They must have looked like a strange group.

Sitting in the cafe of the hip Stanhope Hotel in New York, John F Kennedy Jr — the closest thing the US had to royalty — sat alongside his wife Carolyn and her sister Lauren, with the three holding hands.

For months, the relationship between the most famous couple in America had been quietly disintegrating, their fairytale union shattering behind closed doors.

Lauren, then 34, had arranged the meeting to try and bring the couple back together and at one stage made both husband and wife hold her hands.


Unbeknown to the public, John had been living in the Stanhope, leaving Carolyn to live in their vast Tribeca loft.

Lauren's plan was simple: To get Carolyn to attend John's cousin's wedding.

To ease things along, she suggested she fly with the couple that Friday evening. They could drop her off on Martha's Vineyard and they would continue on to the Kennedy compound in Hyannis Port, Massachusetts.

"Come on," Lauren reportedly urged the warring duo, "it'll be fun." When they finally agreed, the plan was set. "Then I'll see you guys at the airport," Lauren said.

What unfolded next was a devastating tragedy that shook the world. All three of the people sitting at that table would lose their lives in a plane crash. However, how this doomed flight came to pass was a direct result of the last tragic weeks of John's life.

John and Carolyn Bessette were photographed every time they left their home. Photo / Getty Images
John and Carolyn Bessette were photographed every time they left their home. Photo / Getty Images
Shortly after John met Carolyn, he told friends he
Shortly after John met Carolyn, he told friends he "couldn't get his mind off her." Their spark was instant. Photo / Getty Images

The couple instantly became a magnet for the paparazzi, with photographers dogging their every move. Look at shots from that time and it's clear the toll the sudden attention was having on her, with the fun-loving PR usually appearing downcast or taken aback.

While John's entire life had been chronicled by the press, this was a new and deeply uncomfortable ordeal for Carolyn.

"Carolyn got dumped into the deep end of the celebrity thing pretty unceremoniously," friend John Perry Barlow has said.


Still, the couple's romance was progressing apace. On the Fourth of July weekend in 1995, they flew to Martha's Vineyard. There, John took Carolyn fishing where he asked her to marry him.

"Fishing is so much better with a partner," he is reported to have said. The ring was diamond with sapphires and had been given to him by Jackie's partner at the time of her death, Maurice Templesman.

Carolyn reportedly took three weeks to give John an answer as she mulled her future — a life with John would only bring more media intrusion into her life.

Despite this, she said yes.


The love that John and Carolyn had for one another has never been disputed. But their relationship was clearly beset by problems.

In February 1996, they were filmed having a huge row in a New York park, with the pair pushing and shoving each other before JFK Jr sat down on the kerb, in tears.

The following month, according to Vanity Fair, Carolyn called her former boyfriend, model and actor Michael Bergin.

"She seemed to have reached a breaking point," he recalled in his book The Other Man.

"She could only go a few months without seeing me: She needed her fix." (Her friends have disputed Bergin's claims that she was unfaithful to John.)

Despite this, John and Carolyn's secret wedding planning was going full steam ahead. Years earlier, John had found a tiny church on a remote island off the coast of Georgia and it was here, on September 21, 1996, that they tied the knot. The bride was nearly two hours late.

Back home in New York after their honeymoon in Turkey — and now officially a Kennedy — the newlyweds had hoped that the press would grow bored with obsessively hounding Carolyn. John stood on their building's doorstep and pleaded with the assembled media to give his new wife a break.

"This is a big change for anyone," he said to the 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."

Despite his pleas, it was not to be. The paparazzi would continue to stake out their home and chase Carolyn through New York to such an extent that she is said to have feared for her safety at times.

Sasha Chermayeff, a former school friend of John's, told Vanity Fair that after the wedding "everything changed" for the newlyweds. "[The press] just broke her down to the point of real fear and paranoia. Like she wouldn't go out of the apartment," Chermayeff has said.

Fashion insider Fern Mallis echoed this sentiment, telling the documentary The Last Days of JFK Jr that "it was taking a toll on their relationship".

"John's insensitivity was the biggest catalyst of their arguments," Rose Marie Terenzio, John's former PA, claims in her 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 disorganised and clueless as a kid."

Those close to the couple allege communication began to break down early on in their marriage. Photo / Getty Images
Those close to the couple allege communication began to break down early on in their marriage. Photo / Getty Images


According to Michael Bergin, in July 1997, he and Carolyn resumed their affair. He claims they continued to meet up throughout that year and into 1998, everywhere from a motel in Connecticut to Seattle and Los Angeles.

While Carolyn was allegedly finding solace elsewhere, John was dealing with his struggling business.

In 1995 he had launched George, a magazine about pop culture and politics. At first it had been wildly successful, with the first two issues breaking ad sales records. However, three years in, it was still failing to turn a profit and he and his business partner Michael Berman were facing an impending crisis. Should they sell the magazine or find another publisher?

Also straining John in 1999 was the fact his beloved cousin Anthony Radziwill was slowly dying of cancer. The two men had been devoted friends since childhood, with each serving as each other's best man.

"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," Sasha Chermayeff, a school friend has told Town & Country.

By 1999, things between John and Carolyn were at breaking point.

In March of that year, John and Carolyn reportedly entered marriage counselling in a desperate bid to save their union.

"It's all falling apart," Vanity Fair reported John telling a friend. "Everything is falling apart."

The question of children had also become a huge stumbling block. John had already picked out the name he would give his son — Flynn. At some stage in the northern spring of 1999, John moved out of their apartment, checking into the Stanhope.

Of the problems in their marriage, according to Vanity Fair John told the same friend: "I want to have kids, but whenever I raise the subject with Carolyn, she turns away and refuses to have sex with me. 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."

"It sort of went down and down, and by the last year, they were not able to communicate — like not at all," Chermayeff has said.

Others paint a less dire picture of the Kennedy marriage.

"Had he not crashed the plane, it would have been a meaningless few weeks of tension," a close friend of John's has told People, "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 next week they could be right back in love — we'll never know."

"To say their marriage was on the rocks is just inaccurate," Carole Radziwill, Anthony's wife, has said. "Anthony's impending death was a strain on their marriage, no doubt. But it was a difficult time for all of us."

Whatever the true state of affairs, it was in July of 1999 that her sister Lauren arranged that lunch at the Stanhope.

John's cousin Rory Kennedy was set to marry that weekend in Hyannis Port at the Kennedy family compound. John was always going to go but Carolyn's attendance was up in the air.

At her sister's urging, she finally agreed to join her husband and the plan was set: The three would fly together on Friday night.

Maybe this weekend away would help put their marriage back on track.

Whatever the true state of affairs, it was in July of 1999 that her sister Lauren arranged that lunch at the Stanhope. Photo / Getty Images
Whatever the true state of affairs, it was in July of 1999 that her sister Lauren arranged that lunch at the Stanhope. Photo / Getty Images


For both John and Carolyn, their final hours were busy. He was at the offices of George trying to plot out the magazine's future, while she went shopping to Saks on Fifth Avenue, hunting for a dress to wear to the wedding. (She finally settled on a $2,350 Alber Elbaz cocktail frock.)

Late afternoon, John and Lauren left New York City, but hit heavy traffic. When they finally arrived at the Fairfield, New Jersey airport where he kept his plane, it was around 8pm.

Carolyn also arrived later, after having had a long pedicure (by some accounts she made the beautician redo her nails three times to get the colour exactly right).

At 8.39pm, they took off in John's Piper Saratoga, which he technically should have been flying with an instructor by his side. His usual instructor, Jay Biederman, had not been available for that event, so John decided to fly without one.

The evening was humid and there was thick haze. Other pilots had chosen not to take off.

When they failed to arrive, the friend waiting to pick up the couple grew concerned, before alerting the coast guard.

Later, the navy was brought in to help with the 2,500 sq km search. The huge white marquee erected for Rory Kennedy's wedding was instead filled with family members praying, Town & Country reports.

It would later be discovered that the aircraft had crashed about 11km away from Martha's Vineyard where they were due to drop off Lauren Bessette.

"They would love hard, and they would fight hard, but they were very much in love." Photo / Getty Images

"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," Carole Radziwill has said.

"They would love hard, and they would fight hard," friend Ariel Parades, told People. "But they were very much in love."