Americans old enough to remember exactly where they were and what they were doing when his father died thought John F. Kennedy Jr bore the weight of the Twentieth Century on his shoulders. But to the young women born after November 22nd 1963, young John wasn’t just famous. He was a catch.

The mania was inescapable. In 1988, after 

 magazine announced that he was the sexiest man alive, the 28-year-old became so besieged by girls that he had to develop a survival strategy. He tried to give off the impression that he was never single — an ingenious ruse which required dating as many women as he could. Madonna, Cindy Crawford, Brooke Shields, Daryl Hannah, and Julia Roberts were each deployed as human shields. It didn’t work. By 1989, JFK Jr needed some time away from the squealing stalkers of Manhattan. So he booked a holiday with some friends to go mountain climbing in Washington state, south of Seattle, just to get away from it all. No strangers asking for his number, no weirdos demanding dates — just him and his buddies and the wilds of the Cascade mountain range. Bliss.

But things didn’t go to plan. It soon transpired that, halfway up Mount Rainier — one of the biggest active volcanoes in the world — a high school girl was lying in wait for John. “I knew you were coming here, so I came up because my prom is tonight,” she said, hoping to snag a dance with America’s most eligible bachelor. Later, on the flight home to New York, another woman sat in the empty seat next to John. She introduced herself as an off-duty flight attendant who found out his schedule and flew six hours out from New York to Seattle that same day so she would have the chance to meet him on the six-hour trip back east. Twelve hours on a plane in one day, all to see John. “You gotta rescue me,” John begged his friends, who just laughed. Like a scene from a French farce, there was a third woman waiting for John at the airport in New York, naked under a huge mink coat. It was one of his new girlfriends — an actress by the name of Sarah Jessica Parker. Some vacation.

It’s no mean feat to live a well-adjusted life with a surname as heavy as Kennedy (not to mention a jawline like a post-juice cleanse Adonis.) But John F Kennedy Jr bore the weight more profoundly than most. Known affectionately by the American public as ‘John John’, John Kennedy Jr had his childhood etched into the national memory via two images. The first was a picture of him as a baby, happily bootling about by his father’s feet on the carpet of the Oval Office. The second was taken on the occasion of his third birthday, three days after JFK was assassinated — a desperately sad vignette of a child saluting his father’s coffin with a tiny hand. As an adult, John said he couldn’t remember that day – in fact, he said he had no memories of his father whatsoever. Whether that was true or not, the answer nimbly deflected the questions he was forever being asked — and helped him to prise himself out of that grainy footage from 1963, and out from underneath his father’s name.

Counterfactual historians like to imagine what would have happened to America had JFK never been murdered. Would it still be the shining city on the hill, twinkling even brighter? Or would the country have continued tumbling down to its status today as the dirty village in a hole? More intriguingly, perhaps, the same question is now sometimes asked about JFK’s son, John. On the night of July 16th 1999, he crashed his plane in the sea off Martha’s Vineyard and died, aged 38. His wife Carolyn Bessett and her sister Lauren were also on board, perishing alongside him.

John F Kennedy works in the Oval Office, while John John plays


That crash, a cruel modern evocation of the bloated Kennedy Curse, left forever unanswerable questions about John’s political future. But it also preserved in amber his and Carolyn’s status as America’s most gorgeous and promising couple — a pair often dubbed the “torchbearers of a new generation”. With their elegant style, their fabulous celebrity friends, their lives of wonderful luxury, their enviable cheekbones, and their pole position in the bluest of blue-blood families, images of them now evoke a halcyon, bygone era. There was a time, before 9/11, when being young and sexy in Manhattan with a big loft and a little phone and a pack of Marlboro Light 100s was the pinnacle of Earthly cool. John Kennedy and Carolyn Bessett were the icons of this world: The New Camelot, as some observers called it, referring to JFK’s inner circle of 30 years before.

"Half way up Mt. Rainier, a high school girl was waiting for John..."

It is not without its courtiers, even now. John and Carolyn still inspire countless fashion Instagram accounts, all with tens of thousands of followers, that scour photo archives for snaps of him rollerblading in Central Park, or her strolling through Manhattan in a leather jacket and rectangular sunglasses looking like an advert for Calvin Klein, where she worked as a stylist. One Carolyn super fan has amassed a sizable online following by identifying and tracking down her old outfits, and recreating her minimalist looks with archaeological precision. And this fanatic army of New Camelot only looks set to grow. Ryan Murphy, the 

 creator, announced this year a new TV project called 

, which will retell the poignant saga of John and Carolyn’s romance. Turtle necks and bootcut jeans are going to be huge in 2022.

JFK Jr. on his first day as Assistant District Attorney


Ronald Reagan once said that President Kennedy was a man who “seemed to grasp from the beginning that life is one fast-moving train, and you have to jump on board and hold on to your hat and relish the sweep of the wind as it rushes by.” He might just have easily said the same about John Jr — a constant fixture in tabloids and gossip magazines, first at Brown University, and then in New York. His speech at the Democratic National Convention in 1988 brought the house down. He was forever being snapped cheering at basketball games, cycling around the city, and playing frisbee in Central Park. He was extremely active – an avid kayaker, swimmer, surfer, weightlifter, parachutist, who took flying lessons and his own plane in order to zip along the East Coast.

The press loved to cover his less wholesome exploits, too. Like the time he amassed $2,000 worth of parking tickets, or left a post-college flat in such a dreadful condition that he was sued by the landlord — or the time when he failed the bar exam. (“The Hunk Flunks,” read the splash of one newspaper.) Steven Gillon’s excellent biography, 

 quotes an anonymous friend who says that John claimed to hate the attention — but that if he went too long without an appearance on 

, “he would do something like take his shirt off or rent a convertible”.

John was such a famous New Yorker that he featured as an off-screen character in an episode of 

, in which Elaine joins an aerobics class so she can admire “John John’s butt”. John didn’t see the episode, but in 1998 he described to Jay Leno the experience of walking into work the morning after it aired. “I come out of my house in the morning and everyone is yelling across the street,” he said. “People are driving by in their cars and honking and I’m going, ‘what the hell is going on here?’… I had a trial and I walk into the court and the defendant is sitting there and he goes ‘you were on 

!’ Then he leans over to his lawyer and he goes: ‘Guy’s an actor, too. No wonder he failed the bar exam!’”

Law was not John’s calling, and by all accounts he was too nice to send villains away. “He wasn’t a great district attorney,” Laurence Leamer, a Kennedy family biographer, said. “A lot of the bad guys were so delighted to meet John that they confessed.” Instead, John’s friends recall him toying with an entry into politics, the family business. (From 1947 to 2011, there has been one Kennedy or another in power in Congress, the Sentare or the White House.) But what he really wanted to do was launch a magazine.

“You can successfully launch a magazine in just about anything except for religion and politics..."

In1993, John and his friend, a PR executive called Michael Berman, began to form an idea for a new publishing concept. They wanted to launch a political magazine that didn’t appeal just to the gremlins of Washington D.C., but also to the ordinary human beings who had started to take an interest in the exciting political scene of the early nineties. So the pair signed up to a two-day seminar in called “Starting Your Own Magazine,” held at the New York Hilton. Early on, the lecturer told those gathered that “You can successfully launch a magazine in just about anything except for religion and politics.” But John believed he had spotted a gap in the market — and that nobody had yet exploited the emerging trend that saw politics colliding with celebrity. If the magazine’s essence could be summed up in one image, it would be Bill Clinton, wearing aviator shades, playing the saxophone on the Arsenio Hall Show. John and his team believed their publication should appeal to people who had never bought a political magazine before. It should also be gender neutral — a risky manoeuvre back then, when magazine advertisers either sold shampoo to women in 

“Politics isn’t dry. It isn’t dull. So why should a magazine covering it be?” John said in 1995 at the launch of 

, whose first issue featured Cindy Crawford on the front dressed as America’s first president — the eponymous Mr Washington of the title. It was a hit, selling out at half a million copies, and containing over 500 advertising pages — more than the September issue of 

 at the time. Like all the best publications, 

‘s competitors jealously sniffed that it was doing everything wrong, with one commentator dismissing it as a “net loss of information”. Treating politics as popular culture was genuinely ahead of its time — just think of today’s culture wars, where the two are not so much intertwined as entirely indistinguishable. And the truth is that every newspaper and magazine – especially those that accused 

 of dumbing down at the time– now treats politics like it’s downstream from culture. How much more do you know about Joe Biden’s life than his policies? A quarter-century on, and old copies of 

Around this time, John met Carolyn. Gillon’s book quotes a friend who worked with her when they were shop assistants in Boston, and she claims that Carolyn had a plan to move to New York to seduce John. She was voted “Ultimate Beautiful Person” by her classmates in high school, and after arriving in New York — and waving through various secondary-cast boyfriends — she met her prince. “John was a charmer,” recalled Marta Sgubin, the Kennedy family governess. “He’d charm a snake.”

They got married in secret, on Cumberland Island in Georgia, in an event of such great privacy that it would take more than 20 years for camcorder footage of the weekend to finally emerge. To keep the marriage out of the papers, John put the word out that he was going to Ireland for the weekend and printed the wedding programs in the 

 offices after the staff had gone home. (To excuse the subterfuge, he left cigars and Champagne for his employees). “Carolyn has changed my life in a way I never thought possible,” John said in a pre-wedding speech, surrounded by glowing friends.

But how hard it must have been for her, going from obscurity to one of the most-watched women in the country. John, on the other hand, grew up with onlookers hounding his every step. When his mother Jacqueline took John and his sister Caroline to live in Georgetown — their first home after the White House — tour buses would park outside so sightseers could gawp at the bereaved family. Now John and Carolyn were married, the paps set up permanent residency outside their Tribeca loft, waiting to give the insatiable fans another glimpse into their lives. The couple were a mobile landmark of Manhattan, a tourist destination that hopped around fancy bars and chic restaurants followed by admirers and photographers.

Today, you can find pictures of John and Carolyn carrying newspapers on their way to brunch, going to work, going shopping – and even a detailed montage of them fighting and crying and yelling at each other in Central Park. Carolyn has been accused by friends of being controlling, and John insensitive. She was rumoured to be on drugs – although someone from her inner circle said her cocaine use was no worse than anyone else’s in fashion circles at that time. Robert Littell, John’s old college flatmate, claimed she was unable to deal with the media pressure. He adds that rumours of John’s affairs have been overstated, saying perhaps a little too enthusiastically that he was a “monogamous guy who stuck to his knitting”.

John H. Davis, a Kennedy family biographer related to Jackie, once said there was “some kind of curse” hanging over the family. Five years after JFK was murdered, his brother Bobby was assassinated. The Chappaquiddick Incident cast a shadow over the youngest brother Ted’s career after a young woman died in his car in 1969. In the decades since then, the Kennedy name has been tarnished by family members who have made careers as anti-vaccine campaigners, drunken belligerents, and political also-rans.

The curse — if there is one — struck John on a summer night in 1999, when his Piper Saratoga aircraft crashed into the Atlantic. He had been flying to Martha’s Vineyard, carrying Carolyn and her sister Lauren to a family wedding on the island. It could be the hindsight talking, but pundits have described how John set off for the wedding at a crucial moment in his life.

"John was a charmer," recalled the family governess. "He'd charm a snake..."

Although they called each other soulmates, John’s marriage to Carolyn was going through a rocky patch, and for the past few days, he had been staying at the Stanhope Hotel. Thanks to Lauren, the night before the crash, the two had reconciled. 

 was also in a difficult position. Michael Berman, John’s business partner, had left amid acrimony, and there were black clouds looming over the company’s balance sheet. Stressed, tired, his fractured ankle still in pain after a hang-gliding accident, John took off from Essex County Airport in New Jersey into hazy conditions as dusk was falling. His plane was swallowed by the night.

The disappearance of John Kennedy was deemed to be such a national emergency that President Clinton deployed the Navy to help search the coastline along his flight path. The Coast Guard found the bodies on the sixth day. They died on impact. A thousand conspiracy theories have emerged in the years since to explain what happened. (One school of thought that is unencumbered by reality suggests that Hillary Clinton herself may have sabotaged the aircraft to remove John from the list of possible New York senate contenders for the 2000 election.) The truth is much more mundane. The prevailing explanation says that John probably became spatially disoriented, which can occur when a pilot’s inner ear tells them their aircraft is level when it isn’t. Flight instructors say that when it’s dark the trick is to trust the instruments that show the plane’s actual position in the sky — a technical skill that Kennedy had not yet mastered.

President Bill Clinton breaks the news of the disappearance of the Kennedy&#8217;s plane, 1999


“The strangest, most inexplicable thing that happened that last day is that John didn’t take a copilot with him,” Leamer, one of the Kennedy biographers, has said. A copilot had offered to ride with John on the day of the flight, but was turned down. “John was such a careful pilot that of the 200-or-so hours he had flown, he had an inordinate number with a copilot. He knew he wasn’t a great pilot. Why John didn’t take the pilot with him is just one of those things we’re never going to know.”

 thinking, and many of John’s friends believe that the night he died shut off a glittering career in politics and the fulfilment of the New Camelot promise. Those who knew John in the eighties and nineties have said that 

 was a way for him to test the waters before going into politics. Brian Steele, who worked with John during his stint in law, believed John would have run for Governor of New York in 2002, sought re-election in 2006, then entered the presidential race in 2008. “His legacy is all about who he would have become,” Steele once said. “America, and maybe the world, would have been a better place.” Elsewhere, the media began Diana-grade weeping. One TV pundit mourned the loss of the “moral leader for the next generation of young Americans”, which John would probably have been the first to deny.

"We dared to think that this John Kennedy would live to comb gray hair..."

That sort of pondering and soul searching doesn’t just engage the commentariat whenever a new biography comes out. QAnon, the bonkers conspiracy theory factory that believes a Satan-worshipping gang of cannibalistic paedophiles secretly pulls all the strings in government, also gets involved. One conspiracy claims that John faked his own death off Martha’s Vineyard, and has been living under the identity of Vincent Fusca, a sales manager from Pittsburgh who looks absolutely nothing like him. It prophesied that John would reemerge just in time for the 2020 election, when a man whose surname was synonymous with the Democratic Party would serve as Donald Trump’s Republican running mate and save the world. “Cannot wait for the great reveal,” reads a typical comment underneath a YouTube video about John. “Come on out John John!”

It says a lot about these conspiracists that John’s failure to reappear last year has not dampened their belief that he one day will. Unlike his friends and family, at least the QAnon loons don’t have to cope with his loss. For them, he’s still around. At the funeral, Uncle Ted eulogised this extraordinary man who had grown up to symbolise so much for a generation of Americans. “We dared to think,” he said, “that this John Kennedy would live to comb gray hair, with his beloved Carolyn by his side. But, like his father, he had every gift but length of years.”

This article originally appeared in the Winter 2021 issue of Gentleman’s Journal. Join the club 

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