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Inside JFK Jr. and Carolyn Bessette’s plans to escape NYC before tragic deaths: ‘She wanted freedom’

March 20, 2026
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Inside JFK Jr. and Carolyn Bessette’s plans to escape NYC before tragic deaths: ‘She wanted freedom’

John F. Kennedy Jr. and Carolyn Bessette were looking to leave New York City before their tragic deaths after the relentless paparazzi attention became increasingly difficult for her to endure.

JFK Jr.’s close friend, Sasha Chermayeff, exclusively told Page Six that Bessette went house-hunting in the suburbs shortly before the couple died in a 1999 plane crash.

“They were looking to buy a place outside of the city, and she came up and stayed with me here,” Chermayeff, who lives in Upstate New York, shared.

John F. Kennedy Jr. in a tuxedo and Carolyn Bessette Kennedy in a black dress attending the John F. Kennedy Library Foundation dinner.
Carolyn Bessette and John F. Kennedy Jr. (seen here in 1999) wanted to move out of New York City before their tragic deaths. Getty Images
John F. Kennedy Jr. in a flat cap and Carolyn Bessette-Kennedy in sunglasses walking on a city street.
Sasha Chermayeff, JFK Jr.’s high school friend, exclusively told Page Six that Bessette (seen here with Kennedy Jr. in 1999) went house-hunting in the suburbs. William Regan/Globe Photos via ZUMA Wire / Shutterstock

“[Bessette] was looking at like, maybe we can’t live in New York City. Maybe we have to, you know, figure out a different life so that she wasn’t going to be followed,” she said.

Kennedy Jr. and Bessette were also looking at other locations outside of the Empire State.

“They were looking in other places [too]. They were looking all around,” Chermayeff said.

Bessette and Kennedy Jr. were considering properties with long driveways that would keep them far from photographers, the late couple’s friend explained

“She wanted freedom,” Chermayeff said. “She wanted some kind of way to get past this, and she hadn’t figured it out yet.”

John F. Kennedy Jr. and Carolyn Bessette Kennedy departing the Washington Hilton after the White House Correspondents Dinner.
“They were looking to buy a place outside of the city, and she came up and stayed with me here,” Chermayeff, who lives in Upstate New York, said of JFK Jr. and Bessette (seen here in 1999). Getty Images
John F. Kennedy Jr. and Carolyn Bessette Kennedy walk their dog on a city street.
The couple (seen here in 1997) lived in a Tribeca apartment after tying the knot. Getty Images
Publicist Carolyn Bessette-Kennedy and publisher John F Kennedy Jr. at an awards event.
Bessette (seen here with her husband in 1999) wanted to escape the relentless paparazzi, we’re told. Ron Galella Collection via Getty Images

After Bessette and Kennedy Jr. tied the knot in 1996, the Calvin Klein publicist was so “scared” of the hungry tabloids following her every move that she would rarely leave their Tribeca apartment.

“She started to get a little agoraphobic,” Chermayeff said. “So many photographers just harassed [her].”

Bessette went from having this fun, full social life in downtown Manhattan to staying indoors and away from it all.

“The next thing you know, you can’t go anywhere and you are being followed,” she said. “It was hard. Really, really hard.”

While Kennedy Jr. was used to living in the spotlight, Bessette really didn’t know what she was getting into when she married the son of President John F. Kennedy and Jacqueline Kennedy Onassis.

“I mean, John wasn’t struggling with [the media attention]. John was struggling with the fact that it was really hard for [Carolyn],” Chermayeff shared. “He had no problem with it. He didn’t know anything other than that.

John Kennedy Jr. in a tuxedo and Carolyn Besset in a white shirt and black skirt.
“She wanted freedom. She wanted some kind of way to get past this, and she hadn’t figured it out yet,” Chermayeff said of Bessette (seen here with Kennedy Jr. in 1999). Getty Images
John Kennedy Jr. and his wife Carolyn Bessett under an umbrella at the Newman's Own/George Awards.
Kennedy Jr. (seen here with his wife in 1999) was used to the media attention, but Bessette struggled. Getty Images

“His whole life was being this little center of attention in the world, and he had fully reconciled [with] it and was completely at home with it.”

Their honeymoon in Istanbul was a “harsh wake-up call” for Bessette, Chermayeff said.

“Istanbul was very special, but I also think that was the beginning of them realizing that they were going to be followed everywhere,” Chermayeff recalled. “Carolyn was coming to this sort of realization that… getting off a plane in a faraway place wasn’t going to mean that you were going to have privacy.”

Bessette and Kennedy Jr. miraculously had a moment of total privacy for their secret wedding on Cumberland Island, a secluded isle off the coast of Georgia.

Helicopters had circled the Greyfield Inn where guests were getting ready before the wedding, Chermayeff recalled. But all 40 attendees were able to sneak off the property in jeeps and get to the ceremony location without being detected.

“We had lost the helicopters and they weren’t able to find the cars,” she said. “The beautiful ceremony was able to happen in silence with the water and not with the press, so it was a super lucky thing.”

John F. Kennedy Jr. in a tuxedo, holding hands with Carolyn Bessette in a strapless black dress.
“John was struggling with the fact that it was really hard for [Carolyn],” Chermayeff shared of the duo (seen here in 1998). Getty Images
John F. Kennedy Jr. kissing Carolyn Bessette on the cheek.
The pair (seen here in the year of their deaths) died in a 1999 plane crash — three years after they secretly wed. Getty Images

“We were all happy about that. They just didn’t find us. So it’s like a miracle,” she said.

Despite mounting tensions due to the media circus surrounding their marriage, Bessette’s love for Kennedy Jr. never wavered.

“I mean, what can I say? It was like electricity — it wasn’t for show,” Chermayeff said. “There was so much energy between them. You could see it and feel it all the time.”

The post Inside JFK Jr. and Carolyn Bessette’s plans to escape NYC before tragic deaths: ‘She wanted freedom’ appeared first on Page Six.

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