John F. Kennedy Jr. and Carolyn Bessette cover PEOPLE magazine for the April 6, 2026, issue.Credit : Getty 

NEED TO KNOW

As Love Story concludes this week, friends of JFK Jr. and Carolyn Bessette recall the relationship struggles of their last summer
After their tragic deaths on July 16, 1999, a friend says of that chapter: “It took on a life of its own because it was the last chapter of their lives”
Still, close friend Sasha Chermayeff tells PEOPLE, “I like to believe they would have survived as a couple, and love would have prevailed”

“His heart was breaking, and I think hers was too.” That’s how Sasha Chermayeff recalls the last summer of her close friends John F. Kennedy Jr. and Carolyn Bessette, whose challenges — the relentless paparazzi, the impending death of John’s cousin Anthony Radziwill from cancer, the fractures in their marriage, the nonstop scrutiny — had only intensified.

By the time John broke his ankle that Memorial Day in a paragliding accident, “they were so disconnected,” says Chermayeff. “That’s what I remember most about that weekend. John was saying, ‘She’s so shut down.’ He meant emotionally. They were shut down from each other. They were at a very important crux.”

John F. Kennedy Jr. and Carolyn Bessette Kennedy arrive at the Kennedy Museum on May 23, 1999.Justine Ellement/The Boston Globe/ Getty 

As the summer continued, so did the heartbreak for the couple, now the subject of the hit FX series Love Story: John F. Kennedy Jr. and Carolyn Bessette, starring Paul Anthony Kelly and Sarah Pidgeon. Nearly 27 years after their deaths on July 16, 1999, the gauzy depiction of their cosmopolitan romance has turned John and Carolyn into a phenomenon anew. It has attracted a legion of Gen Z fans and spawned everything from JFK Jr. look-alike contests (“There’s no such thing as a JFK Jr. look-alike,” says his former executive assistant and close friend RoseMarie Terenzio with a laugh) to a sold-out run of Carolyn’s trademark tortoiseshell headband at C.O. Bigelow, her go-to pharmacy in New York City’s West Village. “It’s surreal after 30 years,” says a close friend, “to see our kids’ generation not only discover them but become so mesmerized by them.”

Along with the buzz has come backlash: John’s nephew Jack Schlossberg, 33, continues to denounce the show’s creator Ryan Murphy, recently telling CBS Sunday Morning, “He’s making a ton of money on a grotesque display of someone else’s life.” And John’s former girlfriend Daryl Hannah, 65, wrote a scathing March 6 New York Times op-ed about the “tragedy-exploiting” series, saying, “Real names are not fictional tools. They belong to real lives.”

Revisiting those lives has also resurrected questions about the state of John and Carolyn’s marriage. “It was just a perfect storm of a young couple trying to figure it out: how they’re going to live, dealing with a struggling business [John’s political magazine George] and just a s—load of pressure during a super hot summer,” says a confidant. “It was a pressure cooker.” Adds another friend: “Had he not crashed the plane, it would have been a meaningless few weeks of tension, but it took on a life of its own because it was the last chapter of their lives.”

Still, there were tender moments, such as the May 1, 1999, White House Correspondents’ Dinner, where John hosted a table for George, accompanied by Carolyn, elegant in her Yohji Yamamoto sheath (black, of course). “John was so proud,” recalls media executive Joe Armstrong, a friend of his mother, Jacqueline Kennedy Onassis. “It was like the peak.” As the dinner ended, John brought over his wife. “He said, ‘Carolyn never knew Mummy. Would you have lunch or dinner with us and just tell her everything about her that was real?’ ” says Armstrong. “We were going to do it later that summer — but there wasn’t enough time.”

John F. Kennedy Jr. helps Anthony Radziwill get ready for his wedding on Aug. 27, 1994.Eric Weiss 

The following weeks were a whirlwind. With Anthony in and out of the hospital, Carolyn often stopped by, bringing him food from his favorite downtown restaurant, Il Cantinori. After John broke his ankle, he told Chermayeff, “Because of this, I’ll just be with Anthony. I won’t be able to get up and bike 20 miles. Anthony won’t be able to go anywhere. I’ll just give him the time he needs before he dies.” Adds Chermayeff: “There were tears in his eyes when he said that.”

Meanwhile, Carolyn was struggling. “She was panic-stricken by the whole thing — all that fame and attention, with all these cameras in her face,” says Chermayeff. “Can you imagine what it was like for her to lose her old life — a life where she was free? And she was such a great girl. She had so much gumption.”

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By then, John had told a few friends, he and Carolyn were no longer intimate. He wanted to have kids. She was fearful of raising a family amid the paparazzi. They began marriage counseling that summer and looked for a second home in Snedens Landing, along the Hudson River, so John could still kayak.

For the first time he sought outside security, a pivotal change for someone who avoided an entourage after losing his Secret Service protection at 16. He contacted Michael Cherkasky, his former boss from the Manhattan D.A.’s office who became the CFO of Kroll security, and told him, “I’m about to start a family with my wife, and I want to think about how I’m going to protect them.” At the same time came the family business: He began contemplating a run for New York governor, telling one of his closest friends, Ed Hill, that May, “Politics is what I know.”

JFK Jr. on crutches in New York on June 10, 1999.Allan Tannenbaum/Getty 

The couple spent their Fourth of July weekend with their close circle: Chermayeff and Brown University pals Robbie Littell and Santina Goodman. “John used to say, ‘I want to be with my family, not my family,’ ” says Chermayeff. “We were his family in a different way, but our being there was also a way to not confront what he and Carolyn needed to confront. They hadn’t figured out how to communicate with each other.”

John planned to fly to the July 17 wedding of his cousin Rory Kennedy in Hyannis Port, Mass., but at first Carolyn said no. According to John’s biographer and friend Steven M. Gillon, author of America’s Reluctant Prince, “He told a friend, ‘If she’s done, I’m done.’ He said they needed to make changes. Otherwise the marriage was going to be over.”

On July 15, after getting his ankle cast removed, John met with the then CEO of Hachette (which owned George), Jack Kliger. The magazine’s funding was no longer guaranteed, and he needed to find investors.

After Carolyn changed her mind about attending the wedding, she and John agreed to drop off her sister Lauren, 34, on Martha’s Vineyard before flying to Hyannis. “He was fighting to turn his life around,” says Gillon. “He was talking to people about ways to turn George into an online magazine. There was hope with his wife. The fact that she went to the wedding was a sign that she was trying. John never gives up.”

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Though accounts vary, he spent at least one night that week, July 15, at the Stanhope Hotel, near his mother’s old apartment on the Upper East Side. He also had lunch with a former girlfriend, Julie Baker, with whom he’d remained friendly. Notes Gillon: “He told her he was afraid of being alone.”

The following day, John told his flight instructor Bob Merena that he didn’t need his help piloting the flight to Cape Cod: “I want to do it alone.” At 6 p.m. he and Lauren drove to Essex County Airport in Fairfield, N.J., where they were met by Carolyn. At 8:39 p.m. the plane took off into the sunset.

Nearly two hours later Terenzio, who was spending the night at John and Carolyn’s apartment because her air conditioner was broken, heard the phone ring. It was Anthony’s wife, Carole Radziwill. Recalls Terenzio: “She said, ‘Thank God, you’re there.’ I said, ‘Carole, it’s Rose.’ She said, ‘Where are they?’ I called the airport. By then it’s 1 in the morning. Bob Merena said the plane took off at 8:39. That’s when I panicked.”

The Kennedy and Bessette families return from a burial at sea for John, Carolyn and Lauren on July 22, 1999.JOHN MOTTERN / AFP/ Getty 

The following afternoon, small fragments of the plane and a few belongings — including Lauren’s garment bag and a bottle of prescription pills labeled with Carolyn’s name — began to wash ashore. On July 21, their bodies were recovered from the bottom of the ocean. The next day, they were returned, in a burial at sea attended by the Bessette and Kennedy families.

Nearly three decades later, friends can’t help but think about what could have been if they hadn’t lost John at 38 and Carolyn at 33. Reflects Chermayeff: “I like to believe they would have survived as a couple, and love would have prevailed. They had it in them to give it another shot.”