In March of 1998, John F. Kennedy Jr. and his wife, Carolyn Bessette, attended the wedding of friends Betsy Reisinger and Kenan Siegel in Miami. Photos from the event show the couple wrapped in a tight embrace, with Bessette’s arms around Kennedy’s neck, her head tilted back as she laughs with abandon.
“Carolyn and John were deeply in love and in love with life,” Betsy recalls in the new book Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy, written by Elizabeth Beller. “That is how I remember them.”
Just sixteen months later, Bessette and Kennedy would tragically die when the single-engine plane Kennedy was piloting crashed into the Atlantic Ocean near Martha’s Vineyard, Mass., on July 16, 1999. (Kennedy, 38, Bessette, 33, and her sister, Lauren, 34, perished instantly.)
Much has been said about the couple; the romance between the charming and handsome son of former President John F. Kennedy and his wife, Jackie, and the stunning and chic Calvin Klein publicist captivated the nation like few others before or since.
Despite reports the pair — who wed in 1996 — were headed for a split prior to their untimely deaths, new revelations tell a different, more nuanced story of their complicated, passionate and enduring relationship. They were in therapy together and were talking about starting a family.
“Toward the end of their lives, they had managed to reach this kind of rapprochement,” The Day John Died author Christopher Andersen shares in the latest issue of Us Weekly. “Whatever friction was there was being dealt with.”
Drawn Together
Kennedy and Bessette met in 1992 when the blond Boston University graduate was working in sales at the Calvin Klein flagship store in Manhattan. Family friend (and The Real Housewives of New York City alum) Carole Radziwill — who was married to Kennedy’s late cousin, Anthony — recalled in a 2016 A&E special that the connection between Kennedy and Bessette was undeniable.
“I met some of John’s previous girlfriends, but I knew the minute he introduced us to Carolyn that she was it,” she said. “He was really besotted with her… There was this instant chemistry.”
According to Beller, the couple spent the early days of their romance going on dinner dates, traveling to Kennedy’s Long Island summer rental and hanging out in Central Park, playing touch football with Kennedy’s pals from Brown.
“[Carolyn] would stay on the sidelines with John’s German shepherd Sam … calling plays, and teasing everyone mercilessly, laughing. John loved it,” Kennedy’s college friend Richard Wiese said in Once Upon a Time.
John-John’s journey! John F. Kennedy Jr. accomplished a great deal before his life was tragically cut short. The son of John F. Kennedy and Jacqueline Kennedy was born in Washington, D.C., on November 25, 1960, two weeks after his father was elected the 35th president of the United States. The Kennedys, who also shared daughter […]
Andersen says Bessette was “very cool, very smart [and] very intoxicating.” Historian Steve Gillon, who wrote America’s Reluctant Prince: The Life of John F. Kennedy Jr. and was a former good friend of Kennedy’s, adds that she “could challenge him intellectually. Carolyn found him, and then she made him work for her. I think that’s one of the reasons he was smitten.”
Kennedy — considered to be one of the world’s most sought-after bachelors — proposed on July 4, 1995; Bessette reportedly made him wait three weeks before she said yes. They tied the knot in an intimate ceremony in front of just 40 guests at a small church on Cumberland Island in Georgia.
Ups and Downs
Their marriage was marked by highs and lows. “There were a lot of issues,” says Gillon. Bessette hated being thrust into the spotlight and hounded by the paparazzi, and she resented Kennedy for it.
“John had grown up with this media presence his whole life; it didn’t bother him,” explains Gillon. “But Carolyn was terrified. She became more reclusive.”
They fought, sometimes publicly. (Photos of them arguing at NYC’s Washington Square Park made front-page news in 1996.)
As America’s unofficial royal family, the Kennedys have been rubbing elbows with some of the biggest names in Hollywood for decades. In the 1960s, John F. Kennedy forged friendships with the likes of Judy Garland and Frank Sinatra, the latter of whom actively campaigned for JFK to be elected to the White House. The 35th […]
“They were both very high-strung, and I think they had tempers,” says Andersen. (Gillon recalls a fight the pair had in the kitchen of their Tribeca loft over a letter Kennedy received from his boss at his political magazine, George, during which Bessette “lit into” Kennedy for not sticking up for himself more.)
“We saw several arguments they had in public,” adds Andersen, “but by and large, people thought Carolyn was worth it.”
JFK Jr and Carolyn Bessett. Arnaldo Magnani/Getty Images
Working It Out
There was a turning point towards the end. Beller revealed Kennedy and Bessette had started couples counseling a few months before their deaths. The author also dispels reports that the pair had fought in the hours leading up to the flight to his cousin Rory’s wedding over Bessette delaying the trip to get a pedicure.
“An eyewitness report has her leaving there by 5 p.m.,” Beller writes. In J. Randy Taraborrelli’s book The Kennedy Heirs, the author writes that Bessette had initially declined to attend the wedding but changed her mind several days later because she knew how important it was to her husband.
They were discussing having kids as well. “[John] even had a name picked out,” says Andersen. “[Whether] it was a boy or a girl, they were going to call the child Flynn.” Bessette was coming around after having reservations about bringing a baby into the mix with all of the media attention they garnered.
“She was doing much better in the closing weeks of their marriage,” Andersen says. “John was making accommodations for Carolyn and she was finally making them for him.”
Gillon says he believes Kennedy and Bessette were in love and would’ve made it in the long run if given the chance. He tells Us a former doctor of Kennedy’s recently told him he caught Kennedy and Bessette making out in his office a few weeks before the crash.
“He said, ‘John, get a room!’” Gillon recalls with a laugh. “I think that’s a pretty good indication that they were still really attracted to each other.”
Things were looking up. “Carolyn had found a way to cope with all of the attention,” says Andersen. “They had found a way.” Kennedy (who’d finally decided to follow his father’s footsteps into politics — “that was his calling,” says Gillon) was feeling hopeful, Andersen adds. “Days before he died, John said, ‘I’m happy with where my life is now.’”
For more on Kennedy and Bessette, watch the video above — and pick up the latest issue of Us Weekly, on newsstands now.
With reporting by Christina Garibaldi & Andrea Simpson