The Last Days of John F. Kennedy Jr. and Carolyn Bessette Kennedy

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.

By Adrienne Gaffney Published: Jul 15, 2024 10:58 PM EDT [townandcountrymag.com]

After the dinner, held at the Washington Hilton, the group made their way to an afterparty hosted by Vanity Fair. “It was this exclusive celebrity political event, and they were the stars of the show,” says Terenzio. “Everyone stopped and turned around as they walked in.”

This was a time. George had to be figured out; John’s cousin is dying. Maybe Carolyn has to decide how she wants to live her life. That’s when the accident happened.

It was there that one of the most famous images of the couple was taken. John’s blazer is off, and Carolyn is nestled on his lap. In one frame he is whispering in her ear, in another he is kissing her. All the questions that dogged them—about their marriage, about her deep distrust of the media, about his future and where it would take them—seem far away. They are a couple at ease and in love, content and relaxed. They fit together.

It’s impossible to know whether this photo is the truth about John and Carolyn or simply a happy moment caught amid the swirl that followed them everywhere. Despite their golden couple status, in the summer of 1999 John and Carolyn were at a crossroads. They were facing careers in flux, the ups and downs of the early years of marriage and questions about children—and, most poignantly, the final days of a close loved one, John’s cousin Anthony Radziwill.

“This was a time,” says Matt Berman, the creative director of George and a close friend of the couple’s. “George had to be figured out; his cousin’s dying. Maybe Carolyn has to decide how she wants to live her life. Does she want to work? Does she want to have kids? Does she want to lead charities?”

“Here you are in the middle of a shift like that, and that’s when the accident happened.”

The choices they might have made—and the answers they might have found—were rendered forever unknowable on July 16. On that hazy Friday evening, John took off in his small private plane from New Jersey’s Essex County Airport, with Carolyn and her sister Lauren Bessette, 34, as his passengers. Before they reached their destination on Martha’s Vineyard, the plane crashed, killing them all.

Those who knew John and Carolyn as a couple describe a warm pair who brought together unlikely acquaintances and welcomed all those around them, from fashion types and schoolmates to George colleagues at all levels and highbrow celebrities like John’s longtime friend Christiane Amanpour. John was compulsively busy; in addition to his hands-on role at George, he had numerous Kennedy family obligations. They traveled (that spring to London for the opening of Ralph Lauren’s new boutique) and had cozy weekend get-togethers with family on Martha’s Vineyard.

Living in a loft on North Moore Street, they were icons of Tribeca, which was midway through a transition that would take it from commercial zone to New York’s wealthiest zip code. Both John and Carolyn were regularly spotted on the cobblestone streets with their dog Friday. They helped popularize neighborhood restaurants like the Odeon and Bubby’s, both of which have become downtown institutions.

But beneath the surface, John and Carolyn were dealing with a heart-wrenching crisis. In early 1994, Anthony Radziwill had been diagnosed with a rare sarcoma. (The news came within weeks of Jackie Kennedy being diagnosed with non-Hodgkin’s lymphoma, which would take her life just months later.) Anthony and John were very close. The son of John’s maternal aunt Lee and Polish prince Stanisław Albrecht Radziwiłł, Anthony was nearly the same age as John and the only male cousin on Jackie’s side of the family. The two were like brothers, serving as best man in each other’s weddings.

Over the course of his illness, Anthony underwent surgeries, chemotherapy, and experimental treatments; always by his side was his wife Carole, a fellow producer at ABC News whom he married in 1994. But by 1999 it was becoming clear that Anthony would not recover. “The summer of 1999 was very difficult for all of us,” Carole remembers. “We knew that it was likely Anthony would not survive to see Labor Day, and we were all on edge, not knowing what to do or say. We were all doing our best to keep smiles on our faces.”

Those who knew John saw the impact that Anthony’s illness had on him, particularly in 1999. “That was a very painful year [for him], to watch someone he’d grown up with, who was exactly his age, and he’s dying and it’s really hard on his wife, his sister, his mother,” says Sasha Chermayeff, an artist and longtime friend who first met John when she and he both transferred to Phillips Andover Academy as juniors. “For John, I think that Anthony’s illness brought everybody closer in a good way, including Carolyn and him.”

Carolyn too was deeply affected by the ordeal the Radziwills faced. She and Carole had made an immediate connection—each had gone from a teenage job behind the counter at a Caldor department store to marrying royalty, one figuratively, one literally. Their relationship deepened over the course of Anthony’s illness. “We grew very close, often spending day after day at various hospitals together,” Carole remembers. “I spent only five years with Carolyn before her death in 1999, but we went through a lot of real life stuff in that short time.”

John might have turned to work as a welcome distraction, but his professional life was also in something of a crisis. When he launched George in September 1995, with a Herb Ritts cover photo of Cindy Crawford outfitted as George Washington, the magazine had been a hit. Kennedy’s name and mystique gave George access to talent that most upstart publications could only dream of. Madonna contributed to the first issue, and covers featuring Kate Moss and Barbra Streisand landed with a splash. Having America’s most eligible bachelor at the helm created a built-in audience, and the first two issues broke records for ad sales in a new publication.

The magazine’s purview was the intersection of politics and pop culture, and it aimed to introduce smart, savvy political coverage to an audience that was often bored by the topic. “John’s basic conceit was we’re living in a world where, like it or not, pop culture and politics are merging, and if you treat politics as part of the pop culture and politicians as celebrities, you might bring more people into the tent to become interested in politics,” says literary agent David Kuhn, a friend of John’s who had worked as an editor at Vanity Fair and the New Yorker and consulted on the launch of George. “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.”

But the magazine, however prescient, missed its goal of being profitable within three years, and ad rates dropped in later years. By 1999, John and his collaborators faced difficult choices about the future of their enterprise. “I think what was stressful was that we were at a growing pains point,” says Berman, author of JFK Jr., George, & Me: A Memoir. “What was going to work for us? Are we going to be better in a big corporation? Is it more of an independent project? Should John find funding and we do it on our own?”

Kennedy’s corporate partner in George had been French publisher Hachette Filipacchi, which was reportedly considering pulling funding for the magazine. John was spotted in meetings with executives like Conde Nast’s Steve Florio, and he had flown to Toronto the week before his death for a meeting about a potential partnership with Canadian investors to buy out shares of George.

In the Spring of 1999, Hachette got a new American CEO, Jack Kliger, which put John on even shakier footing with his corporate partner. Kliger, however, disputes the idea that Hachette had stopped believing in George, insisting now that he was working with Kennedy in good faith to keep the magazine alive. “It was not making money at that point, and the trend lines were not heading the right way in terms of revenue growth versus cost growth,” Kliger says. “He understood all of that, and he wanted to figure out an alternative plan, which I said I was prepared to put forth to the corporate parent in France. We were working on that effectively, and then history cut us short.”

Kliger says Kennedy canceled a meeting with him that had been scheduled for the afternoon of the day he died, explaining that he was going away for the weekend but that he intended to meet with Kliger in the coming week.

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.

During the press conference for the launch of George, Newsday reported that Carole Radziwill had been mistaken by a reporter for Carolyn. “She wouldn’t be caught dead here,” Radziwill told the paper.

In 1999, Carolyn Bessette Kennedy was facing her own professional crossroads. When she and John had begun dating, two years before their 1996 wedding, she was working for Calvin Klein. Though she is frequently described as a golden girl from Greenwich, Connecticut, she was scrappier than that reputation implies. Her parents had divorced when she was very young, and Carolyn and her twin sisters, Lisa and Lauren, had been raised by their mother Ann Freeman, an educator, and her stepfather Richard Freeman, a surgeon. Carolyn attended Boston University, where she had supported herself with part-time jobs. “She always worked,” Colleen Curtis, who roomed with Carolyn in college, told T&C in 2016. “Always.”

She had risen from a retail job at the Calvin Klein boutique in Chestnut Hill, Massachusetts, to a rarefied role in the company. “I’ve been doing this for 40 years now, and there are probably five or six people who stand out,” says Neil Kraft, who worked as creative director at Calvin Klein in the ’90s. “This had nothing to do with the Kennedys. I couldn’t care less about that. But she was one of those people who stood out at Calvin just as a force.”

Sam Shahid was an art director who worked with Carolyn on photo shoots by Calvin’s then-wife, Kelly Klein. He recalls bumping into her often at restaurants like Il Cantinori, where she would dine discreetly with friends like designer Narciso Rodriguez. “When Carolyn walked into the room, you always knew she was there, the presence. I think Calvin just worshiped her as far as the style. He really depended on her for her taste and her style and her ideas and music,” Shahid says.

By the time Carolyn married John, she was no longer working for Calvin Klein, and the frenzy that followed her everywhere made it difficult to imagine her ever working in a traditional office again. The paparazzi were merciless in their pursuit of her, staking out the Tribeca apartment and following her through the streets of the neighborhood so doggedly that she feared for her safety.

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. The tabloids had rushed to label the statuesque blonde an ice princess, somehow unworthy of America’s favorite son, and her reticence led many to conclude that she was remote and humorless.

The truth, according to her friends, was far different. “She had this amazing sense of humor, really sharp and funny,” Berman says. “For the most part no one really knows what she sounded like or talked like or what kind of woman she was. I found her very down to earth, very funny, very supportive of her friends, very caring. All the things that you don’t see in a picture.”

Berman and other George staff members say Carolyn treated them like family, visiting the office and frequently hosting them at home. She also maintained a close knit group of friends that included Narciso Rodriguez, who had designed her wedding dress; Paul Wilmot, a PR executive who was her former boss; designer Gordon Henderson; stylist Joe McKenna; Kelly Klein; Marci Klein; and casting agent Jessica Weinstein. They followed her lead and never spoke to the media about her.

Carolyn’s favorite phrase was, ‘We need to talk.’

At a memorial mass at New York City’s St. Thomas More Church on July 23, Hamilton South, one of her closest friends, delivered a eulogy that reflected on Carolyn’s tremendous capacity for friendship. “Her favorite phrase was, ‘We need to talk.’ That would be the beginning of a two- or three-hour telephone odyssey, a tour of Carolyn’s horizon that revealed a range of interest that left you spinning—from this new book to that museum, from fashion to Walt Whitman, from what’s in the paper to what’s up in town. She could be highbrow and low-down. It left you breathless, exhausted, and hungry for more,” he said.

“To spoof herself, and to cover up what she was really doing, she’d say in these talks, ‘Now let’s remember, it’s all about me.’ She made it the permanent subject line in her e-mail: ‘It’s about me.’ But that was just another of her secrets—it was ­never about her. When you talked to Carolyn it was all about you, and all about life.”

In his remarks, South also said that Carolyn had a professional dream of creating documentaries that would focus on people facing challenges, working out of a small office in Tribeca.

Work was reportedly not the only thing troubling her. Several books and articles published since their deaths have claimed that John and Carolyn were in a difficult patch in their marriage; there were claims that both had been unfaithful. “Three years into the marriage things were really problematic,” says Kennedy’s good friend Sasha Chermayeff. “I know that they really did love each other. It was not a lack of love.”

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.

Other friends speak of a normal couple weathering the turbulence of a new marriage. Another close friend disputes reports of serious relationship woes and says that the two were working with a realtor to find a second home outside New York and thinking about having children.

As the calendar flipped to July, both John and Carolyn were doing their best to live their lives, despite Anthony’s declining health and the questions looming around George. Carole and Anthony Radziwill had just moved into Red Gate Farm, Jackie’s home on Martha’s Vineyard, so he could spend his last summer in a serene environment.

John was recovering from a broken ankle, an injury he got in a paragliding accident over Memorial Day weekend. A lifelong athlete who used exercise as one of his main forms of stress management, John would surely have been eager to be free of the cast. He had maintained his breakneck schedule while on crutches, but his limited mobility would have had a profound affect on his mood.

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.

John had had a fascination with aviation since his early childhood, when he would watch his father’s helicopter touch down on the White House lawn. He pursued flying intermittently over the years, becoming more serious about it only after the death of his mother in 1994. (She reportedly disapproved of her son flying, perhaps partly due to her stepson Alexander Onassis having died in a crash in 1973.) John enrolled in a Florida school in early 1998 and received a private pilot’s license that April.

Friends had been concerned about Kennedy’s interest in flying, but it fit with his enthusiasm for other adventurous pursuits, such as extreme kayaking, scuba diving, and, yes, paragliding. Chermayeff says she saw the appeal to John of piloting himself, as traveling via public airports left him uniquely vulnerable to crowds.

“It’s one thing when you’re in a restaurant and people come up to you. You can sneak out the door when you’re done and get in a cab and end up in a different place. But he hated the airport, because he was always so stuck,” she says. “He was just like, ‘I have to sit there,’ and one person after the next is just going to come up to him. He was too nice to be ruthless about it, so he loved flying, and he loved that little airport.”

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.

John typically made weekend flights to Massachusetts with his instructor, Jay Biederman, but Biederman was unavailable that Friday night. John chose to forgo taking another pilot. When his Piper Saratoga, which he had purchased less than three months earlier, took off from New Jersey at 8:39 p.m. on July 16, it is likely that it was John’s first time making the trip alone in his new plane. John and his passengers took off later than they had intended, and there was a thick haze that night that limited visibility; other pilots had decided not to fly.

When the plane did not arrive as scheduled, Dan Samson, a longtime friend who had planned to pick up John and Carolyn, became alarmed. He checked in with the Radziwills to see if there had perhaps been a change of plans, which ignited a ping-ponging of frantic phone calls as friends and family tried to locate them.

Eventually the coast guard and navy were brought in. The search would extend across more than 1,000 square miles and last five days. It became apparent that the plane had crashed seven miles off Martha’s Vineyard a little more than an hour after departure. Rory Kennedy postponed her wedding; the white tent that had been meant to house a reception for 275 guests was used instead as a site for family to gather and wait and pray. (Rory and her fiancé married three weeks later in a small private ceremony in Greece.)

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. There were also questions about his decision to fly solo and the fact that his ankle was not fully healed.

“It was so upsetting to me that he flew that night when he had just gotten his cast off,” says Chermayeff. “He wasn’t fully instrument trained; he shouldn’t have done it. It was a pilot negligent mistake in which he died and two people died with him. I have nothing but sadness about that.

Richard Weise, a friend and fraternity brother of John’s from Brown who is the son of a pilot and flies himself, had mentioned to John right after he got his pilot’s license that he subscribed to a publication about climbing accidents. “I said I read it because I want to learn from other people’s mistakes. And he said, ‘Oh, you’re just trying to discourage me,’ ” Weise says. “That was probably what he didn’t get, that whole idea of learning from other people’s mistakes.”

“To be honest, I wasn’t surprised [by the crash]. Clearly he was flying in a plane that he was not trained or equipped to handle. I think he had many great qualities, but attention to detail was not one of them.”

During a week of memorials in New York and Greenwich, John, Carolyn, and Lauren’s ashes were laid to rest in the Atlantic Ocean following a Catholic service held on a navy ship. Coverage at the time noted that being at sea made it one of the few moments in John’s life when cameras were unable to intrude.

No one in the Bessette family has ever spoken publicly about the loss of two daughters. A year after the crash, Carolyn and Lauren’s mother Ann Freeman released a statement through her lawyer. In it she said, “The loss of these three young people whom we loved so much has forever changed our lives. We continue to struggle with our grief, and we choose to maintain what’s left of our privacy.”

Three weeks after the funeral, Anthony Radziwill, who had recited Psalm 23, “The Lord Is My Shepherd,” at his best friend and cousin’s memorial, died in a hospital in Manhattan. He was buried in East Hampton. Caroline Kennedy delivered a eulogy; her brother had already begun to write one, which he never got to give.

Carole Radziwill understands better than anyone that there is no way of knowing where John and Carolyn would be today, but she has imagined it frequently over the years. “I’d like to think John and Carolyn would have lots of kids. I know they both wanted that. I imagine the tabloids would eventually tire of them and leave them to live in peace. John’s magazine, George, would be a spectacular success story. But that’s the thing about young deaths: You don’t only mourn what was, you also mourn what could have been.”