John F. Kennedy Jr. developed a passion for flying while trying to “escape” the pressures of his daily life, but his limited pilot skills and recklessness may have caused his untimely death. Episode 9 of the “Fatal Voyage: The Death of JFK Jr.” podcast explores that topic, highlighting the events leading up to the tragic plane crash which killed JFK Jr.; his wife, Carolyn Bessette; and sister-in-law, Lauren Bessette, on July 16, 1999.

The lawyer seemingly had it all in September 1996, as he just exchanged his vows with the stunning Calvin Klein publicist. However, marrying into one of the nation’s most famous families was a shock to the once-private fashion worker, because it meant she would continually be followed around by hordes of paparazzi. Bessette struggled with the constant attention around their relationship and it became a source of tension for them.

On the other hand, JFK Jr. was well-adapted to the limelight. Reporter Andy Tillett says the publisher was so comfortable with it that he made a point of showing how unafraid he was of any potential threats to his life, which made him a target.

John F. Kennedy Jr
Globe Photos/Mediapunch/Shutterstock

As the interest in JFK Jr.’s relationship spiked, he launched George, a magazine and passion project, in 1995. It was a way for him to express himself outside of the political realm — but as his marriage reportedly went through a rough patch in the following years, so did his new venture. At the time, the FBI was also investigating a plan by powerful Colombian cocaine cartels to kidnap him, hold him to ransom and possibly even kill him, simply because of who he was.

It’s no surprise that he needed an escape from the pressures of his daily life. Former National Enquirer editor Barry Levine says JFK Jr. “found it in the skies,” which is why he was determined to get his pilot’s license.

The former president’s son took lessons at the Flight Safety Academy in Vero Beach, Florida, and he later received his private pilot license in April 1998. “He was working on getting his instrument license, and he had passed the written exam and he had passed the performance exam, and all he had to do in order to qualify for his license was to fly, to log hours under the supervision of a flight instructor,” explains historian John Hankey.

By 1999, JFK Jr. had logged about 310 hours of flight time, and was licensed to fly planes with retractable landing gear, a controllable pitch propeller and movable or adjustable flaps. However, that did not deem him as a fully qualified pilot.

Unfortunately, he was still struggling with “remembering what instruments he should have been looking at,” according to air crash investigator Richard Bender. “If you don’t have that scan down when you’re flying on the instruments, you can get in trouble real easy because your body’s telling you, or your brain is telling you’re in one position when in actuality, you’re in some other position. And that’s what they call spatial disorientation.”

John F. Kennedy and Wife

It’s possible this lack of experience resulted in the crash that killed JFK Jr., his wife, and sister-in-law in 1999, though others speculate an ankle injury he previously sustained after crashing his Buckeye Powered Parachute could have contributed to the tragedy.

“He was impaired by a physical injury,” explains Levine. “He had just had a cast [removed] from a paragliding injury that he had, but he needed the cast off his foot so he can operate the plan’s rudder foot pedals. So 24 hours before the flight, John had the cast taken off, and in fact, he was limping.”

However, fellow pilot Kyle Bailey, who was the last man to see JFK Jr. alive, doesn’t believe his limping in the hours before the crash was responsible for the outcome. “There really wasn’t any visible impairment from his ankle injury, other than a slight limp, is what I saw,” says Bailey. “In my mind, that was always secondary, and I kind of viewed that injury … You know, looking back on it … as pretty insignificant, too.”

Looking ahead, the 12-part podcast series will continue to dive deeper into the scandals and coverups leading up to the devastating crash.

New episodes of “Fatal Voyage: The Death of JFK Jr.” are released every Wednesday.

Have a tip? Send it to us! Email In Touch at