Death of Carolyn Bessette Kennedy: Still a beautiful mystery 25 years after her tragic plane crash

Ts are just two known recordings of fashion icon Carolyn Bessette-Kennedy's voice. One is eight seconds long. (“It was a very exciting and wonderful evening,” she tells a reporter on the red carpet at a 1998 ball.) The other is barely two seconds long. It is deep and elegant. Almost musical. A voice for gala receptions and charity dinners, for talking 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 teenagers born long after the 1999 plane crash that killed her and her husband, John F. Kennedy Jr. – study these clips. They also study photos of her – the clean lines of her wardrobe, the icy blond of her hair, that unmistakable aura of a woman at once beautiful and doomed. She is a mystery to be solved. Answers are rarely forthcoming.

That hasn't been much of a problem in the 25 years since Bessette-Kennedy's death. One of the great enigmas of late 20th-century American celebrity, she popularized a kind of quiet luxury long before “quiet luxury” became a fashionable term. Think minimalist separates, black sandals, oversized white shirts. Very chic. Very tailored. Very Calvin Klein, where she worked as a PR agent before getting married. She is one of the beacons of the “Flashback Friday” genre on social media – images from the archives representative of a seemingly distant and more innocent past. And if not more innocent, then at least more entertaining. That she died so young and so tragically, aged just 33, only added to her mythological appeal.

Two new books claim to fill these gaps. JFK Jrby 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 would seemingly make him as famous as his parents, President John F. Kennedy and Jacqueline Onassis. Don't Ask: The Kennedys and the Women Who Destroyed Themby journalist Maureen Callahan, is as lurid as its title – a condensed version of the sexual nightmares in the Kennedy White House and beyond. Both are touted as definitive retellings and both devote a lot of time to Bessette-Kennedy, her glamour and her diversity. But where JFK Jr is always a bit too clean, Don't ask is too offensive. It makes Bessette-Kennedy even more unknown. She is either an aloof martyr or a drug-addicted upstart. You can't come away the wiser.

What JFK Jr does at least to feed the imagination of Carolyn Bessette-Kennedy; the far-fetched notion of who she was and the world she lived in. Interestingly, this has little to do with who she married. In modern Bessette-Kennedy fan circles, JFK Jr. is merely an accessory – a beautiful guy tied to a nineties trendsetter. Often JFK Jr is best read in this context.

The strongest parts of Terenzio and McNeil's book are the memories of a Bessette-Kennedy who, before her fame, roamed the Manhattan of the past, working as a public relations director at Calvin Klein by day and partying by night. “She was a club girl and went out with a lot of people,” recalls Brian Steel, a friend of JFK Jr. Terenzio, who became close to the couple, remembers that Bessette-Kennedy lived in a West Village brownstone apartment before moving in with JFK Jr. Kate Moss was her upstairs neighbor for a time. There are memories of Bessette-Kennedy smoking Parliament Lights at sushi restaurants in Tribeca, doing cocaine recreationally and making shopping trips to Neiman Marcus.

“She was quite enigmatic in the sense that … who is this wild man?“, recalls Robbie Littell, a friend of JFK Jr. Another pal, Jack Merrill, adds: “She could get dirty. She and John understood that sometimes you need a little dirt to have fun.” Many contributors describe her in similarly abstract terms – “electric”; “dynamite”; “The kind of girl.” Even how she and Kennedy met is a bit unclear. He tells a friend that they met “at Calvin Klein” in 1992. The chronology of their relationship is messy; Kennedy seemed to be dating Carolyn and actor Daryl Hannah at the same time for a while before the relationship became official in 1994.

As the book progresses, Bessette-Kennedy becomes increasingly murky as a character. A physical altercation between the couple, caught on film as they walked their dog through Central Park, is a national scandal in February 1996, but the book downplays it. “The altercation 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 like she was trying to protect him.”

Her wedding in September only increases the press attention on her, which is wearing her down. Kennedy, meanwhile, has been distracted by the high-profile launch and subsequent sales difficulties of his lifestyle magazine. George“Carolyn's life disappeared,” recalls her friend Sasha Chermayeff. “She's this fabulous girl… but her identity changed completely. She wasn't the coolest girl around, but she wasn't famous, but she became an absolutely famous woman, subject to the whims and insults of the tabloid media.”

Chermayeff says the situation only got worse over time. Bessette-Kennedy became increasingly afraid of the press, and her marriage was in crisis. Others say she rarely left the house. “One thing about Carolyn was that she knew the answers,” Chermayeff says. “That's how you make a good impression in New York. That's what you say to a guy when he's acting like an asshole. That's what you say to your boss. But she couldn't apply all that wisdom to herself to deal with her fears.” When they died, she and Kennedy were considering divorce.

There is a feeling everywhere JFK Jr that no one, probably out of consideration, wants to judge either party too harshly. Don't ask eschews this approach, albeit to a slightly theatrical extent, describing Kennedy as a narcissistic “himbo” – a “pampered and spoiled,” “prickly and impatient,” “something of a brat.” Callahan states that Carolyn only had to put up with his arrogance, dirty apartment, and bad habits because she herself was a ruthless gold digger. That's about the nicest thing Callahan says about her. She claims that Carolyn psychologically tormented her ex-boyfriends and relentlessly pursued JFK Jr. until he was hers, then began her transformation into a “stylish Upper East Side ice queen.”

“Her face became hard and angular,” Callahan writes. “Her once unruly hair was heated and ironed flat, her scalp was seared and pulsing under the bleach, the burns cooled to hard, raised scabs beneath the platinum mane.” She makes her sound like Frankenstein's monster.

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

None of the books necessarily feel like the whole story. Bessette-Kennedy and JFK Jr. were tempestuous and unpredictable, but above all, private. Their secrets died with them. But the effect here does not detract from the myth surrounding Carolyn herself. Her image – the slips and turtlenecks, the understated glamour – all remains intact. Beautiful, photogenic, but always inscrutable. 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 in it,” muses Ben Affleck in his 2014 thriller GoneGirlwhich Bessette-Kennedy cites as one of the main inspirations for his cryptic quasi-villain Amy Dunne. “That's what I think about too: her mind, her brain, all those convolutions and her thoughts darting through those convolutions 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 now available