JFK Jr.’s Career and Marriage Were ‘Weighing’ On Him Before Fatal Plane Crash

“Make no mistake, in the ’80s and ’90s, JFK Jr. was a huge celebrity,” reporter Andy Tillett notes. “He’d not only inherited his father’s name, but he had all his good looks, charm and big personality too. The only question was — what was he going to do with himself?”

In fact, JFK Jr. seemed much less interested in following in the footsteps of his father, John F. Kennedy, and countless other family members by becoming a politician than pursuing the life of a thespian.

“He wanted to be an actor and he could have been a great actor,” author Doug Wead says. “All through history, the children of presidents have been on the stage … he probably would have been great at it, but his mother Jackie Kennedy put her foot down, absolutely not. It was kind of like, ‘I’m not saying you have to be president, but you can’t be this, you can’t be that, you can’t be this … ”

“Before her death, she sent him a note that said, ‘You especially have a place in history,'” Wead adds. “He had to have felt that all his life, even though she never said it.”

As much as JFK Jr. clearly cared for his mother, reporter Leon Wagner notes on the podcast that he may have had mixed feelings upon her passing in 1994.

“Obviously it was a blow. He loved his mother,” Wagner says. However, he also seemed to see her death as an opportunity to follow his own dreams. “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.”

As far as choices go, one of the most important ones JFK Jr. could have made was his decision to marry Carolyn Bessette. They started dating in 1994 and the next year, she moved into his Tribeca apartment and they became engaged. They were married in September 1996 in a private ceremony — quite the challenge, considering the media attention JFK Jr. was constantly plagued by.

But their relationship soon turned sour. “His wife … constantly had drugs all over their apartment and used when they traveled and what have you,” Wagner claims. “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 Bessette had an affair with a model during their marriage. “By summer 1999 they were pretty much separated,” Tillett says. At the same time, JFK Jr.’s professional life was also falling apart.

In 1995, JFK Jr. and his friend Michael Berman founded George, a monthly lifestyle magazine. “The tagline was ‘Not just politics as usual,'” narrator and ex-homicide detective Colin McLaren explains. For all intents and purposes, it did very well — at first.

“His old friends, the president’s old friends, told John F. Kennedy Jr. that his ‘dad always wanted to be a publisher. His dream was to be a publisher, he never wanted to go into politics,'” Wead says. “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.”

“That was part of his creating something completely on his own and taking charge of his life,” Wanger adds. “Which he had never been allowed to do as long as Jackie was alive because she would always interfere and she would criticize him.”

Unfortunately, the success was short-lived. While George once held the largest circulation of any political magazine in America, readers quickly left — and so did advertisers. Within just a few years, JFK Jr. was scrambling to keep George magazine alive.

“It was just the exact wrong time to start a big flashy magazine,” Wagner says. “It was the dawn of the internet. It was just a different thing. And magazines like that just weren’t going to work no matter how good they were. And George started to flounder.”

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

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

When JFK Jr., Carolyn and her sister, Lauren Bessette, arrived, Bailey claims that the couple stood away from Lauren and appeared to be engaging in a “serious discussion.” The podcast notes 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., and the discussion could have been about them being late.

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 reveals. Sadly, JFK Jr., his wife and his sister-in-law never made it to the wedding.

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

The death of JFK Jr. shocked the world, and “Fatal Voyage: John F. Kennedy Jr. Case Solved” promises to go into further detail about his death and the strangeness of the autopsies on the bodies after in future episodes. To learn more, listeners can tune into the series every Wednesday.