John F. Kennedy Jr. Was Under ‘Pressure’ in His Personal Life Prior to Fatal Plane Crash

John F. Kennedy Jr. ‘May Have Had a Death Wish
John F. Kennedy Jr. Shutterstock

The great unknown. A new episode of the “Fatal Voyage: John F. Kennedy Jr. Case Solved” podcast dives deeper into who John F. Kennedy Jr. was becoming before he suddenly died in a 1999 plane crash. Episode 3 of the podcast, “John Boy’s Path (The Good Years),” explores how much turmoil was in his personal life and how it may have impacted the decisions he made that fateful night.

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“He always lived his life with grace and style,” John Koerner, author of Exploding the Truth: JFK Assassination revealed on the podcast. “He was the type of person I think we, even now, could remember because he lived above politics, [and was] loved by all people, and there are so few like that anymore.”

JFK Jr.’s mother, Jackie Kennedy, put a tremendous amount of pressure on him from a young age. “Before her death, she sent him a note that said, ‘You especially have a place in history,’” author Doug Wead said. “He had to have felt that all his life, even though she never said it.”

When Jackie died in 1994, JFK Jr. told friends he had been reborn, reporter Leon Wagner revealed on the podcast. “He told the friends that he had been born again when she died, that he was free, and he would make his own decisions, make his own mistakes, what have you,” Wagner said.

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As far as choices go, one of the most important ones that JFK Jr. could have made was his decision to marry Carolyn Bessette, who also died in the plane crash, along with JFK Jr.’s sister-in-law Lauren Bessette.

John F. Kennedy Jr. ‘May Have Had a Death Wish
John F. Kennedy Jr. and Carolyn Bessette. Shutterstock

JFK Jr. and Carolyn began dating in 1994 and the next year, she moved into his Tribeca apartment and they got engaged. They were married in September 1996 in a private ceremony, but their relationship soon turned sour.

“His wife constantly had drugs all over their apartment and used [drugs] when they traveled and what have you,” Wagner claimed. “And he certainly didn’t want to get arrested, given who he was and all that … She used cocaine regularly, and he had several screaming fights with her.”

The duo continued to fight, and Carolyn eventually had an affair with a model during their marriage. “By summer 1999 they were pretty much separated,” Tillett said. At the same time, JFK Jr.’s professional life started to fall apart.

The duo continued to fight, and Carolyn eventually had an affair with a model during their marriage. “By summer 1999 they were pretty much separated,” Tillett said. At the same time, JFK Jr.’s professional life started to fall apart after the magazine he founded with friend Michael Berman in 1995, George, was no longer profitable.

“His old friends, the president’s old friends, told John F. Kennedy Jr. that his ‘dad always wanted to be a publisher.’ That was a great moment in his life when he published George, and it was a great magazine, and it was a wonderful reflection of him,” Wead said. “That was part of his creating something completely on his own and taking charge of his life, which he had never been allowed to do as long as Jackie was alive because she would always interfere and she would criticize him.”

John F. Kennedy Jr. ‘May Have Had a Death Wish
John F. Kennedy Jr. Shutterstock

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Just as his marriage was failing and his pet project was unraveling, JFK Jr. decided to attend his cousin Rory Kennedy‘s wedding in Martha’s Vineyard. “It was against this turbulent professional and personal backdrop that John prepared to fly,” McLaren said.

Wead speculated that “John F. Kennedy Jr. may have had a death wish when he took that plane up.”

Fellow pilot Kyle Bailey was one of the last people to ever see the son of JFK alive, and he revealed on the podcast that he was going to fly the same day that JFK Jr. did, but decided not to when he became “very concerned with the deteriorating weather conditions.”

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When JFK Jr., Carolyn and Lauren arrived at the plane, Bailey claimed that the couple stood away from Lauren and appeared to be engaging in a “serious discussion.” The podcast noted that the publisher planned to leave no later than 6 p.m. that evening — but didn’t even arrive at the airport until around 8 p.m.

When the plane finally took off, Bailey watched it go. “You know, I kind of thought to myself then, and I said to my family later, ‘You know, I hope he had an instructor on the airplane with him, because of the conditions,’” Bailey recalled. Sadly, JFK Jr., his wife and his sister-in-law never made it to the wedding.

“The things that were on his mind [at the time were], the end of the magazine [and] the end of his marriage. All of this was weighing on him,” Wagner mused on the podcast. “So, with all this pressure, he’s trying to fly this plane and he just got lost in the fog.”

To learn more, tune into “Fatal Voyage: The Death of JFK Jr.” every Wednesday.

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