John F. Kennedy Jr. and Carolyn Bessette’s Inner Circle Share Insight Into Their Tumultuous Relationship

They were blissfully happy. Descending the wooden steps of the tiny First African Baptist Church on Georgia’s Cumberland Island, John F. Kennedy Jr. couldn’t take his eyes off his new wife. He and Carolyn Bessette, dazzling in a slinky bias-cut Narciso Rodriguez slip dress, “came out of the chapel and John reached, as a prince would, for the hand of his bride and brought it to his lips and kissed [it],” Denis Reggie, the brother-in-law of the late Senator Ted Kennedy — and the only photographer on the September 1996 wedding’s 35-member guest list — recalled to Today more than two decades later. As Denis captured the moment, “there was a magic there,” he remembered. “You can see [it] in Carolyn’s face, surprise and elation and love and romance and all those wonderful things.”

Less than three years later, that hopeful beginning ended in tragedy. On July 16, 1999, the Piper Saratoga plane 38-year-old JFK Jr. was piloting plummeted into the Atlantic Ocean off the coast of Massachusetts’ Martha’s Vineyard, instantly killing him, Carolyn, 33, and her sister, Lauren Bessette, 34. Investigators determined the son of the late President John F. Kennedy and Jacqueline Kennedy Onassis — who many will forever remember as John-John, the little boy saluting his assassinated father’s coffin — suffered from spatial disorientation on the foggy night en route to cousin Rory Kennedy’s wedding.

Now, nearly 26 years after their deaths, curiosity endures about the dynamics of John and Carolyn’s relationship. From all accounts, the romance that captured headlines was unraveling amid drug use and rumored infidelity. “They were both very passionate,” historian Steven M. Gillon, who wrote 2019’s America’s Reluctant Prince about his friend of 18 years, told one outlet in 2019, though he also admitted that at one point, John “told a friend that he was going to separate from Carolyn, letting her know how serious things were and that they needed to make changes.”

Final Days

The lawyer and the style icon were struggling before that fateful plane ride. The summer of 1999 marked a stressful time for the pair. John’s cousin Anthony Radziwill, who served as best man at his wedding, was in the final weeks of a cancer battle. John was searching for new sources of financing to keep his buzzed-about but bleeding-money political magazine, George, afloat. Carolyn was continuing to grapple with life in the spotlight. And they were fighting.

In March 1999, John joined his wife, who’d already been seeing a psychiatrist, in marriage counseling, journalist Edward Klein revealed in his 2003 book The Kennedy Curse. By that July, however, they hit a new low. The former Calvin Klein fashion publicist “stormed out of the marriage counselor’s office when the therapist raised the subject of her drug use,” which included her “frequent use of cocaine,” Klein wrote. Carolyn began sleeping in a spare room in their NYC apartment, which led John to check into the Stanhope Hotel, where he confessed to one of his closest friends, “It’s all falling apart,” Klein reported.

The couple’s friend Sasha Chermayeff confirmed the tension. “They were spiting each other,” she shared in 2024’s JFK Jr.: An Intimate Oral Biography, co-authored by RoseMarie Terenzio, John’s executive assistant at George. “Maybe Carolyn was trying to make him worry. So then he did it the next night. He was not with her those last two nights.”

Baby Battle

Another point of contention: starting a family. Klein’s book detailed a phone call between John, who the author said dreamed of naming a son Flynn, and an unnamed buddy that took place just two nights before JFK Jr. died. “I want to have kids, but whenever I raise the subject with Carolyn, she turns away and refuses to have sex with me,” John lamented, adding, “It’s impossible to talk to Carolyn about anything. We’ve become like total strangers.”

Carolyn was reluctant to become a mother in the midst of constant scrutiny by the press. “I hate living in a fishbowl,” she told a friend, according to Klein. “John may be comfortable living like this, but I’m not. How could I bring a child into this kind of world?”

Jealousy also plagued their relationship, fueled in part because Carolyn was still secretly seeing Michael Bergin, 56, the Calvin Klein model turned Baywatch actor, even after she moved in with John. “Carolyn was obsessed with Michael,” his former manager Clifford Streit told author Klein. Michael himself admitted to Klein that his connection with Carolyn was strong: “I know deep in my heart that she still loved me even after she married John Kennedy.” At the same time, Carolyn was jealous of her husband’s exes. “When she heard rumors that he was seeing his old flame Daryl Hannah,” Klein wrote, “she flew into a rage.”

Allegations that fights frequently turned violent have also surfaced. In his book, Klein claimed John “told friends that he felt trapped in an abusive relationship.” Indeed, nearly seven months before their 1996 wedding, the couple was photographed screaming at each other in a NYC park. After a tussle over their dog’s leash, photographer Angie Coqueran recounted in a 2024 interview, John “grabbed her hand and pulled off her engagement ring.”

Everything Changed

Yet as bad as things were at the end, there was still hope: Despite the friction of the previous week, in their last hours, after all, Carolyn had agreed to accompany John to his cousin’s wedding. The authors of the oral biography confirmed the pair had been looking at homes outside Manhattan that summer as they contemplated a move and, perhaps, a fresh start. “Everybody always asks me, ‘What do I think would’ve happened?’” their friend Sasha shared with the authors. “Anything was possible.”