Inside Carolyn Bessette's Final Days: Heartbreaking Revelations About Her Life With John F. Kennedy Jr.

In no variation of this world was Carolyn Bessette not going to be met with a bizarre combination of reverence and resentment.

She had dared to be the woman John F. Kennedy Jr.—one of the most eligible bachelors on the planet, the closest thing America had to a crown prince—fell in love with and eventually married. And, in a way, she would never be forgiven for taking him off the market.

No matter that Carolyn and John did not live happily ever after, instead dying in a plane crash on July 16, 1999, that also killed her sister Lauren Bessette. Their story has thereby been impossible to tell from any angle without an ominous tinge shading even their happiest moments. 

In death, Carolyn didn't exactly become an afterthought in the wake of all the rabid attention—explained away as public interest—that was paid to her during the seven years she was linked to the only son of President John F. Kennedy and Jacqueline Kennedy. But her personhood was gobbled up by history, dragged under the weight of the overwhelming tragedy of it all.

Not willing to lose Carolyn to time as the 25th anniversary of her death at 33 approaches, or to let her be filed away as merely a style icon, Elizabeth Beller seeks to reclaim the woman who existed outside of John's aura in her new book Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy.

The biographical basics about the 5-foot-10 Boston University graduate—even before she was tasked in the spring of 1992 with overseeing a private VIP fitting for the Camelot heir at the Calvin Klein boutique at Saks Fifth Avenue—are, of course, well documented.

And there's a not-small library's worth of books dedicated to the Kennedys, with John alone commanding his own section thanks to the millions of words telling his story and how it ended. A confluence of pedigree and personality traits led to the fatally irresponsible decision to pilot his six-seat Piper Saratoga away from the lights of the shoreline in order to save 10 minutes on the way from New Jersey to Martha's Vineyard.

But Once Upon a Time is about her, and plenty of people who knew her wanted to talk about the woman who—unlike Princess Diana, the doomed public figure she's most compared to (not least because John told a friend Carolyn was "spooked" by the royal's 1997 death)—never got to share her side of the story.

Plenty of media outlets would have salivated over the prospect of an in-depth sit-down with Carolyn, but she had no interest in baring her soul. Rather, she died while still trying to figure out what to do with the life she'd been ridiculed for daring to object to after willingly signing up for it.

A recurring theme throughout the book is time, as in, if she only had more of it, who knows what would have happened? Even if the imminent-divorce rumors had been true, the friends who knew her and John both separately and together generally conclude that they would have figured it out.

Because that is what time allows, and Carolyn and John had so little of it. 

Which is why even a Carolyn-centric narrative, while it salvages her oft-maligned character from the scrap heap of so-called difficult women, is still relentlessly heartbreaking. Here are the most haunting revelations about Carolyn's final days from Once Upon a Time: 

Carolyn Bessette was inarguably a trendsetter during her life, from her effortless downtown ensembles of long skirts, snug white tees and Chuck Taylors that turned heads during her days in sales and PR at Calvin Klein, to her impeccable Narciso Rodriguez silk crepe wedding dress, to the parade of flawless monochromatic looks she chose for events once she was the toast of society with John F. Kennedy Jr.

The admiration for her style has only evolved into worship since she died in a plane crash with her husband and sister Lauren Bessette on July 16, 1999.

But she didn't just add a little polish to her innate flair once she entered the Kennedy orbit, according to Elizabeth Beller's 2024 book Once Upon a Time.

Rather, Carolyn changed to meet the standards of what she thought John's late mother Jacqueline Kennedy would have wanted for her only son.

After a heady summer romance in 1992, John unceremoniously broke it off after a friend sent him a letter detailing why Carolyn was bad news. She resisted his efforts to apologize for more than a year, even changing her phone number.

So John, also entangled with off-and-on girlfriend Daryl Hannah during this time, never introduced Carolyn to his beloved mom before she died of non-Hodgkins lymphona on May 19, 1994—one of his great regrets and a reason Carolyn gave for breaking up with him several times.

But the world knew Jackie was synonymous with taste and elegance. In February 1996, Carolyn went from light brunette with highlights to the cornflower blonde hair she was known for, courtesy of colorist Brad Johns, started plucking her eyebrows ultra thin and lost weight from her already willowy 5-foot-10 frame.

"All of it" wasn't the real Carolyn, longtime friend MJ Bettenhausen told Beller, but "eventually she would have centered. She was always fit and had a beautiful figure, but she became so thin and pale…I think she felt she had to fit in, to be what she thought people expected a Kennedy to be."

In 1997 Carolyn started regularly wearing designer Yohji Yamamoto. She looked invariably fabulous, but the neutral colors and sleek silhouettes (he made "clothing like armor," he noted in the 1989 documentary Notebook on Cities and Clothes, to "protect the clothes from fashion" and "the woman's body from something") may have been her way of trying to hide in plain sight.

Which was impossible, but she was sick of all eyes being on her, always.

Carolyn "would have laughed at being called a fashion icon," her friend Michelle Kessler told Beller. "She was trying to be nothing of the sort. Carolyn was trying to have an interesting life and go about her day without interruption."

It wasn't just posthumously that everyone knew John and Carolyn's address. She had already moved several times since meeting him in 1992—from the East Village, where she first lived upon moving to New York from Greenwich, Conn., in 1989, to Greenwich Village in 1993 when paparazzi started staking out her apartment, and then to new West Village digs in 1994 after they tracked her down again.

Carolyn moved into John's Tribeca loft with no doorman and no security at 20 North Moore in 1995.

While John and countless others assured her that the paps would chill out once they were married, the photographers waited outside for her every morning. And by many accounts, the coverage of their relationship—feverish and intrusive as it was before—only got worse.

In the media's eyes, John had always been a generous public figure as he rollerbladed or bicycled around town, romanced stars like Daryl and Madonna, and accepted press attention as part of his life. So when he asked them to give his girlfriend, and then wife, a break—sometimes with daggers in his eyes, another time jumping on the hood of a photographer's car—Carolyn ended up blamed for the dip in his tolerance.

As Beller notes, it apparently didn't occur to the press that John's hackles were up because he loved Carolyn, who was so obviously distressed, and wanted to protect her.

Other than never really enjoying having her picture taken, even as a teenager, Carolyn's increasingly reclusive ways were the antithesis of her actual character.

According to friends in the book, she didn't like to be alone and was always on the go during her single days. She was described as a fiercely caring friend who'd be first at the hospital if someone was sick or who would call because she'd seen a look on a colleague's face earlier in the day and guessed correctly that she needed someone to talk to. 

A "super empath," friend Michelle called her. (Though she also flirted with an out-of-town colleague's boyfriend when she needed a confidence boost, according to an unnamed pal, but apparently felt bad enough to never do it again.)

As she grew warier of leaving the house because of the photographers who could make five-figures from one picture—and the sadder or angrier she looked, the more lucrative the payday—multiple people invoked a similar metaphor for what those days were like for her.

MJ said Carolyn felt like "a caged animal." And John's friend and former Brown University roommate Chris Oberbeck told Beller that the more she retreated, the nastier the press got, leaving Carolyn "like a tiger in its cage; pacing back and forth and understandably angry."

As Beller points out, even the non-tabloid media (seemingly every newspaper, from the Washington Post and the New York Times to the Detroit Free Press and the Spokane, Wash. Spokesman-Review was on the gossip beat) had instances of treating Carolyn like a very unserious person, her substance unapparent and her career in fashion a little louche for John's blue blood.

An Oct. 6, 1996, NY Times op-Ed speculated as to whether she would have met not just Jackie's standards, but appearance-conscious family patriarch Joe Kennedy's—as if the Kennedys weren't known just as much for scandal as they were being a powerful political dynasty.

The argument actually concluded that Carolyn was a perfect match for "a pleasant young man who also has a talent for promotion," so in the end, everyone was complicit in the cultural degradation.

Carolyn had worked at some job or other since high school, and in three years went from VIP sales at Calvin Klein's Saks Fifth Avenue boutique to becoming director of PR for the Calvin Klein Collection in 1992.

But she resigned from Calvin Klein after seven years in March 1996. A couple of weeks beforehand she and John had a drawn-out fight in Washington Square Park that was recorded for all of America to watch in nightly segments and turned into an 11-page spread in the National Enquirer.

Aside from not wanting to be a distraction from the brand, Beller writes, "It had become increasingly impossible for her to walk into the office due to the stalking paparazzi's presence."

Former Improper Bostonian reporter Jonathan Soroff told Beller that he ran into Carolyn at an event and she told him she'd love to be working but couldn't anymore, that "'life has become a circus.'"

Carolyn did serve as one of John's closest—albeit unofficial—advisors as he prepared to open his magazine George, but she didn't want to detract from his passion project and even stayed away from the Sept. 7, 1995, launch so that the moment would be his and not about her and them.

And then came the era of What-does-Carolyn-do? coverage.

A question she also asked herself, according to many friends, including Carole Radziwill, who had no doubt she would've found her next calling, if only allowed the time. The daughter-in-law of Jackie's sister Lee Radziwill, Carole was married to John's best friend and cousin Anthony Radziwill for five years until his death from cancer in August 1999. (John had been writing Anthony's obituary before he died, but Anthony ended up reading Psalm 23 at John and Carolyn's funeral.)

In Beller's book, Carole, who was working at ABC News at the time, recalled talking to Carolyn about documentary filmmaking in the spring of 1999 and thinking that could be a promising road for her friend. The Real Housewives of New York City alum said Carolyn also expressed interest in going back to school to study psychology, "making use of her innate talent at homing in on the heart of someone's troubles and uplifting them."

For most of her time in the public eye with John, Carolyn didn't hide her aversion to the press, turning her gaze downward (like the similarly hounded Princess Diana, Beller notes) as she made her way into events and not bothering to force a smile. She also eschewed the advice she got from John and others to appease the paparazzi by posing for one good shot to get them to go away.

The more she resisted, the more the photographers got in her face (some yelled vile slurs at her to elicit a reaction) and the more she was portrayed as difficult or cold.

While the first suggestion of pregnancy was raised and shut down as early as March 1996, Carolyn seemingly spent the entirety of her marriage—basically the last 34 months of her life—as the subject of bump speculation.

"Carolyn 'Bassinet' Kennedy," read one headline when she and John returned from a trip to Italy (during which they had to switch hotels to elude paparazzi) in June 1997.

Friends painted Carolyn to Beller as a real baby whisperer type who loved children. She got her degree in education from Boston University and at one point considered being a preschool teacher, but, as she reportedly told Women's Wear Daily in 1992, she felt that teaching ultimately wasn't "provocative enough" for her.

While tabloids put the no-children-yet onus on Carolyn as the years went by, she was admittedly scared of bringing a child into the mix when she couldn't even cross the street without cameras in her face. Moreover, John was putting work first, spending long hours at George and traveling constantly to meet with potential investors and advertisers.

But friends told Beller that, in the months before they died, John and Carolyn were working on their marriage and spoke of having children.

The fall and winter of 1997 were a particularly fraught time for John and Carolyn, Beller notes, with tabloids reporting they were fighting constantly and on the verge of divorce.

Eventually the rumors of marital troubles caused actual marital troubles, and by early 1998, Beller writes, Carolyn was "falling apart" and, according to John's longtime friend Jack Merrill, "in the midst of several crises."

Carole described what was happening to Carolyn as a sort of "gaslighting," that constantly hearing from people who are trying to find out if what they just read about you is true "interrupts the navigation of these relationships...and you can find yourself as confused as the tabloids are."

Friends Carole, MJ, Michelle, Hamilton South and Betsy Reisinger Siegel all scoffed at the persistent rumor at the time that Carolyn was having an affair with an ex-flame.

She "would have never jeopardized her marriage by an affair, she was way too smart for that," Michelle told Beller, while Carole and Hamilton just laughed, according to the author.

Multiple people in the book also said that, while Carolyn loved to have a good time, they never saw her drink more than a few glasses of wine or dirty vodka martinis. And everyone quoted said they never saw her use drugs, contrary to rumors from that time that she was doing a lot of cocaine in 1998. 

One of the most tragic elements of Carolyn's story—her own and the one she shared with John—is simply that everyone who knew her, no matter how depressed she was by the press and how uncertain she was about the long-term health of her marriage, was confident that she was going to be just fine…eventually.

What could have been a blip—he was always working, they had trust issues—turned into the totality. Maybe their problems would have proved insurmountable. Or perhaps they would have powered through.

Either way, the roller coaster became their forever story.

Friends told Beller that Carolyn was starting to find herself again in the last year of her life.

She started to spend more time at sister Lauren's apartment a few blocks away, even spending the night occasionally, according to Bessette family friend William Peter Owen. As Beller writes, "The message seemed to be: I still have my own life. Take me for granted, and I won't be there."

And in early 1999, Carolyn—who, wary of hangers-on and faux friends who didn't have John's best interests at heart, never stopped being her husband's No. 1 supporter—returned to the George offices. She had stayed away for almost two years, not wanting to interfere while her husband tried to keep the struggling publication afloat.

She had even, as dutifully noted by the press, started smiling again when she was out.

Nothing is more heartbreaking than recalling Carolyn and John's happiest moments, the times when they were truly able to enjoy each other without feeling intruded upon or compelled to perform for the public.

Case in point, their candlelit Sept. 21, 1996, wedding ceremony in front of only 40 guests on Cumberland Island, the spot so low-key the church didn't even have electricity.

Gustavo Paredes, the longtime manager of the Hyannis Port house Jackie left John and his sister Caroline Kennedy, recalled how John told him in the summer of 1994 that he'd never believed in stories about meeting "the one," that such an "instant connection doesn't happen in real life."

Then, Gustavo said, John added, "Well, that happened to me."

His daughter Ariel Paredes told Beller, "They would love hard and they would fight hard, but they were very much a couple."

Friend Betsy said that photos from her March 1998 wedding in Miami showed that "Carolyn and John were deeply in love, and in love with life. That is how I remember them, when they felt safe."

On July 18, 1999, when officials announced the search for John's plane had gone from a rescue to a recovery mission, 20 North Moore turned into a shrine.

With Carolyn never to emerge again, photographers instead took photos of the candles and flowers piled outside the front door and the horde of people who made a pilgrimage to Tribeca to pay their respects.

Even those who were privy to the issues Carolyn and John were having told Beller that it took years—long after the couple were gone—to really get what the once-private person caught up in Kennedy mania went through.

"At the time, it could seem like she was blowing it out of proportion," said Sasha Chermayeff, a longtime friend of John's who ended up close to Carolyn too. "Even her closest friends and husband sometimes couldn't see it for what it was."

Sasha continued, "Everyone thought, Come on, figure this out… Only in hindsight, from this perspective now, I see that no one was really fully there for her in that way. That proved to be further isolating for her, compounding her fear and anger, but her anger was healthy given the situation."

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For more stories about Carolyn Bessette-Kennedy's life, get a copy of the book.