In​ 1978, Jacqueline Onassis thought it a good idea for her teenage son John to spend some months away from New York with the Youth Conservation Corps of the Yellowstone National Park. But John didn’t fit in, so she rang John Perry Barlow, a lyricist for the Grateful Dead and owner of a twenty-thousand-acre Wyoming ranch. Barlow had been in San Francisco for the Summer of Love; he knew Andy Warhol and everyone at the Factory. Acid was his thing: he denounced cocaine as a Republican drug because it made its users selfish. John Kennedy went to Wyoming.

‘My first impression of him,’ Barlow wrote in his memoir, Mother American Night, ‘was that he was incredibly good-looking and had a kind of thoughtless grace.’ He was ‘physically powerful and fearless’. On drives into the West they took acid. Then there was the work of the ranch: bailing hay, corralling cattle, dropping explosives into mile-deep gas wells and flying Barlow’s plane. Barlow recognised the way John affected people. A college friend of John’s said: ‘I have never seen anyone get reactions the way he did – not the biggest rock star, not the biggest movie star.’ Barlow said of those who flocked to glimpse him: ‘You could see them just shedding IQ points as they approached. I mean the closer they got the dumber they were … By the time they got there they were as dumb as bait.’

I went to work at John’s magazine, George, in the summer of 1996. He could bring on what I’ll call ‘speech regret’ – when you say something for no reason, which you don’t really mean and which has no point. Early on I was walking up Eighth Avenue with John and other colleagues. We were going out to lunch. The offices of the magazine were on Broadway and West 50th Street and I said something inane about how the shops round there seemed to change all the time. ‘You sound just like a tourist,’ John said – I thought I sounded stupid.

In Love Story, this year’s Disney+ series about John and Carolyn Bessette, the George offices are in a building so close to the neighbouring skyscrapers that people can look right into John’s office. As it was, the views from the 41st floor were epic and uninterrupted. From my south-facing window, the panorama was of Midtown and the Hudson, the World Trade Center, the harbour beyond and then the American continent. During Fleet Week, at the end of May, a US aircraft carrier group would dock at the Midtown piers – the carrier seemed to dwarf the Twin Towers. Looking down at the streets below, you could see lines of sailors in white uniforms looking like trains of ants weaving their way into the city. My desk was in a booth by a low wall that separated me from John’s secretary, the formidable RoseMarie Terenzio. John depended on no one more than RoseMarie. ‘Here’s the deal,’ I’d hear her say, before the door to John’s office slammed shut.

San Diego or Chicago? That was the question presented to the editors by John soon after I joined. The Republican convention would be in California, the Democratic convention on Lake Michigan. I chose San Diego. It was already near certain that Bob Dole, the Republican candidate, would lose the 1996 presidential election. Bill Clinton had ground down the campaign waged against him by the speaker of the House, Newt Gingrich. So what would happen at the Republican convention? Might a non-event be interesting, anthropologically if not politically?

San Diego has several famous old hotels, none more so than the Hotel del Coronado, where Billy Wilder filmed Some Like It Hot. The accommodation we had been assigned by the Republican Party organisers was the Days Inn and Suites, on Rosecrans Avenue, a good distance from the convention. Others staying there included Sidney Blumenthal, then at the New Yorker, and two journalists from the Daily Telegraph – William Deedes, on whom Evelyn Waugh modelled William Boot in Scoop, and Ambrose Evans-Pritchard, who would make a career attacking the Clintons. Deedes and Evans-Pritchard’s way of covering the still-born convention was to hit the golf course. And it really did seem as if nothing much was going on. In the lobby of one hotel, a TV station was broadcasting reruns of Ronald Reagan’s acceptance speech from 1984. ‘I’m a Dole Man’ was played over loudspeakers as the candidate arrived by paddle steamer, a rendition of the Sam and Dave song ‘Soul Man’, only Dole Man sounded more like Dull Man.

Elizabeth Mitchell, known as Biz, John’s number two at George, suggested one evening that we drive half an hour north to Escondido, where Pat Buchanan, who had lost the nomination to Dole, was holding his convention-in-defeat. His guests included Oliver North, the disgraced Marine colonel from the Iran-Contra scandal of the 1980s, and Phyllis Schlafly, the author of A Choice Not an Echo, written in support of the 1964 Barry Goldwater campaign. Anti-feminism, anti-equal rights – Schlafly was both and a lot more. Her funeral in 2016 was attended by Donald Trump. During his campaign, Buchanan said: ‘What we have is a lawless situation on the southern border of the United States where this country is literally being overrun by people who are violating our immigration laws and defying the American Constitution.’ He proposed building a wall between the US and Mexico. Buchanan was anti-Nato, anti-UN. ‘We’ve got to get back to the idea that we Americans govern ourselves,’ he said. ‘We’re not governed by judges, or little dictators in black robes.’ In 1996 this didn’t seem likely ever to become governing rhetoric.

At the office one morning at the end of August, I was approached by Richard Johnson, the editor of the New York Post’s gossip column, Page Six. Every day, a photocopied packet of the gossip columns from the national and local papers was prepared by the interns at George. This was one way to keep up with public versions of John. By the elevator doors, Johnson asked me why John and Carolyn hadn’t been seen together for some time, and were the rumours accurate – had they broken up? I told him I had no idea – which was true. As we later learned, the false impression they had separated was part of their plan to preserve the secrecy of their wedding. A fortnight later, John and Carolyn married in Georgia.

Shortly afterwards, New York Magazine ran a profile of Carolyn and John by Rebecca Mead. It was called ‘Instant Princess’:

Among the disparate pieces of information about the John F. Kennedy Jr-Carolyn Bessette marriage released by Senator Edward Kennedy’s office last week, there were delicious details of tailoring (the bride’s veil was silk tulle ‘with a hand-rolled edge’), ornithology (Cumberland Island, where the wedding took place, is home to ‘over three hundred species of birds’) and nomenclature (‘Gogo’ Ferguson, the family friend! Narsico, the exquisitely named dress designer!) … But none of the snippets meted out about Bessette Kennedy … appeared to provide the key to understanding exactly why she, of all women, should have been the one to relieve John Kennedy of his bachelor status.

‘Do you know Rebecca Mead?’ John asked me. ‘Take her out to lunch. See if she’d write for George.’ I asked what had impressed him about the piece. He said Mead had asked a lot of deliberately wrong questions that provoked people into giving her right answers. John had spent years reading about himself in the tabloids – part of an effort to control and preserve his public and private selves. Mead seemed closer to the mark.

The White House​ Correspondents’ Dinner is held every spring in the subterranean ballroom of the Washington Hilton. The blue lights make you think for a moment you are several fathoms under an ocean. In 1997 there were 260 tables, each set for ten people, and a dais where the presidential party would sit. Ten thousand plates were sent out from the kitchens over the course of the evening. Some of us set out for the Hilton early for the pre-dinner action. Many small rooms, many people, only there was no traction, or none that I could find, and no place to settle. I headed to the ballroom to check the menu – steak and salmon – and to look through the pamphlet that listed all the guests, a Who’s Who of American political journalism.

‘Hello Inigo.’ I turned. It was Carolyn. I got up, but we were at once surrounded by a wall of photographers. It’s easy to look stunned when paparazzi swarm en masse: you are stunned, you are blinded. Ushers arrived to sweep the photographers away. John and the rest of George took our places. The evening proceeded, the steak and salmon came and went, though you’d be hard-pressed to distinguish the two. A comedian (Jon Stewart) made polite jokes about Bill Clinton; Clinton made his jokes in return. That night he made fun of the journalists covering the investigation of the Whitewater property scandal. ‘I know you give me grief from time to time,’ he said, ‘but really we work around the clock trying to help you do your job.’ As it later turned out, he had recently ended his affair with Monica Lewinsky.

On the way out, John and Carolyn became the object of extraordinary attention, as journalists and editors closed in. I thought of how being touched by a monarch was once believed to be a cure for scrofula. The last place I expected to see a feral version of the royal touch was in the ballroom of the Hilton in Washington. But that’s what it looked like, as if there were a form of magical absolution involved in approaching this couple.

Whether starting a glossy magazine was a good idea for John or not, you could see why running his own publication suited him. He was going to be in the public eye, so why not do it on his own terms? And it allowed him to be connected to a political world he felt ambivalent about joining. Unlike a TV show, a monthly publication didn’t require him to speak in public unless he chose to. Magazines were glamorous and they gave you something to hide behind. One of the George features was John’s monthly interview. Early on, an executive at Hachette, which backed George, proposed that John interview Marina, the wife of Lee Harvey Oswald, without thinking what, exactly, they would have to say to one another. David Pecker, the CEO, who later ran the National Enquirer, complained that John didn’t interview popular people such as Princess Diana or the imprisoned Mafia boss John Gotti. But he did interview the Vietnamese general Võ Nguyên Giáp. He spoke to Marion Hammer, head of the National Rifle Association, as well as Louis Farrakhan, George Wallace, Gerry Adams and others. After the interview with Adams, John was disinvited from a party for Tony Blair.

One person John very much wanted to interview was Fidel Castro. There was hope that it might happen in the early autumn of 1997, and John asked me to prepare for the journey and the conversation. It was the 35th anniversary of the Cuban Missile Crisis, and a new book was about to be published: the transcripts of the executive committee John’s father had formed to manage the crisis on 16 October 1962, two days after an American spy plane flew over western Cuba and took photographs of ballistic missile sites under construction.

In early October the word came through that this might be a good time to make the trip. John asked the fashion photographer Herb Ritts to take portraits of Castro if we got to meet him. Also travelling with us was Herb’s assistant, David. Being late and forgetful were characteristics that Barlow had recognised in John twenty years earlier: both were evident the morning we set off from JFK. John hadn’t showed up when we boarded the plane. Herb and I wondered: do we go? The door was about to close when John burst in and collapsed into the front row. Then, on the way to Mexico, he said he didn’t have his passport. Thoughtless grace could occasionally be thoughtlessness. Reverse-charge phone calls were made in Cancún to RoseMarie in New York, who then rang the Cuban foreign ministry in Havana. John’s passport would be sent to Havana in the Cuban diplomatic bag.

The descent to Havana’s José Martí Airport was steep and swift, the tilled soil seen from the windows of the plane was red. In the arrivals hall, cocker spaniels swarmed over the luggage hunting for explosives. An official led us through immigration. We were introduced to the three people with whom we’d spend the next four days: a driver, a guide and a government official who looked as if he doubled up as bodyguard. They took us to the Meliá Cohiba Hotel on the Malecón, the Havana waterfront where Cubans gather in the evenings to look out at the sea that divides them from the US.

There was a semi-official factor to the visit even if at the outset there was no indication of whether we’d meet Castro. On the first evening we were taken to meet Ricardo Alarcón, the head of the National Assembly, at his home not far from the hotel. The next morning we were shown around the Museo de la Revolución, which houses the engine of the U-2 spy plane shot down during the missile crisis, then José Ramón Fernández, the commander who had led the campaign to defeat the CIA-backed guerrillas at the Bay of Pigs in April 1961, brought out the maps he had used to repel the invasion.

The history of Cuba on this tour was the history of its revolution and how it saw off the United States. It was inevitable we’d be taken to the Bay of Pigs, where we were encouraged to swim, an invitation that was turned down. I couldn’t tell whether the invitation was a trap – to see John in the water at the site of a Kennedy humiliation. But I wondered how anyone in the CIA could have believed that landing troops on a beach with just three causeways leading inland, through vast and thick mangrove swamps, was a good idea.

Our minivan drove onwards to a resort at Caleta Buena, the Good Cove, an inlet surrounded by coral. Russian tourists drank rum and dive-bombed one another in the water. They had no interest in us, but nor did anyone outside the Meliá Cohiba. Beyond Havana, John was just another gringo on holiday. The photographs I have of the Cuban adventure seem entirely mundane, as holiday snaps often do. Herb taking pictures of Cuban buildings, the four of us sitting in a café or posing in front of a Hawker Sea Fury propeller fighter that Britain exported to Cuba in the 1950s and which was used to strafe the would-be invaders in 1961. John didn’t say anything about his anonymity on the island, yet it was obvious he appreciated it.

A message was relayed by the official travelling with us: we should get back to Havana. The minivan was now like a holiday camper, with papers and crumbs everywhere. The journey meant driving on Cuba’s one motorway, which every now and then was cut through by a railway line. On the outskirts of Havana, young Cubans in old American cars played their version of chicken – we sailed past them, some indication of how slow and worn out the cars were. At the Meliá Cohiba, there were fresh instructions: be ready to go to dinner. The invitation did not extend to Herb.

At 8.30 we were met by the official and the guide and driven to a brutalist building with an imposing staircase. At the top were some of the people we’d already met: Ricardo Alarcón; José Ramón Fernández; Juanita Vera, Castro’s translator; his 32-year-old chief of staff and future foreign secretary, Felipe Pérez Roque; and several others. This was the brief animated phase of the evening before everyone fell silent. We were led down a corridor filled with tropical plants. Castro was waiting behind some foliage, dressed in his battle fatigues. Hands were shaken, and John gave Castro a proof of the forthcoming book. Castro asked whether John was the same size as his father. ‘A little taller,’ John replied. ‘A little thinner.’ He was about to turn three when his father was killed. Castro passed the book on, and said he had been reading Winston Churchill and Stefan Zweig, both of whom visited Cuba; Churchill was a journalist and military observer following the war of independence in 1895, three years before the decisive US intervention. None of the Cubans apart from Castro and his translator said a word. ‘What did you think of Nixon?’ John was asked.

What followed was a five-hour, five-course dinner at a broad table covered with an embroidered cloth: grapefruit sorbet, consommé, shrimp, chicken and ice cream. John sat opposite Castro; I was on the president’s right. The name card in front of me omitted my surname: was I meant to think that while I was welcome, the family surname was not? My father’s book on Cuba remains banned. Some people’s speech is easy to remember: Castro’s was not. He would make a point then venture out on a parabola, adding detail, stories and observations about people who interested him – that the pope got up so early in the morning – before eventually returning to the point he’d made, such as no, the Baptist Church did not play a crucial role in the Cuban countryside before the revolution.

Only at the end of the evening did Castro return to the subject of John’s father. As we were leaving the dining room, he stopped and said: ‘You know Lee Harvey Oswald was trying to get to Cuba.’ Oswald had been refused a visa at the Cuban embassy in Mexico City a few weeks before the assassination. John nodded, and Castro walked on before stopping again. ‘You know it was hard to allow Americans into Cuba at that time,’ he said. John nodded again. We said our goodbyes, walked down the steps to the waiting minivan, watched by everyone above, and drove back to the hotel. Herb came down for several 2 a.m. whiskies.

At breakfast the next morning, John was furious. He felt cheated. He had travelled to Cuba, he had wanted a real interview and now he would be returning empty-handed. Phone calls were made to New York and to the foreign ministry: for a moment I wondered what would happen if this became a full-scale diplomatic row. Reassurances were offered: maybe next time. John’s temper dissipated. We’d each been given a box of cigars, which turned out to be Churchills, made by Churchill’s favourite cigar-maker, Romeo y Julieta. The boxes were wrapped in puce-pink paper. If the idea was to disguise the contents, that failed: it was entirely obvious what was inside. Since it was illegal to bring Cuban cigars to the US, it wouldn’t look good if John was stopped at customs. I said I’d hide them in my luggage.

On the plane from Cancún to New York, I thought about those two cryptic remarks Castro had made as we were leaving the dinner. They seemed vague yet deliberate. Like the missing surname, something was being said but in an unspoken way. Was this Castro’s way of saying he knew nothing about the assassination but that if he had allowed Americans into Cuba in 1963 then Oswald would never have been in Dallas? Observations like these were not up for discussion with John. He, too, had a way of saying things in his own unspoken way. Once we were out of the airport, I handed John his pink-wrapped box. At Newark Airport, John was swept through without a thought of where he might have been. He had no need of a passport. This was another dimension to his fame: he had liberties that were given to few others. Not many people had it in them to say no to John.

Accounts​ of John and George are now numerous. Richard Blow, one-time executive editor of the magazine, wrote about his experience in American Son (2002). He was one of the first senior editors when it was founded in 1995. The design director, Matt Berman, wrote about his life with John in the art room in 2014. RoseMarie Terenzio wrote a memoir, then edited an oral history. America’s Reluctant Prince, a biography of John by Steven Gillon, came out in 2019. Elizabeth Beller’s Once upon a Time, her life of Carolyn Bessette Kennedy, was published in 2024 – Love Story is based on it.

All these books illustrate the two central problems with George: structural and personal. Hachette didn’t have the pockets of Condé Nast, nor were they strongly invested in the writerly dimension of the magazine. Contributing writers at Vanity Fair could be paid more than $200,000 a year. Bryan Burrough, a former Vanity Fair contributor, says that in his best year he was paid $500,000 for three pieces. That sum must have been about twice the entire annual budget for feature writing at George.

The second problem was John’s ambivalence about attacking people, whether they were politicians or not, and about journalism in general. John admired Dennis Rivera, the New York union leader who championed healthcare reform. He invited Marc Morial, then the youngest ever mayor of New Orleans, to come and talk to the office. But covering the Clinton presidency was more complex – or more thwarted. As exercises in self-defeat go, could anything match Clinton’s affair with Lewinsky? Denying it, as Clinton did, even more so. Yet John was reluctant to pursue the story. You could, if you were John, choose to avoid it for personal reasons, but journalistically – that was a failure.

Working at George was never dull, despite the contradictions emanating from the editor-in-chief – and often because of them. For many of the staff, it became a life. Towards the end, though, the sense of impending trouble was strong and unmistakable. I never knew why Hachette decided to sever relations. Nor did I know, until I read Gillon’s biography, why John’s marriage with Carolyn became tumultuous. She had become a remote figure in the office. On 16 July 1999, there was a staff meeting. John said there would be changes: not everyone would make it to the magazine’s next phase. But nothing would happen right away. The meeting ended, it was a Friday and the office mostly emptied out. A little later, John came back in with his sister-in-law, Lauren Bessette. She wore a light, white summer dress; he was in shorts and a T-shirt. They wanted books for the weekend and because I was the books editor they stopped by my desk. Lauren took a proof copy of John McCain’s memoir, Faith of My Fathers; John plucked out Stephen Fry’s novel Moab Is My Washpot. The two were then off down a corridor to the elevators. I knew nothing about where they were going.

William Langewiesche​ was once a commercial pilot who eventually became a famous contributor to Vanity Fair. But one of his most renowned pieces was published in the Atlantic Monthly in the early 1990s. In it, he discussed the way planes bank and dive:

Unguided any airplane will eventually begin to bank … But as the bank tilts the lift force of the wings, reducing their vertical effectiveness, it erodes the equilibrium that previously countered the pull of the earth. The airplane responds to the loss by lowering its nose and accelerating. Sitting in the cockpit with folded arms and watching it proceed is like letting a temperamental horse gallop down a steepening slope: it requires steady nerves and a morbid curiosity. In flight the slope steepens because the acceleration tightens the airplane’s turn, which increases its banking angle, which causes further acceleration … The airplane banks to vertical or beyond, and points its nose straight down.

That’s the spiral dive. In its most lethal forms it is called the graveyard spiral. The airplane flies in ever steeper circles and either disintegrates from excessive speed or hits the ground in a screaming descent.

This is what is believed to have happened to John as he flew his Piper Saratoga to Martha’s Vineyard after leaving the George office that Friday evening, with Carolyn and Lauren Bessette. John became disorientated after descending from five thousand to three thousand feet, according to the National Transportation Safety Board report on the crash issued a year later. The report was unequivocal: pilot error ended the lives of everyone on board. There was no new grassy knoll, there were no hidden hands, no suggestion of a conspiracy leading to Havana or to New Orleans. There was also a broader context: this was just one of 1463 accidents involving single-engine propeller planes in 1999, 233 of them fatal. John was not the only pilot that summer who made an error of judgment.

I still have the cigar box I was given 29 years ago. Inside is the last of the 25 cigars along with the photographs I have of that journey to Cuba in October 1997. One of them is of John, Herb and me standing in front of the Hawker Sea Fury at the Bay of Pigs. They are both beaming; I look less certain. In another, at Caleta Buena, John and Herb are lying in the sun. John is in swimming trunks, Herb in a T-shirt, shorts and a baseball cap. John looks happy and – there’s no doubt about this – godlike. Herb, the world-famous photographer, looks absolutely thrilled to be in the picture.