Inside John F. Kennedy Jr. and Carolyn Bessett’s Love Story Before Their Tragic 1999 Deaths

They were the ultimate power-glam couple. John F. Kennedy Jr., the son of the late President John F. Kennedy and Jacqueline Kennedy Onassis — fondly remembered as John-John, the little boy saluting his slain father’s casket — and Carolyn Bessette-Kennedy, a sleek blonde fashionista. Wed in 1996 at the tiny First African Baptist Church on Georgia’s Cumberland Island, the pair seemed destined for happily ever after.

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 to his cousin Rory Kennedy’s wedding plummeted into the Atlantic Ocean off the coast of Massachusetts’ Martha’s Vineyard, instantly killing him, Carolyn, 33, and her sister, Lauren Bessette, 34. Now, as Ryan Murphy’s FX series Love Story features the pair, curiosity about John and Carolyn’s relationship is at an all-time high. The truth is far from a fairy tale. 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, author of 2019’s America’s Reluctant Prince, has said of his friend of 18 years, though he revealed 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.”

Their Last Days

The lawyer and the style icon were struggling before that fateful plane ride. The summer of 1999 marked a stressful time. John’s cousin Anthony Radziwill was in the final weeks of a cancer battle. John was searching for new sources of cash to keep his buzzed-about but financially strapped political magazine, George, afloat. Carolyn was continuing to grapple with life in the spotlight. And they were fighting. In March 1999, they entered marriage counseling, journalist Edward Klein revealed in 2003’s The Kennedy Curse. By July, however, they hit a new low when Carolyn “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, per Klein, “It’s all falling apart.”

Fighting Over Family

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,” he lamented, adding, “It’s impossible to talk to Carolyn about anything. We’ve become total strangers.”

Carolyn was reluctant to become a mother amid 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. Carolyn was still secretly seeing Michael Bergin, 56, the Calvin Klein model turned Baywatch actor. “Carolyn was obsessed with Michael,” his former manager Clifford Streit told Klein. Michael himself admitted to the author 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. Nearly seven months before their 1996 wedding, the couple was photographed screaming at each other in an 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.”

Future Cut Short

As bad as things were at the end, there was still hope, however. Despite the friction of the previous week, in their last hours, after all, Carolyn had agreed to accompany John to his cousin’s wedding. Friend Sasha Chermayeff still wonders what could have been. “Everybody always asks me, ‘What do I think would’ve happened?’” she said in JFK Jr.: An Intimate Oral Biography. “Anything was possible.”