John F. Kennedy Jr.’s Friend Compares Carolyn Bessette to Princess Diana Over Paparazzi Intrusion

A new documentary about John F. Kennedy Jr. explored comparisons between his late wife, Carolyn Bessette-Kennedy, and Princess Diana.

Several of John’s close friends — including his George Magazine colleague Gary Ginsberg and RHONY alum Carole Radziwill — addressed the near-constant intrusion in his and Carolyn’s life from the paparazzi in the three-episode CNN docuseries American Prince. The documentary matched up archival footage of John and Carolyn trying to avoid photographers with similar paparazzi confrontations that Princess Diana endured in the same period.

“Princess Diana was living that struggle [with the paparazzi] so publicly, her fights with the paparazzi during that period [were notorious],” Ginsberg, 62, recalled. “I’m sure Carolyn was watching it and feeling like she was the American version of it. It probably just increased her sense of isolation and frustration.”

Royal biographer Tina Brown suggested that Princess Diana and Carolyn lived “very, very similar lives” because they essentially had no privacy.

“The actual reality of living [with the media firestorm] was something that came with so much pressure and so much ugliness,” Brown, 71, acknowledged.

As Brown revealed in American Prince, the connection between Britain’s actual royal family and America’s unofficial royals, the Kennedys, were acknowledged by both sides.

“[John] was like the number one pinup of the world and, I guess, only Princess Diana comes close in terms of the star power that he carried around,” Brown argued. “I remember when I had lunch with Princess Diana, and she said, ‘I’m hoping that [Prince] William can turn out to be as smart about the press as John Kennedy Jr.’”

The journalist continued, “Diana understood that there was no shucking off of the responsibility. They were the most famous people in the world, so there was very much a parallel.”

Princess Diana and her boyfriend, Dodi Fayed, were killed in August 1997 when their driver crashed while trying to escape the paparazzi through the streets of Paris. In American Prince, Carole Radziwill — who was married to John’s first cousin Anthony Radziwill — remembered how her close friend Caroline responded to Princess Diana’s death.

“It was very profound,” Carole said. “I mean, Princess Diana, she was our age, pretty much. The underlying way in which she died, which was being literally hounded to death by paparazzi. That lesson was definitely not lost on Carolyn.”

The 2024 book Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy included the revelation that Carolyn wanted John to reach out to Princes William and Harry after their mother’s 1997 death, but he was hesitant to do so. Author Elizabeth Beller claimed that John was reluctant to make contact because “he didn’t know them and thought that their situations greatly differed,” which caused a temporary rift in his and Carolyn’s marriage.

Much like Princess Diana, John and Carolyn met a tragic end that sent the entire world into mourning. John was piloting a private plane, with Carolyn and her sister Lauren Bessette on board, en route to Martha’s Vineyard in July 1999 to attend his cousin Rory Kennedy’s wedding when the aircraft crashed shortly before its scheduled landing. John and both Bessette sisters were pronounced dead by crash investigators the following day.

The CNN documentary series offered unprecedented access into John’s life and his struggles with the Kennedy family’s indelible legacy in American politics. Robert De Niro, Cindy Crawford and former MTV News anchor Tabitha Soren were among the contributors who offered personal recollections of John in American Prince.

American Prince premieres on CNN Saturday, August 9, at 9 p.m. ET, with new episodes continuing each Saturday through August 23.