When a plane carrying John F. Kennedy Jr and his glamorous wife Carolyn Bessette plunged into the sea off Massachusetts, it only fuelled America’s fascination with the tragic Kennedy clan. As their story makes its way to the screen – in Love Story, starring Naomi Watts, Paul Anthony Kelly and Sarah Pidgeon – we uncover the truth of this fiery American romance.
It was July 16, 1999. A balmy midsummer Friday evening. The Kennedy clan was gathering at the family compound in Hyannis Port, the storied New England coastal retreat where, in November 1960, John F. Kennedy found out he was going to be the 35th President of the United States. It was also where members of America’s most famous political dynasty had regularly played bruising games of touch football, demonstrating their vigour and competitiveness.
The youngest daughter of the late Robert F. Kennedy, Rory, was about to be married before 275 family and friends – a guest list which included Marla Maples, the former model who the previous month had finalised her divorce from New York property tycoon Donald Trump.
For sheer star power, however, no one could compete with the family A-listers: John F. Kennedy Jr, the 38-year-old son of the slain president, and his elegant wife, Carolyn Bessette- Kennedy, 33. JFK and CBK were New York’s ‘It couple’, the closest America came to homegrown royalty.

Another Kennedy tragedy
However something was wrong. Dusk had faded into night, and the couple had not yet arrived. The small, single-engine plane that ‘John John’ had piloted for the short journey from New Jersey to Hyannis had apparently disappeared off the coast of Martha’s Vineyard. Kennedy, who had only obtained his pilot’s license the previous year, had not filed a flight plan nor kept in contact with air traffic control, complicating the search for survivors.
At dawn that Saturday morning, the Coast Guard believed there was still hope of finding the Kennedys alive. The world was gripped by the ongoing search – but five days later, the bodies of Carolyn and her sister, Lauren, were discovered close to the plane’s fuselage. John Jr was found trapped under his seat. On the orders of President Bill Clinton, the White House flag was lowered to half-mast.
Senator Ted Kennedy, the patriarch of the family, said of his dead nephew: “Like his father, he had every gift but length of years.” America mourned the loss of yet another Kennedy and also his luminous wife.

An American fairytale
The events of that July night, and the turbulent seven-year relationship that led up to it, have now been dramatised in Love Story, a mini-series streaming on Disney+. It’s from the American Crime Story franchise, which brought to the screen versions of the O.J. Simpson trial, the murder of fashion designer Gianni Versace, and Bill Clinton’s affair with White House intern Monica Lewinsky.
JFK Jr lookalike Paul Anthony Kelly plays the lead role; Sarah Pidgeon, from The Wilds and Tiny Beautiful Things, stars as Carolyn and delivers a mesmerising performance in which she captures the self-assurance of the sassy bride. Australian actress Naomi Watts has been cast as JFK Jr’s mother, Jacqueline Kennedy Onassis, while Grace Gummer, the daughter of Meryl Streep, plays JFK Jr’s sister, Caroline.
Played out over nine episodes, the series is a turn-of-the-millennium fairytale. There’s even a Cinderella feel to the couple’s first encounters, which came after Carolyn gatecrashed a Manhattan soiree. It’s not so much Disney+ as Disney Gen X – Cinderella meets Sex And The City. One expects Carolyn to have lunch with Charlotte, Miranda, Samantha and Carrie. In the ’90s, after all, JFK Jr. was ‘Mr Big’.

A Kennedy prince
JFK Jr had been a central figure in America’s great postwar melodrama since his third birthday on November 25, 1963. It was then – at his mother’s prompting – that he movingly saluted his father’s coffin during the funeral in Washington, D.C. After Jackie said she wanted her husband’s presidency to be remembered as an American “Camelot”, John John and his older sister, Caroline, came to be regarded as a prince and princess. And as soon as he was old enough to date, the handsome scion of the Kennedy dynasty became America’s most eligible bachelor.
Romances with Madonna and actress Daryl Hannah only heightened his celebrity. With many speaking of him as a future president, JFK Jr fused the worlds of politics and glamour when he launched the glossy magazine George in 1995. On the first cover of his Vanity Fair-style monthly, supermodel Cindy Crawford was dressed up as America’s first president, George Washington.
For all John John’s celebrity and blue-blood connections, it was a little-known New York publicist, then working for fashion designer Calvin Klein, who captivated him.
The American ‘it girl’
For much of her childhood, Carolyn Bessette was raised by a single mother who worked as a substitute teacher in Yonkers, an unfashionable New York suburb. So, from their first chance meeting in the early 1990s, this was very much a picture-perfect tale of romance, casting “Carolyn as the commoner who had found true love with Prince Charming,” according to author Edward Klein.
JFK Jr was still dating Daryl Hannah when he and Carolyn started seeing each other.
“She’s stunning,” he told friends. “Enchanting.” But when Carolyn saw a picture of him in the papers holding hands with Daryl at a movie premiere, she ended their fledgling romance. He sent flowers and left messages, but to no avail.
“She was the ultimate cool girl,” her friend Carole Radziwiłł – who was married to JFK Jr’s cousin, Anthony Radziwiłł – told the Juicy Scoop with Heather McDonald podcast last February. “Even with John Kennedy, she did not care.” It was only after Jackie’s death in 1994 that Carolyn made contact again. One of her great regrets was that she never met John’s beloved mother.
True love
Friends spoke of JFK Jr’s obsession with his girlfriend, a passion made stronger by her occasional aloofness. In July 1995, while on a fishing trip off the island of Martha’s Vineyard, he proposed. It reportedly took Carolyn three weeks to say yes.
Rather than hold a grand society wedding, the couple tied the knot on September 21, 1996, in a wood-frame church on Cumberland Island, Georgia. The ceremony was attended by just 40 friends and family. The timing and whereabouts were closely guarded. The bride, sealing her reputation as a fashion icon, wore a US$40,000 pearl-coloured slip dress created by a close friend, the then-little-known fashion designer Narciso Rodriguez.
The nuptials were dubbed “the wedding of the ’90s”, with Carolyn’s simple gown having a transformative effect on bridal wear around the world. Ralph Lauren reportedly told his designers to “think
of Carolyn Bessette” whenever they created a new look. Her chic elegance made her a “modern-day Jackie O” – which friends of JFK Jr thought might have explained his attraction.

Trouble in paradise
So much for the fairytale. Like the union between Prince Charles and Princess Diana, the great romance of the 1980s, the relationship began to fray. Books on the couple have detailed Carolyn’s discomfort at being fodder for the New York tabloids, as well as the time she spent with friends from the fashion world, where cocaine use was rife. Then there was her ongoing friendship with a former boyfriend, Michael Bergin, who had modelled for Calvin Klein. Noah Fearnley has been cast to play Bergin in the series.
John Jr complained his wife was too controlling, and physically and psychologically abusive. These claims are hard to verify, but have been woven into the narrative of their marriage. In the spring of 1999, the pair were reportedly in counselling. By the summer they were living apart. Carolyn remained in their Tribeca apartment, while John Jr moved into a hotel suite overlooking Central Park. For screenwriters looking to make an explosive mini-series, their troubled marriage offered an orchard full of low-hanging fruit.
Throughout, the series shows how fortune can turn quickly to misfortune, culminating in the crash which took the couple’s lives.
The Kennedy curse
John Jr had suffered a broken ankle earlier in the year and been instructed by his medical team not to fly while on crutches. The pair took off later than planned that July evening, making the flying conditions more hazardous. Supposedly this was because Carolyn had agonised over the colour of her nails at a Manhattan pedicurist. It is the opening scene in the drama.
The dead prince. The strong-willed princess. It sounds like a tragedy of Shakespearean proportions, but it is also classically Kennedyesque. For all their celebrity and political power, the family has been beset by so much misfortune that the term “the Kennedy curse” has entered into popular usage. When the first reports came though that JFK Jr’s plane had gone missing, it was shocking, but not surprising.
“We were witnesses again to one of the singular facts about this singular family,” noted an editorial in The New York Times. “That it is a family of unfinished journeys, of magnetic personalities cut down far too early.”

Forever iconic
To this day, more than a quarter of a century after her death, Carolyn remains a ‘ghost influencer’, a fashion icon in perpetuity whose style enjoys an afterlife on TikTok and Instagram. Her legion of fans reacted angrily when photos were released showing filming of the mini-series on the streets of Tribeca, with Sarah Pidgeon dressed in a black leather blazer, brown silk skirt and black converse shoes. The wardrobe department, complained fashionistas on social media, had done CBK a terrible injustice.
As for John Jr, who knows what might have been? Though many felt he lacked the seriousness to mount a successful presidential bid, his star power and ancestral bloodline would have made him a formidable Democratic Party figure. Certainly, he had the celebrity to counter Donald Trump. And he would have been in his his mid-50s (his political prime) when the New York tycoon first won the presidency in 2016.
Bizarrely, he is now caught up in the conspiracy mill of modern-day US politics. Fantasists in the QAnon movement believe he is still alive. In November 2021, on the 58th anniversary of the assassination of JFK, many of them gathered in Dallas’s Dealey Plaza to await John John’s emergence from hiding. Some members of the crowd even wore T-shirts reading ‘Trump-Kennedy 2024’. They expected him to declare support for the then-former president, and agree to become his running mate on the new campaign.
Love Story, then, has it all – politics, glamour, fame, fashion, ambition, pathos. This was a story where reality was just as dramatic as fiction.
Love Story is available to stream now on Disney+.