The last individuals to see John F. Kennedy Jr., along with Carolyn Bessette Kennedy and her sister Lauren, had a sense of “deep concern” as they boarded the ill-fated small plane nearly 30 years ago.
Kyle Bailey, a licensed pilot, was alarmed by the weather that night in 1999 and canceled his own flight from Essex County Airport, where three others were also scheduled to depart.
Though he had a feeling something was off, Bailey didn’t voice his worries to Kennedy, who would later crash into the Atlantic Ocean near Martha’s Vineyard.
“That night, I went home to my mom and mentioned, ‘I just saw JFK Jr. at the airport. I hope he doesn’t end up in a bad spot on that plane one day,'” Bailey recalled in a conversation.
Bailey shared his concerns about the weather that day in a new book, “Witness: JFK Jr.’s Fatal Flight,” which comes as interest in the Kennedy family is rekindled.
On that day, everything seemed usual. The publisher of “George” hurried past Bailey to grab some water and a snack at a convenience store before their flight.
The weather was hot and muggy, typical for a July evening in New York City, but conditions worsened as night fell, leading to poor visibility.
“We noticed that the temperature and the dew point were getting very close together,” he explained. “When that happens, ground fog typically arises. Maybe John didn’t get the right information or was unaware. You can’t really blame him for that.”
Bailey underscored the risks of flying in foggy conditions, especially over water, on those steamy summer nights.
“In John’s situation, taking off later, especially at night, would be more challenging for him,” he noted, referring to Visual Flight Rules. “It felt like you were at the edge of the earth, engulfed in darkness.”
Bailey, despite cancelling his flight, saw Kennedy perform the preflight checks while the Bessette sisters boarded. The plane lifted off at 8:38 p.m.
Bailey wasn’t certain if Kennedy’s instructor was onboard and was unaware of Kennedy’s reported wish to fly solo.
“I noticed three people entering the plane but wasn’t focused on it the entire time, so I didn’t see if the instructor joined. I just assumed he was with them, although conditions felt iffy,” Bailey reflected.
He shared concerns about the new Piper Saratoga, which was more complex than the older plane Kennedy had just sold. “I really wished he had brought an instructor. Was it just a feeling? Maybe. But my worry ran deeper,” he said.
The plan was for Kennedy to transport Lauren Bessette to Martha’s Vineyard before attending a cousin’s wedding in Hyannis Port.
Tragically, the plane crashed shortly after takeoff. Kennedy faced spatial disorientation due to the challenging visual conditions over the water.
The wreckage and the bodies were discovered five days later.
“After such a tragedy, people often ask me, ‘Why didn’t you intervene?'” Bailey said. “But the truth is, we didn’t know who was on that plane with them.”
