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Carolyn Bessette-Kennedy didn't think JFK Jr. should fly planes

Martha Ross, The Mercury News on

Published in News & Features

Carolyn Bessette-Kennedy is the subject of two new books, which in various ways seek to counter the image of her as the superficial, vain, cocaine-addled “harridan” who made the last months of John F. Kennedy Jr.’s life miserable.

In fact, it may have been the other way around when it came to being self-centered, with the only son of John F. Kennedy and Jacqueline Kennedy Onassis coming off as entitled, reckless, narcissistic and not all that bright in at least one of the books.

What’s not disputed is that “America’s prince” should not have been flying on his own the night of July 1999, when his small Piper-Saratoga plane crashed into the Atlantic Ocean, killing him, Bessette-Kennedy and her sister Lauren Bessette.

The National Transportation Safety Board blamed the crash off Martha’s Vineyard on pilot error and said that Kennedy Jr., 38, lacked experience in flying at night without an instructor and had not yet qualified for flying with instruments alone, as opposed to seeing visual clues out the window, The New York Times reported in 2000.

One long-held belief about the night of the crash, which both books dispel, is that Bessette-Kennedy, 33, somehow caused it because she kept her husband and sister waiting at the airport while she made a pedicurist redo her toe-nails three times.

All three were late arriving to the airport in New Jersey because they were stuck in traffic, Elizabeth Beller writes in “Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy,” according to People. The plan was for Kennedy to drop Lauren Bessette off in Martha’s Vineyard before flying with his wife to a Kennedy family wedding in Hyannis Port.

Leading up to the night of the crash, Bessette-Kennedy regretted the trip and letting her husband fly them to the wedding, according to the book, “Ask Not: The Kennedys and the Women They Destroyed,” by Maureen Callahan, a columnist for the Daily Mail.

“I don’t trust him,” she had said to family and friends, according to an excerpt of Callahan’s book in the Daily Mail.

Bessette-Kennedy didn’t think her husband of three years “had the patience, diligence or attention span to be a good pilot,” Callahan wrote. He wasn’t taking his training seriously, and he had not banked nearly enough hours in the air to fly alone, “yet he regularly broke the rules, sneaking in solo flights when he was supposed to have an instructor with him.”

Not one person admonished him or threatened to take away his training certificate, Callahan also wrote. “No, it was just John being a Kennedy, a rogue like his much-adored father,” Callahan said.

Moreover, Kennedy was recovering from a broken ankle and faced months of physical therapy, Callahan wrote. His cast had come off the day before the flight.

But Kennedy swore that his doctor had cleared him to fly that night, according to Callahan. An instructor also had offered to fly with him that night, but Kennedy said ”he wanted to do it alone,” the NTSB said in its report on the crash.

Callahan’s book suggests that Kennedy may have had “a death wish” at the time of the crash. He had always been “reckless.”

Back in 1986, he nearly killed his first serious girlfriend, a woman named Christina, by taking her kayaking in the open sea off Jamaica, without life jackets, and with no experience in navigating the open sea, Callahan wrote. During the ordeal, Kennedy and Christina were nearly pushed by strong currents into a boulder, crash-landed on a beach and at several points were plunged underwater.

“We could have died,” Christina told Kennedy when they finally reached land, according to Callahan.


“Yeah,” he said. “But what a way to go.”

Before their fatal flight, Kennedy and his wife were experiencing trouble in their marriage, according to Beller’s book. They had begun dating in 1994, before the death of his mother, and married in a small private ceremony in 1996.

Kennedy and Bessette-Kennedy, a former publicist for Calvin Klein, had begun marriage counseling, as he was dealing with the impending death of his beloved cousin, Anthony Radziwell, and the pressures at his political magazine, George, Beller wrote, according to People. Meanwhile, Besette-Kennedy was having trouble being in the spotlight, with photographers constantly camped outside the door of their Tribeca condominium building.

“They were both very sympathetic to what the other one was going through, but also getting a little impatient,” Beller told People. She said it was, “When will things be OK at George? When will we stop having to have every night be about going out to promote the magazine or look for advertisers?’ And (John) felt like, ‘When are you going to be able to handle the press, because it’s not going to go away?’”

But there also were reports that Bessette-Kennedy was having an affair with Calvin Klein model Michael Bergin, which Bergin himself admitted in his 2005 book, “The Other Man,” according to People. Vanity Fair also reported in 2014 that Bessette-Kennedy’s “insecurity fueled a need to control and manipulate; her frequent use of cocaine made her paranoid.” She also was jealous of his older sister, Caroline, and his George business partner, Michael Berman.

Callahan wrote that Kennedy had actually moved out of their Tribeca loft and might have taken up again with ex-girlfriend Daryl Hannah. He also was telling friends that his wife was “crazy,” that she had five times-a-week therapy sessions and a nasty drug habit and that refused to have sex with him.

Beller believes that Kennedy and Besette-Kennedy were still trying to make their marriage work, and that’s why she agreed to accompany him to the family wedding.

“I know (Carolyn) didn’t want to go to the wedding,” Baller told People.

But Bessette-Kennedy also may have felt pressure to go, because Kennedy told her that the press “would be all over them” if he went to the wedding alone, according to Beller.

According to Callahan, Kennedy needed his wife to go with him. He also was under pressure because his magazine, which tried to combine pop culture and politics, was “collapsing.” George had gone from being one of the most successful launches in magazine history to a spectacular failure, Callahan wrote.

The last thing Kennedy wanted was the press speculating about his marriage. Kennedy’s assistant strongly advised Bessette-Kennedy to join him on the flight because, “otherwise the media would report they were getting divorced.”

Bessette-Kennedy knew that if their marriage failed, she’d be blamed, Callahan wrote. She wanted out of the marriage, but felt trapped. “I can’t get a divorce,” she would say, according to Callahan. “I’ll wind up living in a trailer park, out of my mind, going: ‘I used to be married to JFK Jr.'”


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