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Live the Gossip > Gossip > Inside JFK Jr. and Carolyn Bessette’s plans to escape NYC before tragic deaths
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Inside JFK Jr. and Carolyn Bessette’s plans to escape NYC before tragic deaths

Written by: News Room Last updated: March 20, 2026
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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.

“[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.”

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.

“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.”

“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.”

Read the full article here

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