Questions swirled around John and Carolyn in the summer of 1999—about their marriage, their careers, their futures, and most of all, what led them to make the tragic choice to board John’s tiny airplane that foggy night in July.
“He was really ahead of his time with that idea, and no one has given him credit for it. The fact that Donald Trump is president proves that what John was saying 20 years ago has come to pass.”
Hanging over John at all times was the question of what, exactly, he would do with his life—and whether he would eventually follow his father and uncles into the family business and seek elected office. After his marriage that potential path became even more fraught, as it would have required the full participation of Carolyn, who guarded her privacy closely. Her distaste for the spotlight that came with being a Kennedy was articulated early on in their relationship.
While John had been born into the public domain and raised to accept with grace the fact that the nation felt an ownership of him, Carolyn went from private citizen to world famous celebrity virtually overnight, a notoriety she did everything she could to play down. She never granted a single interview, and we have almost no examples of her talking on camera.
One source of conflict may have been the question of whether to have children. John was godfather to both of Chermayeff’s children, and she believes that he very much wanted to become a father one day. Carolyn was five years younger than John, and Chermayeff thinks he may have felt ready for parenthood before she did.
In the week leading up to the plane crash there were also questions about whether Carolyn would accompany John to the Hyannis Port wedding of his cousin Rory Kennedy, the youngest of Robert and Ethel Kennedy’s children. It was an event John felt pressure to attend as an ambassador for his branch of the family, since his sister Caroline would not be there. He had his cast removed only the day before the flight. Kliger, Hachette’s CEO, recalls that John was still limping that Friday.
While Carolyn had expressed some hesitation about flying with John, in this instance she agreed to make the trip. Her sister Lauren, who worked for Morgan Stanley and lived near them in Tribeca, chose to travel with the couple. She had weekend plans on Martha’s Vineyard, and John was going to drop her off there before continuing on to Hyannis Port.
The National Transportation Safety Board report on the accident said the probable cause of the crash was “the pilot’s failure to maintain control of the airplane during a descent over water at night, which was the result of spatial disorientation.” It referenced his lack of experience flying without an instructor and the fact that he wasn’t “instrument rated,” which could have helped him navigate the overcast conditions.
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