Last person to see JFK Jr. alive had premonition and ‘deep concern’ ahead of his doomed flight
Nearly 30 years after the fatal plane crash that claimed the lives of John F. Kennedy Jr., his wife Carolyn Bessette Kennedy, and her sister Lauren Bessette, the last person known to have seen them before takeoff says he felt uneasy about the conditions that night.
Kyle Bailey, a licensed pilot, had been at Essex County Airport the evening of the 1999 flight. Because of concerns about the weather, he decided not to fly his own plane that night. Kennedy and the Bessette sisters were preparing to depart from the same airport.
Looking back, Bailey says the conditions gave him a troubling feeling, though he never voiced those concerns to Kennedy. Speaking to Fox News, he recalled telling his mother later that evening, “I just saw JFK Jr. at the airport. I hope he doesn’t kill himself someday in that airplane.”
Bailey describes what he saw that day in his book “Witness: JFK Jr.’s Fatal Flight,” written during a time when public interest in the young Kennedy couple has grown again.
Earlier in the day, nothing seemed unusual. Kennedy, publisher of George magazine, walked quickly past Bailey at the airport convenience store to grab a bottle of water and a banana before his flight. The weather felt typical for a summer day in New York City—hot and humid—but as the evening progressed, visibility started to decline.
Bailey noticed the temperature and dew point were moving closer together, something pilots recognize as a warning sign for potential fog. When that gap shrinks, ground fog can develop quickly, reducing visibility.
He explained that Kennedy might not have been aware of how much the conditions could change, noting that pilots can only act on the information they have at the time. From Bailey’s experience, hot and hazy summer nights—especially flights over water—can make visibility much worse after dark.
Kennedy was scheduled to leave later than Bailey had originally planned, which meant he would be flying in full darkness. For a pilot operating under visual flight rules, losing the horizon at night can be extremely disorienting, particularly over open water where there are few visual references.
Bailey ultimately canceled his own flight but remained at the airport long enough to see Kennedy prepare for departure. He watched as Kennedy completed his preflight checks and as Carolyn and Lauren Bessette boarded the aircraft. The Piper Saratoga lifted off at 8:38 p.m.
Bailey said he did not see whether an instructor joined the group before takeoff. He later learned Kennedy had reportedly told his instructor he wanted to fly the trip alone.
“I saw the three of them board the plane,” Bailey said. “But I wasn’t watching the aircraft the entire time, so I couldn’t tell if an instructor walked over there. I hoped he had one with him because the conditions weren’t ideal.”
He also noted that the Piper Saratoga was relatively new to Kennedy. The aircraft was more complex and higher performance than the older plane Kennedy had recently sold, which added to Bailey’s concerns.
Kennedy’s plan that evening was to fly to Martha’s Vineyard, where he would drop off Lauren Bessette, before continuing with his wife to Hyannis Port for his cousin’s wedding.
According to investigators, the aircraft went down in the Atlantic Ocean off Martha’s Vineyard a little more than an hour after takeoff. Officials concluded Kennedy experienced spatial disorientation while flying over the water in limited visibility. The wreckage and the bodies of the three victims were located five days later.
After the crash, Bailey said some people questioned why he didn’t try to stop Kennedy from leaving.
Bailey says he had no way of knowing whether an experienced instructor was already on board. Because of that uncertainty, he chose not to intervene and instead hoped Kennedy had someone more experienced flying with him that night.
About Post Author
