NEWSJohn F. Kennedy Jr. Bombshell: Last Person to See Him Alive Had Creepy 'Premonition' Before His Harrowing Death in 1999 Plane Crash
The last person to see John F. Kennedy Jr. alive opened up about having a 'premonition' before his death in a plane crash.
March 14 2026, Updated 4:53 p.m. ET
Aviation analyst Kyle Bailey was one of the last people to see John F. Kennedy Jr., his wife Carolyn Bessette and her sister Lauren Bessette before their tragic and untimely deaths in a plane crash.
On July 16, 1999, the three died after the son of John F. Kennedy flew their plane into the Atlantic Ocean near Martha's Vineyard.
The Night JFK Jr. Died Had 'Iffy' Weather Conditions
JFK Jr. and Carolyn Bessette died on July 16, 1999.
Kyle explained to Fox News how he was "deeply concerned" due to the "iffy" weather that was present during that heated summer night.
"I’ve seen John do that trip many, many times," the pilot, 52, recalled. "It was just a typical Friday night... it was, as we say in aviation, the three H's — hazy, hot and humid. Your typical New York City July day and evening."
The magazine publisher was flying his plane and ran into some bad weather the night he died.
"From my experience, I sensed that, based on those conditions, there probably would be reduced visibility that night up in Martha's Vineyard," he explained. "It didn’t mean I was going to cancel my trip right then, though."
Kyle was just 25 years old at the time of JFK Jr.'s passing and was New Jersey's Essex County Airport when America's Prince arrived in his car and bought a bottle of water and a banana.
He remembered the weather was starting to fog but JFK Jr. didn't seem to be aware of the changing sky conditions. "You really can’t fault him for that, for what he doesn’t know or what he wasn’t told," Kyle said.
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JFK Jr. Took Off in His Plane With Carolyn and Lauren at 8:38 p.m.
Carolyn Bessette's sister Lauren also died with the couple that night.
"I knew from experience on those very hot, hazy, humid summer nights, fog and low visibility could be a problem, especially flying over water," he noted, adding that it would be "challenging" for the George magazine publisher to fly because the weather had "hazy, hot, humid conditions, a partial horizon, and now, on top of that, total darkness."
He then saw JFK Jr. take off in his plane at 8:38 p.m. that ill-fated night. The trio had planned to attend his cousin Rory Kennedy's wedding the following day in Hyannis Port, Mass.
JFK Jr. and Carolyn Bessette married in 1996.
"I went home to my mother that night and said something to the effect of, ‘I just saw JFK Jr. at the airport. I hope he doesn’t kill himself someday in that airplane,’" Kyle sighed.
"I was just concerned for him. Was it a premonition? Possibly. But it was more of a deep concern for John and the two others," he said.
The attorney had been married to Carolyn — who was a former publicist for Calvin Klein — for three years before they died.
