25 years after her tragic death, Carolyn Bessette-Kennedy remains a beautiful enigma (2024)

There are just two known recordings of the voice of fashion icon Carolyn Bessette-Kennedy. One is eight seconds long. (“It was a very exciting and wonderful evening,” she tells a red carpet reporter at a ball in 1998.) The other is barely two. It is deep and elegant. Almost musical. A voice for gala receptions and charity dinners, for conversation about summer plans and trips to the Hamptons. It sounds like money. On the Instagram accounts dedicated to her memory, Bessette-Kennedy’s fans – often youngsters born long after she and her husband John F Kennedy Jr were killed in a plane crash in 1999 – pore over these clips. They pore over photos of her, too – the crisp lines of her wardrobe, the ice-blonde of her hair, that unmistakable aura of a woman both beautiful and doomed. She’s a mystery to solve. Answers are rarely forthcoming.

That hasn’t, in the 25 years since Bessette-Kennedy’s death, been much of a problem. One of the great enigmas of late 20th century American celebrity, she has been credited with popularising a quiet sort of luxury, long before “quiet luxury” became a trending term. Think minimalist separates, black sandals, oversized white shirts. Very chic. Very tailored. Very Calvin Klein, where she worked as a publicist before her marriage. She is one of the beacons of the “Flashback Friday” genre on social media – images pulled from the archives and representative of what feels like a distant and more innocent past. And if not more innocent, at least more fun. That she died so young and so tragically, at the age of just 33, only harnessed her mythological allure.

Two new books claim to fill in the gaps. JFK Jr, by his former executive assistant RoseMarie Terenzio and journalist Liz McNeil, is an oral history of the handsome crown prince of America’s most famous family, whose celebrity status and mogul ambitions looked set to make him as big as his parents, president John F Kennedy and Jacqueline Onassis. Ask Not: The Kennedys and the Women They Destroyed, by journalist Maureen Callahan, is as lurid as its title – a potted history of sexual nightmares at the Kennedy White House and beyond. Both are being billed as definitive retellings, and both devote significant time to Bessette-Kennedy, her glamour and her multitudes. However, where JFK Jr is ever slightly too clean, Ask Not is too salacious. Bessette-Kennedy becomes even more of an unknown as a result. She’s either an aloof martyr or a drug-addicted social climber. You leave none the wiser.

What JFK Jr does do, at least, is drive home the fantasy of Carolyn Bessette-Kennedy; the far-away idea of who she was and the world she occupied. Intriguingly, this has little to do with who she married. In modern Bessette-Kennedy fan circles, JFK Jr is merely an accessory – a gorgeous lunk attached to a Nineties trendsetter. Often JFK Jr is best read in that context.

The strongest parts of Terenzio and McNeil’s book are the memories of a pre-fame Bessette-Kennedy barrelling through a long-ago Manhattan, working as a publicity director at Calvin Klein by day and partying by night. “She was a club girl, and she dated a lot of people,” recalls Brian Steel, a friend of JFK Jr’s. Terenzio, who became close with the couple, remembers Bessette-Kennedy living in a brownstone apartment in the West Village before she moved in with JFK Jr. Kate Moss was her upstairs neighbour for a time. There are memories of Bessette-Kennedy smoking Parliament Lights at Tribeca sushi restaurants, doing recreational cocaine, and taking shopping trips to Neiman Marcus.

“She was pretty enigmatic in the sense of… who is this wild person?” recalls Robbie Littell, a JFK Jr friend. Another pal, Jack Merrill, adds: “She was able to get dirty. She and John understood that sometimes there has to be a little grime to have a good time.” Many contributors describe her in similarly abstract terms – “electric”; “dynamite”; “that kind of girl”. Even how she and Kennedy met is slightly opaque. He tells a friend they first encountered one another “at Calvin Klein” in 1992. Their relationship timeline is messy; Kennedy seemed to be simultaneously dating Carolyn and actor Daryl Hannah for a while before the pair became official in 1994.

As the book continues, Bessette-Kennedy becomes more hazy as a figure. A physical fight between the couple, caught on film while they were walking their dog through Central Park, is a national scandal in February 1996, but the book downplays it. “The fight was about him being taken advantage of by his friends,” Terenzio says. “John didn’t think it was a big deal. Carolyn was upset because they were being followed by photographers, and now a videographer. I think on some level she felt like it was her fault, but she was also angry at John because she felt she was trying to protect him.”

Their wedding that September only accelerates the press attention on her, which wears her down. Kennedy, meanwhile, was distracted by the high-profile launch and subsequent sales struggle of his lifestyle magazine, George. “Carolyn’s life disappeared,” her friend Sasha Chermayeff recalls. “She’s this fabulous girl … but her identity completely changed. She went from being the coolest girl in her circle but not famous to being completely famous and subject to the whims and insults slung by the tabloid media.”

Chermayeff says that over time this only worsened, with Bessette-Kennedy becoming increasingly fearful of the press and her marriage becoming strained. Others claim that she barely left the house. “One thing about Carolyn, she knew the answers,” Chermayeff says. “This is how you look good in New York. This is what you say to a guy when he’s being a dick. This is what you tell your boss. But she could not bring all of that wisdom and point it at herself, to deal with her fears.” By the time of their deaths, she and Kennedy were contemplating divorce.

There is a sense throughout JFK Jr that nobody wants to go too hard on either party, likely out of sensitivity. Ask Not forgoes that approach, but to a slightly histrionic extent. There, Kennedy is described as a narcissistic “himbo” – a man “coddled and spoiled”, “prickly and impatient”, “something of a brat”. Callahan states that the only reason Carolyn put up with his arrogance, his filthy apartment and his bad habits was because she herself was a ruthless gold digger. That’s about the nicest Callahan gets about her. She claims Carolyn psychologically tormented her exes and relentlessly pursued JFK Jr until he was hers. Then her transformation into a “sleek Upper East Side ice queen” began.

“Her face grew hard and angular,” Callahan writes. “Her once unruly hair was heated and ironed straight, her scalp scorched and pulsating under the bleach, the burns cooled into hard, raised scabs underneath that platinum mane.” She makes her sound like Frankenstein’s monster.

The plane crash that killed the couple, along with Carolyn’s sister, Laura, was officially blamed on Kennedy’s piloting skills – he was only trained to fly during clear weather and succumbed to spatial disorientation during a short flight to Martha’s Vineyard. But Callahan suggests the crash spoke to Kennedy’s arrogance and his penchant for self-destruction. “Was there a part of him, subconscious or not, that didn’t care if he died, taking his wife and sister-in-law with him?” she coolly asks. “His magazine was on the verge of collapse. His marriage was failing. His sister was barely talking to him. His life was coming apart on all fronts.”

Neither book necessarily feels like the full story. Bessette-Kennedy and JFK Jr were tempestuous and erratic, but most importantly private. Their secrets died with them. But the effect here doesn’t harm the myth that surrounds Carolyn herself. That image she had – the slip dresses and turtlenecks, the understated glam – is all retained. Beautiful, photogenic, yet always unknowable. Forget the Kennedys: Carolyn Bessette’s mystery is her greatest legacy.

“When I think of my wife, I always think of her head and what’s inside it,” muses Ben Affleck in his 2014 thriller Gone Girl, which cited Bessette-Kennedy as one of the key inspirations for its cryptic quasi-villain, Amy Dunne. “I think of that too: her mind, her brain, all those coils, and her thoughts shuttling through those coils like fast, frantic centipedes … What are you thinking? How are you feeling? Who are you?”

‘JFK Jr’ and ‘Ask Not: The Kennedys and the Women They Destroyed’ are available now