Inside the Heartbreakingly Tragic Final Days of John F. Kennedy Jr.: Family Strife, Financial Woes and Talk of Divorce

In Britain, they have the royal family—a centuries-long lineage that offers scandal, ignominy and deadly rivalries aplenty that can fill both a library’s worth of historical biographies and enough petty rumor and innuendo to leave millions wondering if Kate Middleton and Meghan Markle really are getting into heated shouting matches in the halls of Kensington Palace. 

America, having rejected a monarchy of its own, has the Kennedys. A powerful political dynasty with seemingly endless branches that extend from the White House to Hollywood, the family’s history is chock full of shocking deaths, fascinating mysteries and relationships both deliriously enchanting and tragically destructive. 

And for a period in the ’80s and ’90s, the undisputed prince of Camelot was John F. Kennedy, Jr. Blessed with the dashing good looks and undeniable charisma of his parents, President John F. Kennedy and Jackie Kennedy Onassis, People‘s 1988 pick for Sexiest Man Alive intrigued the nation as he romanced the likes of Brooke Shields, Sarah Jessica Parker, Cindy Crawford and Daryl Hannah. 

But when the lawyer turned magazine editor first connected with statuesque Calvin Klein publicist Carolyn Bessette in 1994, he was the one left entirely captivated. 

Their Fourth of July engagement on Martha’s Vineyard the following year was the stuff of romance novels, but behind the scenes, the blonde beauty made the political scion work to earn her hand in marriage. “She held the proposal off for about three weeks,” a close friend revealed to People last year, “which I think just made him all the more intent on marrying her.” 

Which he did, little more than a year later, whisking her off to Georgia’s Cumberland Island for a top-secret ceremony at the First African Baptist Church, the eight pews holding such notables as Onassis’ sister Lee Radziwill, John’s uncle, Senator Ted Kennedy and his sister, matron of honor Caroline Kennedy Schlossberg. The pair sliced a vanilla buttercream-frosted cake, danced to Prince and made headlines, most notably for the bride’s simple bias-cut Narciso Rodriguez slip dress that transfixed the nation. 

Of course, the fairytale didn’t end with the duo living happily ever after. Not even three years later—on July 16, 1999—the single-engine Piper Saratoga John was piloting to the wedding of his cousin Rory Kennedy on the family’s Hyannis Port compound slipped off the radar. After a five-day search, that left President Bill Clinton fielding criticism for expending resources to find what were essentially three private citizens, the wreckage was discovered, the bodies of John, then 38, Carolyn, 33, and her sister Lauren Bessette, 34, still inside. 

“It was earth-shattering. It was unbelievable. It was as if the earth had cracked in half somehow,” ABC News Consultant RoseMarie Terenzio, at the time John’s assistant at his magazine, George, shared in the network’s documentary, The Last Days of JFK. “And I could not understand how this could happen to him of all people.”

Thursday night’s special, the first in what is sure to be many memorializing the 20th anniversary of the tragedy, covered the anxiety of his final days on earth, as John looked to shore up the financial future of George, a passion project that was hemorrhaging advertising dollars and dealt with the paralyzing, non-stop attention on his young marriage.

But through interviews with longtime friends, and previous girlfriends, the program also provided a peek at the burden of growing up one of the world’s most famous political scions and how the NYU law school grad dealt with the assassination of his father, just days before his third birthday in 1963, and the subsequent killing of his uncle Robert F. Kennedy. 

“You can’t really imagine what it would do to a young person to have both his father and his uncle murdered in the same way,” After Camelot author J. Randy Taraborrelli shared in the documentary. “For John, I think that it made him feel that you can’t waste a moment because he didn’t know how long he was going to be here.”

The answer, of course, was 464 remarkable, world changing and yet oft-troubled months, the last of which proved to be particularly stressful. 

The second coming of JFK and Jackie, John and Caroline, a 5-foot-10 native of Greenwich, Conn. who was as worldly and au courant as she was beautiful, were the toast of New York City and pretty much any town they visited. As tabloids breathlessly documented every black tie event they attended, every move they made, the public waited eagerly for the moment little John John would announce that a heir was forthcoming. Instead, the prevailing noise from the couple’s camp was a constant stream of rumors that they were on the verge of a split. 

“John’s insensitivity was the biggest catalyst of their arguments,” Terenzio detailed in her 2014 book Fairy Tale Interrupted. “Carolyn would decline invitations from friends because John said he was coming home for dinner. So she would wait and wait and wait, while he worked late and went to the gym, and then waltzed into the apartment way past dinnertime…Another classic scenario was when he would spring important information on her at the last minute, such as ‘Oh, by the way, the Whitney benefit is in two days’ or ‘I’m bringing a friend home for dinner…right now.’…It wasn’t mean-spiritedness on his part. He was simply as disorganized and clueless as a kid.”

His fame also proved troublesome for Carolyn. From the moment the couple returned from their 1996 honeymoon, they were met with a swarm of photographers outside the front door of their apartment in Manhattan’s upscale Tribeca neighborhood. John pleaded with them to give his wife space, allow her to become accustomed to this new upper echelon of notoriety, but it was to no avail. Photos of the compelling blonde former model appeared everywhere with the likes of Vogue and Harper’s Bazaar clamoring to get her to pose for their covers. 

“John loved Carolyn, he was enchanted with her—body and soul—from the first minute he met her,” his friend Brian Steel, a fellow assistant DA in the New York County District Attorney’s office told People. “But I think the fact that she had trouble coping with his fame definitely caused stress later on.”

As she sought refuge at the West Village apartment of her close friend, designer Gordon Henderson, John struggled with her inability to adjust to his world. “She needed to work through that, but he never wavered in his commitment to helping her,” Steel told the mag, instead focusing on what he saw as a blessed future. “He definitely wanted children at some point in time. He loved kids. He loved his nieces and nephew. And they were very much life partners.”

But in the final weeks of their lives, the pressure of the spotlight had intensified to the point were Carolyn “felt cornered” by the photographers and reporters that lurked outside their place, John’s friend John Perry Barlow told People. 

Compounding that further was George‘s financial strain—John was in the process of looking for a buyer for the magazine, created in 1995 to blend his two worlds of celebrity and politics—and the pain of caring for Anthony Radziwill, John’s 40-year-old cousin, who would succumb to cancer mere weeks after the duo’s accident. As John worked to craft the eulogy he intended to deliver at the funeral, Carolyn would make nightly trips to the hospital, bringing Anthony his favorite soup from New York establishment Il Cantinori and his wife Carole Radziwill, comfort. 

“To say their marriage was on the rocks is just inaccurate,” Carole, who would go on to tell the story of the cousins’ bond in her memoir What Remains before finding further fame on The Real Housewives of New York, told People. “Anthony’s impending death was a strain on their marriage, no doubt. But it was a difficult time for all of us. If it weren’t, we would be inhuman.” 

Difficult was one thing, but as Edward Klein detailed in his 2003 book The Kennedy Curse: Why Tragedy Has Haunted America’s First Family for 150 Years, the pair’s connection had devolved to the point that that days before the crash John phoned a friend to vent about his flailing marriage, complaining that whenever he broached the topic of kids, Carolyn “turns away and refuses to have sex with me.” And their bedroom activities were just one piece of the issue. The pal would later recount to Klein the words that John told him that day. “It’s impossible to talk to Carolyn about anything. We’ve become like total strangers,” he reportedly said. “I’ve had it with her! It’s got to stop. Otherwise we’re headed for divorce.” 

At that point, the pair were living apart, according to Klein, with John crashing at the Stanhope, a hotel located across from the Metropolitan Museum of Art on New York’s tony Upper East Side. As such, Carolyn was none too eager to play happy couple by turning up on John’s arm at a family wedding and she was especially uninterested in allowing him to fly them there in his $300,000 six-seater plane.

John had first entertained the idea of flying when he was studying at Brown University—a hobby that his mother had found particularly troubling, with Klein writing she had made him promise he would never pilot a plane solo, reportedly pleading with him, “Don’t we have enough deaths in the family from plane accidents?” 

He went on to take lessons from Flight Safety Academy in Vero Beach, Fla., posing with his instructors post-graduation and inscribing the photo with a message that now reads as eerily prescient: “To Flight Safety Academy, The bravest people in aviation because people will only care where I got my training if I crash.” 

Thursday, the day before what would be his last flight, he made a stop at Lenox Hill Hospital to see his orthopedic surgeon and have a cast removed from the ankle he’d broken six weeks earlier in a paragliding crash—a move that meant he could at long last fly without the aid of a co-pilot. So the fervent baseball fan was in an especially good mood when he joined lawyer pal Gary Ginsberg in owner George Steinbrenner‘s field-side box at Yankee Stadium that evening.

Still, the accident had given some friends pause, with Barlow reportedly remarking to his pal that he was overly confident in his aviation skills, knowing “just enough to be dangerous.” Because while John held a pilot’s license, he was some 10 hours short of getting his instrument-rating certification, a fact that would later make people question why he was flying alone at night in the first place. 

But without the benefit of hindsight, most of the couple’s friends and family just thought of it as another chance for John to take to the air doing something he’d truly grown to love. Lauren, especially troubled by the couple’s decision to live separately, had arranged a meeting for the three of them to get drinks in the Stanhope’s café on the Wednesday before the scheduled trip. Holding her sister’s hand, the Morgan Stanley executive director urged her to accompany John to Hyannis Port, Klein wrote, offering to fly with them so she could spend the weekend with friends on nearby Martha’s Vineyard. According to Klein, her sales pitch was simple: “Come on, it’ll be fun.”  

The couple agreed to her proposal. 

“Carolyn decided to be with his family that weekend in the Cape—to be together,” a close friend of John’s told People. “And she would be with him in a safe and private place. That’s what family means. And that meant something.”

So by all accounts, that Friday, July 16, John was feeling particularly upbeat as he maneuvered through George‘s midtown office with just the use of a cane. He met with the magazine’s publisher, Hachette Filipacchi president Jack Kliger, about obtaining further financing, sharing details of the meeting he’d had the weekend before when he’d flown to Toronto, with the help of a co-pilot, to court potential backers. Staffers say the negotiations left John in good spirits and with enough time to make a quick trip to the gym and fire off an email to pal Barlow, a former lyricist for the Grateful Dead, who had recently lost his mother. 

At about 6:30, Lauren made the brief walk over from her office and the pair climbed into John’s white Hyundai convertible to make the drive out to New Jersey’s Essex County Airport. The normally 40-minute trip took an hour-and-a-half with rush hour traffic clogging the roads.

But the pair still arrived before Carolyn, who was running late after a shopping trip to Saks to choose a $1,640 Alber Elbaz dress for the wedding and an exceptionally long pedicure, the style icon exacting in her determination to have her polish match a light lavender swatch she had brought along. John, still limping slightly, had time to pop into the West Essex Sunoco station just across the street to pick up some travel necessities: three bananas, some water and a pack of AA batteries. Finally Carolyn arrived by chauffeured sedan and before taking to the air, placed a phone call to Carole. 

“I don’t remember anything really important from that conversation,” Carole revealed on an episode of HLN’s How It Really Happened with Hill Harper. With the exception of one exchange at the end. “She said, you know, ‘I love you.’ And for some reason, I didn’t say I love you back. And that always stuck with me.” 

The trio took flight at 8:38 p.m. heading east into a sky hazy enough that fellow pilot Kyle Bailey was widely quoted as telling his family, “I can’t believe he’s going up in that weather.”

By 10:05 p.m., air traffic control on Martha’s Vineyard, where John was to have dropped off Lauren before continuing on to Hyannis Port, radioed that the plane had failed to complete the relatively brief 200-mile trip. 

Radar information showed that John began a descending from 5,600 feet to 2,300 feet some 34 miles from the island into decreasing visibility. Dr. Bob Arnot, an NBC News medical correspondent who was piloting himself to his Nantucket vacation home told Newsweek he had made the same route along the Connecticut shore not 15 minutes earlier, and when he began to drop down, he was surprised when he couldn’t spy the lights of Martha’s Vineyard: “When I went through that corridor, I couldn’t see anything at all. It was murky black.” 

While it’s unknown exactly what happened in John’s final minutes, radar data showed him making an unexpected climb some 20 miles from the island, correcting himself and then making another right turn off-course where the plane began to plunge at a rate of nearly 100 feet per second. With John already so close to the water he would have been left with little time to level the plane off. Experts estimated the dive would have lasted no more than a half a minute. 

When the bodies were found 116 feet below the water’s surface on July 21, the splash point determined to be just off the tip of Martha’s Vineyard near a private beach Jackie had left for her children, they were upside-down, but still strapped to their seats, an autopsy showing they had all died instantly on impact. 

Following John’s wishes to be buried at sea, the trio was cremated, their ashes placed in Tiffany-blue boxes and scattered by family members off the coast of Martha’s Vineyard July 22 as a crowd of tourists and locals looked on and members of the Navy worked to keep press helicopters at least 10 miles away from the destroyer Briscoe as it sliced through the Vineyard Sound. 

The next day, Sen. Ted Kennedy delivered the eulogy at a small private service at St. Thomas More on Manhattan’s Upper East Side, the elegant church where John’s mother once worshiped, cementing the final, tragic end to the pair’s all-too-brief love story. 

Those close to the duo agree it was a romance laced with much passion and fire. “They would love hard, and they would fight hard,” Ariel Parades, whose grandmother Providencia Parades served as an assistant to Jackie, told People. “But they were very much in love.” 

And if their dearest friends’ predictions proved true, they were to remain that way. 

“Had he not crashed the plane, it would have been a meaningless few weeks of tension,” one pal of John’s insisted to the magazine, “but it took on a life of its own because it was the last chapter of their life. One week they could have been at war, and the the next week they could be right back in love—we’ll never know.”