John F. Kennedy Jr. Looked For An ‘Escape’ In Weeks Before Untimely Death Says New Book

John Kennedy Jr. with wife Carolyn Besset arrive at "Bright Night Whitney", a retrospective celebration of a century of American art at the Whitney Museum in New York City March 9, 1999.
Diane Freed / Getty Images

John F. Kennedy Jr. was reportedly troubled in the weeks before his untimely death in a plane crash alongside wife Carolyn Bessette and her sister Lauren Bessette, looking for an “escape” from the difficulties he faced in his life. A story recently published by Vanity Fair cited a new book titled Four Friends: Promising Lives Cut Short by William D. Cohan, which speaks of Kennedy’s unhappiness and troubled times in the weeks leading up to his death.

Kennedy was reportedly having issues with wife, Carolyn, who was unhappy living in the glare of the media spotlight since their 1996 wedding. The couple had drifted further and further apart, according to the book, and by the time of their ill-fated flight to attend the wedding of John’s cousin Rory Kennedy at Martha’s Vineyard, John had reportedly moved out of the Tribeca home the two had shared since their marriage.

The Vanity Fair story quoted John’s good friend Sasha Chermayeff, who stated that after the couple’s secret wedding on Cumberland Island, Georgia “everything changed” between John and Carolyn. “She got nervous as hell,” Chermayeff said. “It sort of went down and down, and by the last year, they were not able to communicate, like not at all.”

John was also reportedly dismayed at his relationship with his only sister, Caroline. The two were barely on speaking terms for almost an entire year prior to John’s death, the book claims. Apparently, there was a dispute between the siblings as to what should be done with the family memorabilia at the Kennedy compound in Hyannis Port.

The Vanity Fair story also cited the issues with John’s first solo public venture as an adult, George Magazine, which was floundering in the months leading up to the crash. The Cohan book claims that John met with Jack Kliger, his boss at Hachette Publishing, on the day of his death to discuss how they could better formulate the magazine for success.

John was also nursing a broken ankle, an injury he picked up in a paragliding accident over Memorial Day weekend just six weeks before the fatal plane crash occurred. He was upset over the injury because it might physically slow him down for the summer — a time of year when he enjoyed outdoor activities such as swimming, running, biking, kayaking and rowing.

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Kennedy, Carolyn and Lauren Bessette were killed after John, a pilot that was still in training to use instruments, flew on sight only that evening. He had reportedly been working on getting an instrument rating. The flight took off after 8:30 p.m. and the weather was apparently overcast and hazy, making it difficult to see — two factors that led to the crash. The New York Times called Kennedy a “cautious” flyer who often took a flight instructor with him on his flights to Martha’s Vineyard. On the night of Kennedy’s crash, there was no instructor aboard.

John F. Kennedy Jr, Carolyn and Lauren Bessette died on July 16, 1999.