20 Years After JFK Jr.’s Untimely Death, A Close Friend Has Come Clean About His Darkest Secrets

The plane crash which killed Kennedy Jr. is still a matter of some controversy today. The term “the Kennedy curse” still hangs over the family. President Kennedy was famously assassinated, of course. One of his other sons, Patrick, was born prematurely and died while still an infant. And a third child of the president and his wife Jackie was stillborn.

That isn’t all, however. President Kennedy’s brother Robert was assassinated in 1968 – an incident which is still the basis for many conspiracy theories. Robert’s fourth child, David Anthony Kennedy, died of a drug overdose. And his sixth, Michael LeMoyne Kennedy, was killed in a skiing accident in 1997.

But was the death of Kennedy Jr. and two other people the fault of the family curse? Despite his friendship with the man, Gillon places the blame for the plane crash firmly on Kennedy Jr. himself. After all, he hadn’t even completed his flying lessons when he decided to pilot himself, his wife Carolyn and his sister-in-law Lauren to a wedding.

At the time when Kennedy was flying the plane, weather conditions were poor enough to obscure landmarks which could be used for piloting. It was still legal for Kennedy to be flying, but it was certainly problematic. After the crash, the National Transportation Safety Board would declare “spatial disorientation” to have been a contributing factor to the accident.

The plane went down on July 16, 1999, and the bodies were recovered on July 21. All of the victims had been killed on impact, the county medical examiner asserted. Kennedy Jr.’s body was cremated, and his ashes scattered into the Atlantic Ocean. Flags at the White House flew at half-mast in his honor.

Gillon believes that Kennedy Jr. is solely responsible for the accident. While promoting his book, he told People, “He should not have gone up that night. At the first sign of danger, he should have done what a lot of pilots did that night and flew inland, away from the ocean, spend the night somewhere and then pick up the next morning.”

Gillon went on, “It was [Kennedy’s] poor judgment that led to his death and the death of his wife and his sister-in-law, and there’s no way around that. John bears the responsibility of his recklessness that night and John alone. That is not easy for me to say, but when I wrote this book I decided my responsibilities as a historian superseded my responsibilities as a friend.”

The same thing could be said for every aspect of Kennedy Jr.’s life which Gillon’s book delves into. It begins by detailing his childhood. According to Gillon, Jackie Kennedy was not a very hands-on mother to her children. Apparently, she usually left John and his sister Caroline in the care of nannies while she travelled.

Gillon claimed in his book that Jackie Kennedy could often be away from her children for “weeks at a time.” And before she would go out traveling, he wrote, “Mrs. Kennedy would fill out postcards to be given to Caroline and John every day that she was away.” Yet she did supposedly ensure that they were taught to be mannerly and considerate.

Of course, the family’s lives changed the day President Kennedy was assassinated. In order to spare them, news of their father’s death was initially kept from John and Caroline. Ben Bradlee – then the editor of The Washington Post – watched over the children with his wife as helicopters circulated the White House.

Gillon paints a picture of the tragic scenario in his book. “Every time John and Caroline heard the whir of a helicopter rotor approaching, they raced to the windows, shouting, ‘That’s Mummy and Daddy! Mummy and Daddy are coming home!’” he wrote. “Unsure what to say, Bradlee simply responded, ‘Daddy will be back later.’”

But of course, he wouldn’t be. Kennedy Jr. was at that point too young, Gillon wrote in his book, to “fully grasp the finality of death.” He wasn’t even three years old at the time. “One minute he would tell the agents, ‘A bad man shot my daddy.’ A few minutes later, he would ask them to take him to the office to see his dad,” Gillon noted, heartbreakingly.

Kennedy Jr. grew up with the shadow of his father’s death and legacy always hanging over him. His name didn’t help matters. “Jackie told people she regretted naming John after his father,” Gillon told People in 2019. “She realized it only added to the burden. The irony is that in the effort to honor her husband, she inadvertently made her son’s life more challenging.”

Though Kennedy Jr. appeared to live a life filled with privilege, he was secretly tormented about his position. According to Gillon, Kennedy Jr. once spoke about that directly to him. “He said he was two people. He said he played the role of John Fitzgerald Kennedy Jr., the son of the president,” Gillon told People. “But at his core, he was just John.”

Kennedy Jr.’s inner struggles apparently led him to seek help as he got older. “John was pretty open about his therapy,” Gillon informed People. “There was one day a week where you knew where John was. There were two things John always had scheduled: his massage and his therapy appointment.”

Despite the famous name he bore, Kennedy Jr. worked hard to create a legacy for himself. He led the charity Reaching Up and studied at the New York University School of Law, getting his J.D. degree in 1989. After that, he worked as a prosecutor in Manhattan. And in 1996 – having been secretly engaged for a year – Kennedy Jr. married Carolyn Bessette.

Unfortunately, the marriage supposedly had difficulties from the start, thanks to Kennedy Jr.’s worldwide fame. Bessette-Kennedy hated the lack of privacy she now had as a member of the Kennedy family. Cameras followed her wherever she went, and she was afraid that no matter what job she took, she would be charged with having taken advantage of her celebrity.

While promoting America’s Reluctant Prince in 2019, Gillon also gave an interview to Town and Country. In it, he explained what he had witnessed of the John-Carolyn relationship. It didn’t paint a happy picture. Before they died in the plane crash, Gillon claimed, there were serious problems in the marriage.

Gillon said of Bessette-Kennedy, “The paparazzi treated her horribly. Her life was pretty miserable while she was married to John, and it wasn’t anything that John did. It was because of who he was and what people expected of him.” He went on, “I think she never found her identity as John’s wife. She went from being this vivacious and energetic person, and now she feels captive.”

Gillon reportedly witnessed an incident between the pair not long before they died. Kennedy Jr. had supposedly received a nasty letter about his management of George magazine – and Bessette-Kennedy “just exploded on him.” She wasn’t angry with the writer of the letter, but at her husband for “not fighting back.”

Gillon explained to Town and Country, “That was [Bessette-Kennedy’s] big complaint, that [Kennedy Jr.] just let people walk all over him and he didn’t stand up for himself. She felt that many of his friends were using him and she was trying to push many of his friends out of his life.” And of course, they died before they got a chance to mend their marriage.

Kennedy Jr. did get to fix one relationship before his death, though – the one he had with his sister Caroline. In the months before the plane accident, things were apparently not good between the two siblings. Reportedly, they scarcely even spoke to each other. Gillon looked into the reasons why that was the case.

Gillon told People that Kennedy Jr. had “never liked” his sister’s husband Ed Schlossberg. “John felt like Caroline was dismissive of him, and she didn’t like he was involved with George magazine. But the real tension was with Ed,” Gillon said. Bessette-Kennedy was also part of the discord, reportedly feeding back to her husband that Caroline and Sclossberg thought little of him.

The death of Jacqueline Kennedy in 1994 and the subsequent auctioning off of her possessions made things worse, according to Gillon. “John wanted a private auction, Ed thought that a public auction would raise more money,” he told People magazine. “What John resented was that Ed was making the decision.”

But before he died, Kennedy Jr. apparently decided to reconcile with his sister – and was successful. Gillon talked of that conversation to People. “She was gracious. They agreed they needed to do a better job of staying in touch,” he explained. “John loved Caroline. I think they probably both thought they had time to work it out.”

But, of course, they didn’t. And Kennedy Jr. also didn’t get a chance to pursue what Gillon thinks would have been his calling in life: becoming President of the United States. According to Gillon, as Kennedy Jr. got older and started thinking about his own identity, he decided that “politics was part of his DNA.”

Before Kennedy Jr.’s death, Gillon told People, he was “becoming more comfortable with his political ambitions.” And he had a plan in mind, too. “He wanted to run for governor of New York, and his ultimate goal was to return to the White House,” Gillon claimed. “I think in the year before he died, John planned to be President of the United States at some point.”

The world never got to see what a second President Kennedy would have been like. Gillon seems to think he would have been good, though. During a discussion for the film JFK Jr. – The Final Year in 2019, he mused, “The generosity of spirit is one of the things that really sets John apart.”

Gillon also stated that Kennedy Jr. had always come off as humble, despite his fame and fortune. “John could have lived like a king, but he lived in many ways like the rest of us,” he explained. “He took the subway, he rode his bike, he didn’t ask for special privileges… I think John had humility about him.”

Gillon believes that Kennedy Jr.’s childhood – haunted as it was by the killing of his father and uncle – set the course for the rest of his life. “What I learned was that one of the ways people respond to that type of trauma is to seek out danger,” he told Fox. “Because they realize life can be snuffed out at any minute, they want to live life to the fullest.”

Kennedy Jr. responded to the pain of his childhood by deliberately thrill-seeking, Gillon said. “I think John just always believed something was going to save him, but it just didn’t that night,” the writer explained of the plane crash which killed Kennedy Jr., his wife and her sister. “It’s just one possibility among many.”

While promoting his book, Gillon was asked by InStyle about the famous “Kennedy Curse” – and he was adamant it didn’t exist. Everything that had happened to the family, he thought, was simply human nature. “You know the Kennedy’s are risk-takers. President Kennedy insisted on an open limousine when he is going through Dallas, even though the Secret Service recommended otherwise,” he said.

Gillon went on, “Bobby Kennedy had no Secret Service protection and waded into crowds. And John [Jr.] was reckless. I drove in cars with John. I’ve been in cars while he’s sped down 5th Avenue, weaving in and out of traffic. They took risks and they suffered the consequences of people who take risks. There’s no Kennedy Curse.”

In the course of the various interviews Gillon did to promote his book, it’s apparent that he misses his old friend – even though he vowed to be impartial when writing about him. “[America’s Reluctant Prince] means more to me than any other book I’ve written,” he told InStyle. “I wanted to get it right because John deserved for me to get it right. I had a lot of emotional investment.”

Gillon still has regrets about Kennedy Jr.’s final year. “I got a glimpse of what was going on in his relationship with Carolyn, but I had no idea of the depth of the problems that he was confronting,” he told InStyle. “He never showed it, you would never know. He was just as upbeat and funny and outgoing and full of life as he had been in other times.”

Gillon went on, “I feel bad because I wish I had known. I could have just said something to him or invited him to talk about it, but I didn’t realize how much he was suffering.” But although he is critical at times of Kennedy Jr. in his book, he clearly thought he was a good person who didn’t deserve to die at 38.

When Town and Country asked Gillon what Kennedy Jr. would be doing if he’d survived, Gillon answered, “I want John to be remembered for the life that he lived and not for what he might have become. When you think about John, you don’t have to think about the unfulfilled potential. You can think about the life of dignity that he led.”