Only one American high school has produced two presidents of the United States: Phillips Academy in Andover, Massachusetts, known simply as Andover. It was no surprise, really, that people emerged from Andover thinking they could do, or be, anything they wanted, or so the myth went. In my new book, Four Friends, I explore these twin burdens of privilege and expectation through the experiences of four of my Andover classmates, all people of great promise whose lives were cut tragically short. The most privileged and most burdened of them all, of course, was John F. Kennedy Jr., son of an assassinated president, striver, tabloid fixture, quintessential American celebrity, who died tragically, piloting his own plane with his wife and wife’s sister. Below is a part of his story, in the week of the 20th anniversary of his death on the way to Martha’s Vineyard for a summer weekend.
A few days before Jackie Kennedy Onassis died, in May 1994, she wrote a letter to her son John, to be opened only after her death. “I understand the pressure you’ll forever have to endure as a Kennedy, even though we brought you into this world as an innocent,” she wrote. “You, especially, have a place in history. No matter what course in life you choose, all I can ask is that you and Caroline continue to make me, the Kennedy family, and yourself proud.”
For John Jr., her death was scary and transformative. “[He said] things like, ‘Until both of your parents are dead, you don’t really know how alone you are,’” Christiane Amanpour, the CNN anchor, told an oral historian. But John’s friend Gary Ginsberg said he thought John handled death better than anyone he knew. “He lost cousins, he lost parents, and he was incredibly unemotional,” he told me. “Not that he didn’t feel it, but externally was able to hold it together better than anybody I knew. I remember saying, ‘John, how the hell do you do it?’ And he said, ‘You know, I just learned from my family. You just don’t wallow in death. You move on. You hold it inside.’”
Another friend, Sasha Chermayeff, told me Jackie’s death and the deathbed letter further ratcheted up the pressure on John. “It’s a complex thing, right?” she said. “You have this legacy. It’s clear. You can’t ignore it.There’s a lot of pressure. And yet he had enough confidence to sort of want to live out his own life, but he didn’t want to let anybody down.”
On the morning after his mother’s burial, John was back at his desk at George magazine, the political glossy he’d cofounded with Michael Berman in 1993. “He did exactly what Jackie would have done,” a friend told Esquire. “He went back to work.”
Jackie’s death occasioned other changes in John’s life too. Ironically, given Jackie never liked his girlfriend Daryl Hannah, her death was a catalyst for John to move on from her. Soon after his mother’s death, he moved out of Hannah’s apartment on the Upper West Side, back down into a newly renovated loft apartment in an industrial-looking building on N. Moore Street.
Around that time John went to the VIP showroom at Calvin Klein and saw Carolyn Bessette there. A mutual friend thought they would hit it off. The head of public relations at Calvin Klein, Carolyn was a bombshell with an exotic look. He was gobsmacked immediately. “John was attracted to women who were not intimidated by him,” his friend Richard Wiese said. “He liked women with a point of view.” Carolyn grew up in a big, white clapboard house on Lake Avenue in Greenwich, Connecticut, and attended St. Mary’s High School where, in 1983, she was voted the “Ultimate Beautiful Person.” At Boston University she majored in elementary education and appeared on the cover of a calendar, “The Girls of B.U.” After college she did publicity for a few nightclubs in Boston, before being spotted by Calvin Klein and lured to New York to work at his headquarters on West 39th Street.
John first told his friend John Perry Barlow about Carolyn in early 1994. He was still living with Hannah, but he told Barlow that he had met Bessette, and that she was “having a heavy effect on him.” He added that he wasn’t going to “pursue her,” because he was loyal to Hannah. “But it was hard for him,” Barlow said, “because he couldn’t get his mind off her.” Barlow asked John about her and who she was. “Well, she’s not really anybody,” he said. “She’s some functionary of Calvin Klein’s. She’s an ordinary person.”
Barlow met Carolyn in the fall of 1994, after John and Hannah had split. “Carolyn was as charismatic as John was,” he said. “Charisma, you know, was once a theological term meaning ‘grace.’ And she had that. I was also impressed with the fact that she was a bit eccentric. She was not conventional in any sense.” She reminded him of Jackie “in her quirkiness” and in “her unbelievable capacity to engage one’s attention.” Carolyn, Barlow continued, had Jackie’s ability to “be talking to six people at one time, and make everyone feel like the only one in the room.”
Sasha Chermayeff, a friend of John’s from Andover, was also struck by her physical beauty, among other things. “Carolyn was hilarious,” she told me. “She was sarcastic without being mean. She was funny. She was engaging. You cannot tell in photographs how beautiful she was in real life. I never saw a picture of her that did her justice.”
Some two months after John’s friends had been summoned to Martha’s Vineyard for his supposed wedding to Hannah, he was spotted kissing Carolyn at the finish line of the New York City Marathon. They were just there watching the race, but the picture of them together was on the cover of the New York Post, much to the irritation of Michael Bergin, a Calvin Klein underwear model and Carolyn’s on-and-off lover. “Yes,” she told Bergin, when he called her about the picture. “It’s nothing.”
“Nothing!” he yelled at her incredulously, knowing that even he could not compete with John.
Ed Hill, another friend from Andover, said he thought the reason behind John’s attraction to Carolyn was similar to what attracted him to Hannah: that she seemed to be able to handle his fame while at the same time using her own wiles to attract her own attention, thereby taking some of it away from him.
Sometime in the spring of 1995, she moved into John’s loft on N. Moore Street. RoseMarie Terenzio, John’s assistant at George, could tell they were getting serious about their relationship because he always took her call when she phoned the office. His sister was the only other person whose calls he always answered. When some of John’s close friends had taken her measure and decided, for one reason or another, that she was not in John’s league, John wouldn’t hear of it. He was totally smitten.
Over the Fourth of July weekend in 1995, Carolyn and John headed to Martha’s Vineyard. At one point John asked Carolyn to go fishing. While they were out on the water, John asked her to marry him. “Fishing is so much better with a partner,” he said to her. He added that many things in life are better with a partner. He gave her a platinum ring surrounded by diamonds and sapphires, courtesy of Maurice Tempelsman, his mother’s boyfriend at the time of her death. Carolyn did not respond to John affirmatively for three weeks. (The press made it out to be because there were problems in their relationship, but Terenzio, in her book, wrote that was not true; it was more a matter of making sure she wanted to become the wife of John F. Kennedy Jr., and what that meant about surrendering her privacy.)
Bergin confronted Carolyn again about John, and again she said John was “just a friend” who was “going through a difficult time.” And she kept on lying to Bergin about the depth of her relationship with John, despite the fact that they were all living in New York City—Carolyn kept her own apartment, even though she was basically living with John. She would still, on occasion, be with Bergin, a fact that he relayed in his 2004 memoir, The Other Man.
Somehow, though, John and Carolyn managed to keep the explosive news of their engagement under wraps until the Friday before Labor Day. That’s when the New York Post reported their engagement, according to a “good friend” of the couple’s, and for good measure showed a close-up of Carolyn’s diamond-and-sapphire engagement ring.
The following February 25, on an unseasonably warm day, the full range of John and Carolyn’s emotions would be on public display, and unfortunately for them, both were captured by a video photographer for all to eventually see. What started out as an innocent enough walk to Washington Square Park on a gorgeous day, with his new dog, Friday, in tow, turned into a shouting and shoving match ending in tears. At one point, it seemed, John succeeded in ripping the engagement ring he gave Carolyn off her finger.
Carolyn and John’s engagement was news to Bergin, whom Carolyn was still seeing on occasion. In March 1996, she called him up out of the blue. “She seemed to have reached a breaking point,” he remembered in his book. “She could only go a few months without seeing me: she needed her fix.” In April she called Bergin again and said she needed to talk, and invited him to her new one-bedroom Washington Square apartment, even though she was spending most of her days and nights with John on North Moore Street.
They sat on her bed together for a long minute, holding hands and not saying anything. “The reason I came to see you last week is that I was pregnant,” she told him. “I needed someone to talk to.”
“You’re having a baby?” he asked, no doubt recalling that when she had previously become pregnant by him, she decided to have an abortion. “No,” she told him. “I lost the baby. I had a miscarriage.”
Bergin spent the night with her. “I knew it was wrong, and she knew it was wrong, but we both found ways to justify our behavior,” he remembered. He still thought he might have a chance of winning her back. “The way I saw it,” he continued, “she probably didn’t even tell John Jr. about the pregnancy. She had come to me. What did that say about their relationship?” The next morning at seven o’clock, they woke to the sound of one of their mutual friends banging “crazily” on Carolyn’s apartment door. “Get the fuck out of here,” he told Bergin. “He’s on his way over.” John had been trying to reach her, but she had taken her phone off the hook, and so when she continued not to answer, he decided to go to her apartment and see if she was there, having called their mutual friend first to see if he knew where she was. Carolyn was “freaking,” he recalled, and he got “the hell out of there,” carrying his shoes, since he didn’t have enough time to put them on. The next time he saw Carolyn, she was a married woman.
After Labor Day 1996, John’s fellow George colleagues noticed he was having trouble focusing. He was in a good mood, but he was skipping editorial meetings, signing off quickly on story ideas, and leaving the office early. “He was practically whistling through the corridors,” Richard Blow, the magazine’s executive editor, recalled in Vanity Fair. “It could mean only one thing: after about a year and a half of dating, John and Carolyn were getting married. Everyone at George, I think, guessed John’s secret. But no one said a word to him.”
In the end John used every piece of wisdom he had gained through a lifetime of deft media manipulation—both avoidance and charm—to keep his wedding plans secret. He and Carolyn decided to get married at the tiny, whitewashed First African Baptist Church on the northern end of Cumberland Island, Georgia. (He had visited the same church years earlier on a trip with his then girlfriend Christina Haag.) The wedding ceremony occurred at 4 p.m. on Saturday, September 21, 1996. John’s sister was the matron of honor, and her two daughters, Rose, eight years old, and Tatiana, six years old, were flower girls; her son, Jack, three years old, was the ring bearer. Anthony Radziwill, his cousin, was John’s best man. Sen. Ted Kennedy toasted them. The biggest coup of the event, though, was that it had been pulled off without the press knowing. “It was the paparazzi fake-out of the decade,” one magazine concluded.
There was some (misguided) thinking that with John married, and settled down, perhaps the media focus on him and Carolyn would abate. After all, as a newlywed, he was now unavailable, so to speak. But in fact, the media attention on the couple seemed only to intensify, and in a way that began to cause problems both for them and for those around them. Fresh from his two-week honeymoon in Turkey, on Sunday morning, October 6, dressed elegantly in a navy blue suit and red tie, John came downstairs from his North Moore Street loft to the stoop at the front of the building. There was no doorman, and barely a lobby. When he got there he was met, as usual, by a swarm of photographers who always seemed to be charting his every move and those of his new bride. His thought was to charm the photographers by asking for their indulgence when it came to Carolyn. It was a risky ask—after all, the appetite for pictures of them was nearly insatiable. The National Enquirer had reportedly paid $250,000 for the photos of John and Carolyn fighting in Washington Square Park.
He stood on the metal stoop, and in his best aw-shucks voice asked for forbearance. “This is a big change for anyone,” he said to the assembled gaggle. “For a private citizen, even more so. I just ask [for] any privacy or room you could give her as she makes that adjustment. It would be greatly appreciated.” Then he turned around, went back inside, and a few minutes later emerged with Carolyn holding his hand tightly.
John’s plea failed. In December, John nearly “came to blows” with one photographer who trailed after him on the streets of Tribeca. In Hyannis Port one summer, he took a bucket of water and dumped it on a paparazzo’s head. Before Christmas, another time, he confronted the two photographers who had taken the pictures of his fight with Carolyn in Washington Square Park. First he talked to them, then he jumped on the hood of their car—staked out near his apartment—and reached through the roll down window to try to grab the car keys. The incident won John and Carolyn a cover story in the National Enquirer under the headline, “JFK Goes Berserk.” There were the rumors that accompanied the photos. There was one about how Carolyn ran off to Europe to be with her sister after a particularly nasty fight. There were rumors about her infertility, about Carolyn consulting with her lawyer to figure out how to increase the $1.36 million she would be paid if their marriage lasted fewer than three years. She supposedly disliked John’s Brown University friends; he supposedly disliked her expensive shopping sprees. “Carolyn got dumped into the deep end of the celebrity thing pretty unceremoniously,” said John Perry Barlow. According to Chris Cuomo, “She could have never anticipated the intensity that would then be transferred onto her, because now it’s not just, Well, you’re hanging out with this guy that we all care about, it’s, Wow, you’re the one? You’re the one. So it became this combination of everything you would have to deal with if you were dating a rock star, when that rock star also happens to be royalty.”
Complicating matters—whether John knew or not—was the fact that Carolyn had not gotten over Michael Bergin. By April 1997, he had moved to Los Angeles to join the cast of Baywatch, the long-running television series about Los Angeles lifeguards. Shortly after his move, Carolyn had called him and asked him when she could see him again. According to Bergin’s memoir, they began an affair in July 1997 while John was kayaking in Iceland. He claimed the affair continued off and on through the fall of 1997 and spring of 1998, in Los Angeles, in a motel in rural Connecticut, and during a funeral for a mutual friend’s mother in Seattle. According to Bergin, Carolyn seemed desperate and begged Bergin to “save” her from her marriage to John. When they were in Seattle together, “She began to bawl uncontrollably, huge, gasping sobs, so powerful she could hardly catch her breath,” he wrote. “I was getting scared. I was watching her come apart at the seams and I didn’t know what to do.”
He believed that she was asking him “to give her strength” to leave John. In the end he could not do what she wanted him to do. He loved her, yes, but he did not want to be the one responsible for breaking up her marriage. That would be a scandal for the ages, and he did not want any part of it. It was too late for them. He told her no, and eventually left the motel in a cab and returned to his Los Angeles apartment, ultimately refusing her pleas. He never saw her again.
There are those who dispute Bergin’s account of the affair he had with Carolyn after her marriage to John. In American Legacy, C. David Heymann quoted any number of Carolyn’s friends who said it wasn’t true that Carolyn and Bergin had rekindled their affair, and that John was the love of Carolyn’s life. He also poked holes in Bergin’s timeline. It’s hard to figure out the truth. Heymann’s book about John is itself riddled with mistakes. But John’s closest friends believed it was true, whether John could bring himself to believe it or not.
John’s closest friends seemed to know that something was not right with John’s marriage. Ed Hill said Carolyn was complicated; she fit perfectly with what John thought he wanted in a wife, but she was also often more than he could handle. “John inhabited the world of [Calvin’s wife] Kelly Klein’s beach house in Southampton,” he told me. “That wasn’t the only world he inhabited, but it was a big part of his world, and it was a part that he couldn’t avoid because he was the Prince of America. So he needed someone by his side who was, in his words, ‘a player,’ who could navigate that world with him. You could not intimidate her. She could pull rank. She could turn a cold shoulder. She had all the skills. At the end of the day, she was selfish and manipulative and damaged in her own way.”
Sasha Chermayeff said that after the wedding “everything changed” between John and Carolyn. “She got nervous as hell,” she said. “It sort of went down and down, and by the last year, they were not able to communicate—like not at all.” She said Carolyn was “obsessed” with Bergin “being her salvation,” and hoped that she could “go back and kind of pretend” with him that her life wasn’t what it was with John.
It was the pressure of celebrity, and John’s role in it, that made their relationship so impossible. “It just broke her down to the point of real fear and paranoia. Like she wouldn’t go out of the apartment,” Chermayeff continued. “Her excuse—that she was really shut down sexually—wasn’t really true. But she was shut down from him.” Chermayeff said she spoke with John about the fact that his wife wouldn’t sleep with him anymore. He was upset about it. He was in therapy. He may have, eventually, had casual sexual interludes with Julie Baker, a former girlfriend, but he was, Chermayeff said, “very serious, and very seriously committed to the fact that he had fallen madly in love with Carolyn.”
On November 22, 1997, John and Carolyn went for three days to Argos, Indiana, of all places, to the headquarters of Buckeye Industries. A Buckeye executive was dispatched to Chicago and flew Carolyn and John back to the Argos area on a private jet. John had two purposes for the trip: to get his basic flight-instructor rating for the Buckeye, and to trade in his single-seat Buckeye Falcon 582 for a new Buckeye Dream Machine, a powered parachute. Carolyn took her first solo flight in Argos, and she seemed to love the experience as much as John did. “Now you know why we are here,” he told her after she had landed, “to get a two-seater so we can fly together.” They went out to breakfast with the Buckeye executives, who completely fell for John and Carolyn. They especially found Carolyn to be warm and funny—and very pleased to be out of the Manhattan spotlight.
Gary Ginsberg said that for John, flying was a total and necessary release from the unending pressure on him. “He literally wanted an escape from being on the ground, where the pressures on him were so immense,” he told me. “The physical pressures on him in New York City, the constant attention—and the lack of any way to avoid it. Going up in the clouds in the sky was a really important physical escape for him. He talked about that. He talked about the solitude of being in the air. It gave him great comfort, which I think is as much a reason why he wanted to fly as wanting a way to get to the Vineyard. It was a psychological escape for him.” But Ginsberg worried about his friend flying, and whether his mind was sufficiently logical to be a pilot. “He was the most nonlinear thinker I knew,” he continued, “and to fly required an ability to think very logically and very linearly. You’ve got to go down a checklist essentially, and that’s a physical checklist, and that was so not the way John approached problem-solving.”
Over Memorial Day weekend 1999, John and Carolyn went to Red Gate Farm in Martha’s Vineyard (now on sale for $65 million). They were joined by a number of John’s old friends, such as Rob Littell and Chermayeff, her husband, and their son, Phinny. Littell and his wife flew up with John and Carolyn in the new Saratoga plane he had also recently bought, along with John’s flight instructor. John was in control the whole flight. “His landings were barely noticeable,” Littell recalled in his book about John, “something he took pride in. None of us felt nervous about flying with John. He was the opposite of reckless, with the attitude of a cautious and serious pilot.”
At one point as sunset was approaching on Saturday, John decided to go up in his Buckeye Dream Machine, the two-seater version of the flying parachute. He took off from the lawn of Red Gate Farm. “We were all watching,” Chermayeff remembered. They then were going to go to the beach and would meet John after he finished his flight. “He went up, and we saw him have problems, and then we saw him crash,” Chermayeff recalled. “When he crashed he went up and down, and we all went running to him.” The Buckeye had hit a tree that John had tried to avoid, and crumpled to the ground. His foot had been bent backward, and the ligaments in his ankle shredded.
Two days later back in New York City, John had surgery to put a metal plate in his leg. Littell urged John to “slow down”—to take the crash as a sign to cut back on his grueling work schedule, and on the tough job of being him.
John had decided to spend many of the following summer weekends in Martha’s Vineyard to be with his cousin—and best friend—Anthony Radziwill, who had been diagnosed with cancer and knew he was dying. John “wanted to help Anthony just relax that summer,” Chermayeff said. After John broke his ankle, which obviously put a serious damper on his mobility, he waxed philosophical about why he thought it had happened. “He was upset with himself,” Chermayeff said. “But he said he thinks it happened because he’s just meant to sit down in a rocking chair with Anthony and they could just spend the summer, the two of them, just sitting there and not being able to do anything while Anthony died. He kind of immediately saw the good side of that accident.”
John still had a hankering for politics, beyond just editing a magazine about it. In November 1998, Senator Daniel Patrick Moynihan announced that he would retire from the Senate at the end of his term, meaning that a U.S. Senate seat from New York was up for grabs. Many people urged John to run for it. “John immediately started exploring his viability,” Ginsberg told me. He and Ginsberg spoke sporadically about the possibility of John running for the Senate, and studying the numbers to see if it might work. Ginsberg, who had recently left George to be the head of public relations at News Corporation, introduced John to Roger Ailes, the onetime political operative who had created Fox News. “He and I spent a long time with Roger discussing whether he would be viable and how he would put together a candidacy or campaign,” Ginsberg said. “And Roger was very supportive.”
One person who was not particularly supportive of this idea was John’s wife, Carolyn. She continued to shun the spotlight. But it was quickly a moot point. Hillary Clinton effectively thwarted John’s plan to run for Moynihan’s Senate seat by announcing that she was moving to New York and running for it. “John felt like he could not go against her because it would be too disruptive to the state Democratic Party,” Ginsberg said. “He would look disloyal, and he felt like she just outranked him in the pecking order. And for his first campaign, he did not want to go after a sitting first lady. He thought that it would be too bruising, so he decided to drop it.” But he still had not abandoned the idea of entering politics. Instead he just reoriented his thinking. Rather than running for the Senate, he decided he would challenge New York Governor George Pataki in the 2002 gubernatorial election, an idea he discussed with his friends. “John recognized that he was a much more natural executive than he was a legislator,” Ginsberg said.
Other friends of John’s, including Brian Steel, a colleague from the Manhattan D.A.’s office, were aware of John’s serious interest in running for public office. “John said, ‘I’m not going to run,’” Steel told me about John’s decision not to run for Moynihan’s seat. “John is telling me this story, but then he said, ‘You know what? If I had to run for anything, I want to run for governor. Listen, a lot of people from my family have run for office—I think that’s great—but no one’s been a governor. I like being the boss. I like being a CEO. I think I’m better suited to be governor.’” The big unknown was what would happen with Carolyn. “She had to stabilize herself, because she was pretty unstable at that point,” a close friend of John’s told me.
During one of their many arguments, Carolyn had shared with John that she was still sleeping with Bergin. “She threw Michael Bergin in John’s face,” the Hollywood producer Clifford Streit told Vanity Fair. “I think she used Michael Bergin in any way she could to get whatever she wanted out of John. The only one in the world who thought Carolyn would choose Michael over John was John.” John wasn’t sure whether to believe her or not, but what with her mood swings, her drug use, and her extreme reticence, he wanted her to see a psychiatrist. She agreed. In March 1999, he agreed to join her at marriage counseling.
On July 12, Carolyn moved out of their bedroom into a spare room in their loft that John used to store his exercise equipment. John checked into the Stanhope hotel, on Fifth Avenue. It was just down the street from where he grew up.
John spent a lot of time on the phone, contemplating with friends how things had spun so badly out of control. “It’s all falling apart,” he told one friend. “Everything is falling apart.” That afternoon, with his ankle still in a cast, he flew in his Saratoga with a copilot to Toronto to meet a second time with the Magna executives.
On July 14, Richard Blow was sitting in his office at George, which was near John’s, and he could hear John screaming through the closed doors. “In startling, staccato bursts of rage, John was yelling,” he recalled in Vanity Fair. “His yells would be followed by silences, then John’s fury would resume. At first I could not make out the words. Then after a particularly long pause, I heard John shout, ‘Well, goddamnit, Carolyn. You’re the reason I was up at three o’clock last night!’ The shouting lasted maybe five minutes, but John’s office door stayed shut for some time.” For lunch that day, John met Carolyn and her older sister, Lauren, an investment banker for Morgan Stanley, at the Stanhope hotel. Carolyn’s sister thought the get-together would be a good idea to try to clear the air and get the marriage back on track.
At the lunch Lauren also convinced her sister to fly with John that Friday night up to Hyannis Port for the long-scheduled wedding of his cousin Rory Kennedy. In her fit of pique, Carolyn had decided she would not go to the wedding. But of course her absence would be noticed and remarked upon. Even though their marriage was troubled, John wanted to avoid that at all costs, and was desperate for Carolyn to agree to attend the wedding with him. In that regard Lauren played a crucial role, convincing her sister not only to attend the wedding, but also to fly up to Hyannis Port with John in the Saratoga. Lauren agreed to go with John and her sister, even though she was spending the weekend on Martha’s Vineyard, not in Hyannis Port. She convinced John to fly to Martha’s Vineyard, drop her off, then continue on to the wedding. “Come on,” she told them, “it’ll be fun.” John and Carolyn agreed to the proposal. “Great,” Lauren said. “Then I’ll see you guys at the airport.”
But John was still very unhappy. That night from his room in the Stanhope, he was on the phone with a friend, unleashing on Carolyn. “I want to have kids, but whenever I raise the subject with Carolyn, she turns away and refuses to have sex with me,” he told his friend. “It’s not just about sex. It’s impossible to talk to Carolyn about anything. We’ve become like total strangers.... I’ve had it with her! It’s got to stop. Otherwise we’re headed for divorce.” He told the same friend he had even picked out a name for his son—Flynn.
John also was having a difficult time getting along with his sister. There was an ongoing dispute about what to do with the furniture and the significant family memorabilia at the Kennedy compound in Hyannis Port. “There was this battle over all this stuff, and John and Caroline didn’t actually speak for almost an entire year,” said a friend. But that summer, with things between John and his wife becoming increasingly tense, he picked up the phone and called his sister. “They had this really, really good conversation,” the friend continued. “And I knew about it because he told me about it...and all I can say is fortunately for her, because they hadn’t spoken for almost a year.” (Caroline Kennedy declined to be interviewed.)
With a cast off his leg for the first time since Memorial Day weekend, John was hobbling around the George office on Friday, July 16, on crutches. He met with Jack Kliger, his boss at Hachette, to discuss ways to revitalize George. “He and I agreed that there had not been a well-thought-out business plan,” Kliger told the New York Times. “So we said, ‘Let’s figure out how to go forward.’” Kliger said John left the meeting feeling “fairly positive” about the outlook for George.
At around one o’clock John spoke by phone with an employee at the airport hangar in New Jersey, where he kept his Piper Saratoga, confirming that he wanted to fly the plane later in the day, and that he planned to get to the Essex County Airport between 5:30 p.m. and 6 p.m.
As they headed back up to George’s 41st-floor offices, after having lunch together, Blow asked John what he was doing for the weekend. He said he was flying up to Hyannis Port for his cousin Rory’s wedding. “I glanced at John’s foot—even the short walk from the restaurant had tired him—then gave him a skeptical look,” Blow recalled.
“Don’t worry,” John told him. “I’m flying with an instructor.”
“Just don’t crash, okay?” Blow replied. “Because if you do, that speech about all of us having jobs at Christmas goes right out the window.”
“Not to worry,” John said. “I’ll be fine.”
Before he left work, he sent an email to his friend John Perry Barlow. Barlow’s mother had just died. He commended Barlow for being at his mother’s side. He knew something about that kind of loss too. “I will never forget when it happened to me,” John wrote, “and it was not something that was all that macabre. Let’s spend some time together this summer and sort things out.” Barlow did not open the email until later the next day.
John and Lauren Bessette left the George offices and encountered heavy traffic along the way to New Jersey, especially as they made their way through the Lincoln Tunnel. At 8:10 p.m., with the light beginning to fade, John and Lauren pulled into the West Essex Sunoco gas station across the street from the airport. Wearing a light gray T-shirt, John went into the store and bought a banana, a bottle of water, and six AA batteries. When they arrived at the airport a few minutes later, Carolyn was not there. By prior arrangement she was to come to the airport separately in a black sedan.
Where was Carolyn? Following her sister’s intervention at the Stanhope two days earlier, Carolyn had reluctantly resolved to join John at Rory’s wedding in Hyannis Port. On Friday afternoon she went to designer boutiques on the third floor of Saks Fifth Avenue to find a dress that she could wear for the wedding the next day. For $1,640 she found what she wanted: a short black dress by designer Alber Elbaz. From there Carolyn decided to get a pedicure.
At around 8:30 p.m., Carolyn arrived at the Essex County Airport. Moments later she, John, and Lauren climbed into the Saratoga and strapped themselves into the comfortable leather seats. At 8:38 p.m., 12 minutes after sunset, the airport tower cleared John and the Saratoga for departure, and they were off.
John had told Blow that he would be flying with his flight instructor, and not to worry. But in the end, primarily because of how late the hour had gotten, John told the flight instructor he would go it alone. Ed Hill recalled to me: “That night there was a flight instructor. He said to John, ‘You’re taking off late. There’s cloud cover over the Vineyard. Like most Americans I’m willing to inconvenience myself out of my love for you. I will fly up there with you and bring the plane back, or get my ass back to New Jersey somehow. Don’t go without me.’” But John told the instructor to go home and be with his family. He would fly alone. “He did [go alone],” Hill said. “It was magnificently stupid that he did.” According to a subsequent report by the National Transportation Safety Board, John told the flight instructor that he “wanted to do it alone.”
The night was hazy, hot, and humid. And it was difficult to see the horizon as the haze accumulated and the light faded. John had not filed a flight plan with the FAA, nor was he required to do so. He also had not engaged a private tracking service to monitor his flight—nor was that a requirement either. At least one other pilot at the Essex County Airport that night had decided not to fly because of the hazy conditions. Kyle Bailey told Time that he canceled his planned flight because of “a troubling haze that had already reduced visibility,” and that when he “looked off in the distance,” he could not see a familiar mountain ridge. “That is a test that most pilots use at the airport,” he said.
At about 34 miles west of the Martha’s Vineyard Airport, John began to descend at a rate of between 400 and 800 feet per minute, at an airspeed of 160 knots.
At around 9:38 p.m., John turned the plane to the right, heading in a southerly direction. Thirty seconds later John leveled the plane out at an altitude of 2,200 feet and began a climb that lasted another 30 seconds. At 9:39 p.m. the plane leveled off at 2,500 feet and headed in a southeasterly direction. About a minute later John climbed the plane to 2,600 feet and made a left turn, and then began descending at a rate of 900 feet per minute. “For nearly five minutes the plane’s descent continued at this relatively steep rate, losing about two-thirds of its altitude until it was just 2,300 feet above the Atlantic wavetops,” Jeff Kluger and Mark Thompson wrote in Time a few days later. “Martha’s Vineyard was by now only 20 miles away, but if the Piper kept dropping at this rate, it would hit ocean well before it reached the landing strip. For a pilot flying in better conditions—even an inexperienced pilot—the next step would be obvious: look out your window, get your bearings, and level out your plane. JFK Jr. didn’t have that option. No matter how low he flew, there was still haze. Kennedy, who had earned his pilot’s license only 15 months ago, now found himself flying a plane that might as well have had no windows at all. The first rule pilots are taught, in a vertiginous situation like this, is to ignore the signals your body is trying to send. The inner ear is equipped with an exquisitely well-tuned balance mechanism, but it’s a mechanism that’s meant to operate with the help of other cues, particularly visual ones. Without that the balance system spins like an unmoored gyroscope.”
Then John, increasingly disoriented, turned right; the speed of the plane increased, and it was descending rapidly, at a rate of 4,700 feet per minute. “Perhaps he was still searching for a break in the haze, or perhaps merely stumbling about,” Kluger and Thompson continued. “If he followed his flight training—and his reputation as a generally cautious pilot suggests he would have—he would now have performed what’s known as ‘the scan,’ a quick survey of half a dozen key instruments that would reveal his plane’s altitude, attitude, and direction. But his brief experience with instrument piloting—he was certified to fly only under eyeball conditions—left him ill-equipped to handle a confusing situation.
As the dials on the panel and the signals in his brain told him two different things, his eyes probably bounced back and forth between the instruments and the windows in a frantic attempt to reconcile the two. ‘He was like a blind man trying to find his way out of a room,’ a Piper Saratoga pilot surmises. And like a blind man, he now completely lost his way.”
