More than two decades after the crash that stunned the nation, the last person to see John F. Kennedy Jr. and Carolyn Bessette alive is sharing his account of that fateful night.
Kyle Bailey was 26 years old at the time and worked in aviation. He saw JFK Jr. make the trip from Essex County Airport to Martha’s Vineyard more than a dozen times.
On the night of July 16, 1999, Bailey had also planned to fly to Martha’s Vineyard but canceled his own flight because of the weather.
He described the conditions as the “three H’s” of aviation: hazy, hot, and humid. He feared that John was tempting fate by taking off that evening.
Bailey went home that night and made a grim off-the-cuff comment. “I hope he doesn’t kill himself in that airplane someday,” he recalled saying.
He recounts the tragedy in his book, *Witness: JFK Jr.’s Fatal Flight*.
John and Carolyn were on their way to attend a Kennedy family wedding on Cape Cod, with a planned stopover in Martha’s Vineyard. About an hour after takeoff, the plane crashed into the Atlantic Ocean.
The crash claimed the lives of John, Carolyn, and Carolyn’s older sister, Lauren Bessette, an investment banker at Morgan Stanley. The doomed flight left two families devastated by grief.
The tension between Carolyn’s grieving mother and the Kennedy family was later depicted in the series *Love Story*. In one scene, Ann Freeman pushes back on the focus on Carolyn, reminding those around her that she lost two daughters on that plane.
Ann Freeman eventually settled with the Kennedy family for $15 million. She is reported to have forever regretted allowing Carolyn and Lauren’s remains to be cremated along with John’s and scattered at sea.
The loss of John Kennedy’s plane touched the entire nation in an astonishing way. In the years since, the tragedy has remained a subject of deep public fascination.
Last night on Fox, President Trump also shared his personal memories of Carolyn and John. “I knew them both pretty well,” he said. “They would go down to Mar-a-Lago together and they had a very interesting relationship.”
He described their dynamic as one of bickering and reconciliation. “They would bicker, I don’t want to be nice, they would bicker together and then they’d make up and start kissing wildly,” he recalled.
Bailey’s account adds a new layer to the story of the final hours before the crash, offering a rare glimpse into the moments just before the prince of Camelot and his bride took off for the last time.