“They were at a very important crux” in July 1999 according to friend Sasha Chermayeff.

JFK Jr. and Carolyn Bessette were ‘disconnected’ before fatal plane crash: ‘His heart was breaking’

"They were at a very important crux" in July 1999 according to friend Sasha Chermayeff.

By Marina Watts

Marina Watts

Marina Watts is a news writer for with seven years experience covering entertainment, pop culture and celebrity news. Her previous work appears in PEOPLE, Bustle and Newsweek.

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March 25, 2026 12:00 p.m. ET

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John F. Kennedy Jr. and Carolyn Bessette Kennedy in Boston in May 1999. Credit:

Justin Ide/Newsmakers via Getty

- John F. Kennedy Jr. and Carolyn Bessette's close friend Sasha Chermayeff told PEOPLE magazine that the couple was "disconnected" in the weeks before the fatal plane crash.

- "His heart was breaking, and I think hers was too," she said of the *Love Story *couple's final days.

- Chermayeff said she believed the couple would've eventually patched things up had their plane not crashed off Martha's Vineyard on July 16, 1999.

With the finale of *Love Story: John F. Kennedy Jr. & Carolyn Bessette** *on the horizon, one of the couple's real-life friends has come forward to say tensions were rising in the final weeks of the couple's lives.

Speaking with PEOPLE in an article published on March 25, Sasha Chermayeff reflected on Kennedy and Bessette's marriage leading up to their fatal plane crash in July 1999. "His heart was breaking, and I think hers was too," she told the publication.

"They were so disconnected," Chermayeff added of the political scion and former fashion publicist. "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."

As tabloid scrutiny of the couple became increasingly relentless, *George *magazine struggled, and their marriage suffered, JFK Jr.'s cousin Anthony Radziwill was dying after being diagnosed with sarcoma in 1994. And then Kennedy broke his ankle.

"'Because of this, I’ll just be with Anthony,'" Chermayeff remembered him saying. "'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.' There were tears in his eyes when he said that."

Radziwill died less than a month after his cousin, in August 1999.

John F Kennedy Jr. and Carolyn Bessette in New York in November 1997.

Ron Galella Collection via Getty

Meanwhile, per Chermayeff, Bessette was "panic-stricken." "All that fame and attention, with all these cameras in her face. 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."

Chermayeff added that the couple spent July 4 weekend with a group of friends. "John used to say, 'I want to be with my family, not *my family*,'" she said. "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."

Ultimately, Chermayeff would "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."

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JFK Jr. and Bessette's relationship has been dramatized by the FX series *Love Story: John F. Kennedy Jr. and Carolyn Bessette*, starring Paul Anthony Kelly and Sarah Pidgeon.**

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Kennedy, Bessette, and Carolyn's sister Lauren Bessette died in a plane crash off the coast of Martha's Vineyard on July 16, 1999. They were dropping off Lauren on their way to Cape Cod for Kenney's cousin Rory's wedding when the plane Kennedy was piloting plummeted into the ocean.

After days of searching, their bodies were recovered from the ocean on July 21. It was determined all three died on impact.

The *Love Story *finale airs on Thursday, and will be available to stream on Hulu the next day. According to *Love Story *star Constance Zimmer, it will "be very, very difficult for everybody to watch." "I think we all know what's coming," Zimmer told Decider. "It's just how we're telling it."**

John F. Kennedy Jr. and Carolyn Bessette. Rose Hartman/Getty Images

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