96_KK Editorial – Rights Managed Image – Please contact www.startraksphoto.com for licensing fee Startraks Photo New York, NY For licensing please call 212-414-9464 or email sales@startraksphoto.com Startraks Photo reserves the right to pursue unauthorized users of this image. If you violate our intellectual property you may be liable for actual damages, loss of income, and profits you derive from the use of this image, and where appropriate, the cost of collection and/or statutory damages. Featuring: John F. Kennedy Jr and Carolyn Bessette Where: New York, New York, United States When: 01 Jan 1998 Credit: Ken Katz/startraksphoto.com
- New York, N.Y. – 11/17/1998- Carolyn Bessette looking very alone standing on a Tribeca street deep in thought. Exclusive -PHOTO by: Ken Katz/startraksphoto.com -KK_310792 Editorial – Rights Managed Image – Please contact www.startraksphoto.com for licensing fee Startraks Photo New York, NY For licensing please call 212-414-9464 or email sales@startraksphoto.com Startraks Photo reserves the right to pursue unauthorized users of this image. If you violate our intellectual property you may be liable for actual damages, loss of income, and profits you derive from the use of this image, and where appropriate, the cost of collection and/or statutory damages. Featuring: Carolyn Bessette Where: New York, New York, United States When: 01 Jan 1998 Credit: Ken Katz/startraksphoto.com
- JOHN F KENNEDY JR AND CAROLYN BESSETTE STOCK IMAGE. NEW YORK CITY. CIRCA 1990S. PICTURES /
























Obviously in hindsight the parallels are absolutely chilling, but they were very different people with extremely different backgrounds and life experiences.
Exactly
As someone who has exhausted books about dynasties and royalties.
Blonde hair.✔️
Blue eyes. ✔️
Long legs.✔️
However, beyond the superficial, you couldn’t find 2 more different people.
Like, blonde hair dye and press and paparazzi who made their lives miserable?
I don’t mean to exaggerate or to belabor the point, but imagine if these women could have simply utilized public transportation and gone about their daily lives without being harassed — their lives would have been immeasurably different, and one or both of them might still be alive today.
So last week this biographer discussed the similarities bw Meghan and Caroline, with people like Carole Radziwill making the same claim. And this week that whole thread was dropped by the same biographer in People magazine and ends with the conclusion that William is embracing his role and isn’t earthshot wonderful. Not exactly subtle.
Jackie’s observations about the late queen and the whole royal scene were fascinating. First, she was told her sister Lee Radziwill, Carole’s mother in law, would not be invited to the state dinner, whilst she and the President were in London, because Lee had been divorced before marrying the man who was Prince Radziwill. Jackie enlisted the White House Chief of Protocol, with the plea, “Angie, you’ve got to help me.” So the snafu was resolved, then Jackie was asked whom she would like to meet, at the State dinner. She requested Princess Marina and Princess Margaret. Cue the state dinner. As she later recounted to Gore Vidal, who was famously indiscreet about her, having shared a stepfather in Hugh Auchincloss, “No Margaret, no Marina, but every Commonwealth Head of Agriculture you could shake a rake at.” …suffice it to say she was not treated to what we would have termed hospitality. Of the late Queen and Philip, she observed, “one sensed no connection between them.” Of the late Queen herself, she simply recorded, “I think she resented me.” …..sounds pretty much spot-on, and Jackie had a sharp eye.
Diana was far more famous and global phenomenon, and Carolyn was far more private.
Other than getting famous by accident because of who they married, I don’t think there’s much of a similarity.
Today’s celebrities must be really boring, which is why these two women are on thr cover for non-existent similarities (except maybe in the area of paparazzi).
“I don’t understand the need for all of this compare-and-contrast. Yes, both families are dynastic and wealthy.”
It’s because they hate that a Black woman has proximity to the two pretty blonde haired blue eyed women of status. Never mind that the same entities that are heralding these women harassed, stalked and tortured them when they were alive. And Harry has the gall to go to any lengths to protect his Black wife when the two now dead white were not protected by their husbands (it wasn’t intentional on John junior’s part but he did failed his wife)