Carolyn Bessette-Kennedy’s Mom Warned Her Daughters Not To Board JFK Jr.’s Plane Prior To Crash That Killed Three

In a disturbing recollection, a new book offers a deeper personal look into the tragic events that unfolded 25 years ago on July 16, 1999, when John F. Kennedy Jr.‘s small plane crashed into the waters off Martha’s Vineyard.

The crash claimed the lives of all three aboard – John, 38, his wife Carolyn Bessette-Kennedy, 34, and her sister Lauren Bessette, 33.

The book, JFK Jr.: An Intimate Oral Biography by Liz McNeil and RoseMarie Terenzio, tells how on the evening of the fateful day, Terenzio, Kennedy’s close assistant and friend, had been staying at the Tribeca apartment he shared with Carolyn, as her own air conditioning had broken down. The couple had planned to fly to Martha’s Vineyard that night, drop off Carolyn’s sister Lauren, and then continue on to Hyannis Port, Massachusetts, where they were set to attend a wedding the next day.

However, as the night wore on, Terenzio received a disconcerting call from Carole Radziwill, the wife of John’s cousin Anthony Radziwill. The plane had never arrived at Martha’s Vineyard, and no one could locate its whereabouts.

In a heartbreaking disclosure to Terenzio at the time, Carolyn and Lauren’s mother, Ann Freeman, revealed that she had warned her daughters not to board the small plane. “I told him never to take two of my girls up at the same time,” she said.

“She was angry,” Terenzio shared, “Crying. It was panic, shock. Disbelief.”

Interestingly, Carolyn also had often told her friends and family that she ‘didn’t trust’ her husband’s flying skills as she believed he lacked the patience, diligence and attention span to be a good pilot, according to columnist Maureen Callahan‘s 2024 book Ask Not: The Kennedys and the Women They Destroyed.

The National Transportation Safety Board later determined that the crash was caused by the pilot’s failure to maintain control of the aircraft in a nighttime descent over water, which resulted in spatial disorientation.