The Complicated Reality of JFK Jr. and Carolyn Bessette’s Relationship

Tyler Henry Unknowingly Connects to Carolyn Kennedy in Carole Radziwill Reading

Carolyn Bessette didn’t say yes when John F. Kennedy Jr. first proposed to her.

She didn’t say no, either, but remarkably the 29-year-old Calvin Klein publicist, who had been dating the eligible bachelor for about a year (after several years of the run-around), wasn’t yet sure that she was ready for what marrying him would entail. Namely, a merging of lives that would come with a host of perks but also require a daunting amount of self-sacrifice, not even including the matter-of-fact assault on her privacy.

Carolyn had spent enough time at the Kennedy family compound in Hyannis Port to know that there was no exaggerating the legend behind the larger-than-life name, a family technically made up of flesh and blood just like any other but which had embedded itself in the very fabric of American culture over the greater part of the 20th century.

And she wasn’t bowled over by the Kennedy bond. Rather, the clannishness turned her off.

Carolyn loved John, but in what would become a point of contention for the rest of their lives, she didn’t particularly enjoy going to spend holidays and weekends with his sprawling family on the Cape, where their comings and goings were rather formally presided over by reigning matriarch Ethel Kennedy, Robert F. Kennedy‘s widow, and the Kennedy men, who with their touch football games and clambakes seemed lifted from a Ralph Lauren ad.

She wasn’t exactly culturally adrift, having been born in White Plains, N.Y., and raised in posh Greenwich, Conn., by her mother and orthopedic surgeon stepfather, but she still felt like an outsider. And on the beach of Hyannis Port, Carolyn witnessed John being a cog in the Kennedy machine, rather than the dashing man about town he was in New York. Independent and confident on her own, being around the Kennedys made the 5-foot-10 beauty feel small and insecure.

“We don’t do insecurity very well,” John told his childhood friend Gustavo Peredes, whose mother, longtime Jacqueline Kennedy Onassis aide Providencia Paredes, was close to the young couple. “That’s definitely not on the Kennedy menu.”

Red flags aside, though, he was still JFK Jr.

So, about three weeks after People‘s Sexiest Man Alive circa 1988 first popped the question over Fourth of July weekend on Martha’s Vineyard, she did finally accept.

“I actually think that made John even more eager to marry her,” RoseMarie Terenzio, John’s executive assistant starting in 1994, told The Kennedy Heirs author J. Randy Taraborrelli.

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How Did John F. Kennedy Jr. and Carolyn Bessette Meet?

John met Carolyn in 1992 when she was called upon to oversee a VIP Calvin Klein fitting for the former first son. And he was instantly smitten. 

“Early on, he would be frustrated,” attorney Brian Steel, who met John when they both worked in the Manhattan District Attorney’s office, recalled in the 2018 ABC News special The Last Days of JFK Jr. “He would say, ‘I called her and she hasn’t called me back.’ And John did not like that.”

Gustavo told People in 2014 that Carolyn “didn’t think he was serious. He couldn’t believe she turned him down. It had never happened before.”

“She was exactly the kind of girl I imagined would date someone like John Kennedy Jr.,” RoseMarie recalled in her 2012 book Fairy Tale Interrupted, “and she intimidated the hell out of me.” When she first met Carolyn, though, RoseMarie could tell she “was different from the typical gorgeous girls you see around Manhattan. She wasn’t trying too hard. She wasn’t trying at all.”

Carolyn was playing it cool, but she was acutely aware of who John was. “I kept having to say, ‘Snap out of it, he’s just a guy,” she told the future Carole Radziwill (née DiFalco), who was about to marry John’s cousin and best friend Anthony Radziwill in August 1994.

“Carolyn was also worried marriage would change everything,” RoseMarie wrote. Carolyn had already moved into John’s spacious loft at 20 North Moore St. in TriBeCa, but “she understood that the formality meant something, especially to John and his lifestyle. He was pretty old-fashioned, and given his place in the world, he couldn’t be single forever.”

John had certainly never wanted for female company, having romanced the likes of Daryl Hannah, Sarah Jessica Parker and Madonna, but by the mid-’90s the crown prince of the fallen kingdom of Camelot did want a true partner by his side.

Ron Galella/Ron Galella Collection via Getty Images

He was at least partly motivated to take that next step by grief: His mother, who he was extremely close to, died in May 1994 and, in the summer of 1995, Anthony was given a dire prognosis when the testicular cancer he successfully battled in the 1980s returned.

So, after a year of being with Carolyn, he was ready to seize the day, in more ways than one. That September, with his fiancée by his side, John announced the launch of his glossy magazine George, a publication he envisioned would uniquely meld the worlds of politics and celebrity that were already inextricably linked. Cindy Crawford, dressed as George Washington and photographed by Herb Ritts, famously graced the cover of the inaugural October/November 1995 issue.

“It felt like a victory not just for John, but for Carolyn,” Richard Bradley, who served as executive editor at George (and went by Richard Blow in those days), was quoted in The Kennedy Heirs. “She was excited about John, about his drive and determination and the fact that he’d found something that gave him purpose. She wanted to be with him the whole way. She told me she had a sense that this was the first of a series of magazines John might publish, and she had an idea about a style magazine for men, something like Esquire but more mainstream.”

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“When you were with them,” Richard continued, “you felt John had really put forth a new power couple in the family, and there had been a lot of them, like Jack and Jackie, Bobby and Ethel, Sarge and Eunice [Shriver]. John had always had a thing about the Kennedy power couples of the past, and this was how he wanted to view himself and Carolyn. So, I guess one could say that Carolyn was becoming the woman behind the man, and John was happy and proud about it. I think his mom would have been as well.”

And importantly for Carolyn, who did her best to ignore the women of all ages who shamelessly threw themselves at her fiancé, John wasn’t too old-fashioned. Unlike so many of the men in his family, including his late father, President John F. Kennedy, he aspired to take their relationship, and their eventual marital vows, seriously.

“I see what goes on in this family, and it scares me,” Carolyn had admitted to her friend Stewart Price, according to The Kennedy Heirs. He reminded her that John was different, to which she replied, “It’s a good thing, too. I know myself and I’m definitely not that pathetic Kennedy wife who’ll stay home with the kids while her husband is out screwing around. No. I’m that pissed-off Kennedy wife who’ll be in prison because she took matters into her own hands.”

Poet and Grateful Dead lyricist John Perry Barlow, a close friend and mentor to John since the 1970s, recalled the young man saying that he didn’t want to be “‘that creepy Kennedy who doesn’t care what his girl thinks about anything. I hate those guys.'” 

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What Did Carolyn and JFK Jr. Fight About?

So though numerous issues would plague John and Carolyn’s relationship in the months and too-few years to come, by all accounts infidelity wasn’t one of them—though, according to some, Carolyn would tell John during fights that she was seeing an ex-boyfriend.

Her friends didn’t think she would actually cheat, though.

“Carolyn, more than anyone who John had been with, would stand up to him, and confront him, and I think that John to an extent needed that,” historian Steven M. Gillon, a classmate of John’s at Brown University who was later a contributing editor at George, told InStyle in 2019.

That being said, John was still a headstrong Kennedy, possessed of an explosive temper that wasn’t usually mentioned in the rapturous accounts of the political scion’s inimitable charm and infinite potential—though his ex-girlfriends knew better. 

The National Enquirer had a field day when he and Carolyn were photographed and, worse yet, caught on video heatedly arguing in Washington Square Park on Feb. 25, 1996. They had been walking their dog, Friday, when, according to onlookers, they started screaming at each other.

She shoved him and John grabbed her wrist and tried to pull Carolyn’s engagement ring off of her finger. She was holding Friday’s leash and according to various reports—including the New York Daily News synopsis headlined “Sunday in the Park With the George Editor”—he yelled, “You’ve got my ring, you’re not getting my dog!”

John sat down on the curb in apparent anguish and Carolyn knelt down to console him, after which they left the park hand-in-hand.

“From a public relations standpoint where George was concerned, the fight was very bad,” Richard Bradley recalled. “We were afraid of how it would affect advertisers, especially women’s fashions and cosmetics. I know John regretted it, but unfortunately it was Carolyn who suffered the most in the court of public opinion. On the video, she definitely looked like the aggressor. It helped to set in stone an unflattering image of her as being dramatic and unhappy. We all knew John had a temper, but the public didn’t.”

“It looked like Carolyn had brought out the worst in America’s prince, that she was changing him, and a lot of people held that against her,” he continued. “In the end I think Carolyn was more angry at herself that she’d left John get to her in public than she’d been at whatever they were arguing about.”

Isn’t that always the way? To his many admirers still probably smarting from JFK Jr. being yanked off the market by this…this…woman, Carolyn was both heroine and villain, the princess-to-be who had won the prince’s heart but who was already causing him great heartbreak. And hadn’t this family been through enough?

Never mind what Carolyn was facing on a daily basis with the paparazzi, which waited for her outside her building and would do and say anything to get a rise out of her. John, who used to have a little fun with the photographers by wearing a dress and a lady’s wig so they wouldn’t notice him whizzing by on his bicycle, told Carolyn to just relax and ignore them. Autograph seekers and camera flashes had been part of his daily life forever, after all.

Friends of the couple encouraged Carolyn not to engage with the press—don’t worry if they call you names, you can’t win either way, they advised her—and equally encouraged John to be more sensitive to Carolyn’s concerns. After all, she didn’t grow up with that life.

At the same time, however, the rumor that John had hit Carolyn in the park was spreading like wildfire, even ending up the topic of one of David Spade‘s “Hollywood Minute” segments on Saturday Night Live.

“Why don’t you stop hitting your girlfriend and pretending to run a magazine?” Spade cracked.

“I knew that John had a temper and that Carolyn was no shrinking violet,” Bradley recalled in his 2002 best-seller American Son: A Portrait of John F. Kennedy Jr. “But the violence of their rage [as evidenced by the video] presented a harsh contrast to the tenderness I’d seen between them.” 

“They were fiery,” Ariel Paredes, Gustavo’s daughter and a good friend of Carolyn’s, remembered to People in 2014. “They would love hard and they would fight hard but they were very much a couple.”

Russell Turiak/Getty Images

Gillon wrote in his 2019 book America’s Reluctant Prince: The Life of John F. Kennedy Jr., “The cause of this infamous fight, and the many that followed, stemmed from Carolyn’s ongoing complaint that John let people walk all over him.”

In Carolyn’s eyes John was too much of a yes-man when it came to people asking for favors, and according to Gillon she was still mad about a wedding they had recently attended for a couple they barely knew, where it became obvious to her that the groom had finagled New York Times society page coverage by asking her husband to be his best man.

“She may or may not have been right,” Gillon continued, “but she was furious at John for not making a statement by walking out. It was a familiar argument, one she had belabored frequently in private, but this time it leaked into public view.”

Meanwhile, count John’s sister, Caroline Kennedy Schlossberg, among his many family members who thought the fight in the park was a bad sign. No fan of Carolyn’s in the first place, Caroline thought, according to Taraborrelli, that her future sister-in-law should have known to “avoid those triggers while in public.”

Their uncle, Sen. Edward Kennedy, “spoke to John about it to sort of parent him through it, but he told me he didn’t get far because the kid was so shaken and embarrassed,” the late Sen. John Tunney once said about the incident. “This kind of thing reflected poorly not just on John, but on the entire Kennedy family. Also, Ted knew John wanted to be taken seriously as a businessman with George. What had happened had been at odds with the image he was hoping to project in that regard.”

Though John hadn’t entirely ruled out going into politics down the road, George was his baby, something he was determined to pull off on his own (along with business partner Michael Berman).

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But as many a Kennedy has noted over the years, not a single person has been born into the family—especially not the guys—without eventually feeling the crushing weight of expectations and history upon them.

“People keep telling me I can be a great man,” John, determined to forge his own path, once said. “I’d rather be a good one.” 

Again, however, he was still JFK Jr.

So Ethel decided to have a chat with Carolyn after their little blowup in the park, and she sent a plane to pick up her nephew’s fiancée and bring the young woman to Hickory Hill, the RFK family estate in Virginia.

Did Ethel Kennedy Save JFK Jr. and Carolyn’s Relationship?

Widowed at 40 in 1968 and left to raise 11 children, Ethel sought to infuse her nephew’s insecure partner with some of her own hard-fought stoicism. She certainly understood what it felt like to exist in the shadow of a man’s overwhelming presence.

“I went through that with Bobby at first,” Ethel said, according to the unnamed friend who Carolyn brought with her to Hickory Hill that day for moral support, who shared the story with Taraborrelli. “Then I finally got it that the only way to survive in this family is to look in the mirror in the morning every single day and say, ‘You know what? I am enough.’ Plain and simple. That’s it. ‘I am enough.’ Eventually it sinks in that, yes, you are enough, and that no one can ever take that away from you. Not even the Kennedys.”

Evan Agostini/Liaison

Ethel also said, according to this witness, “Carolyn, I will tell you what I’ve told my daughters and my daughters-in-law. Be there for your husbands, but do not let them influence you into bad behavior. They will bait you. They always do. I’ve seen it for years. But you can’t take the bait. You must be stronger than that.”

Translation: No more screaming at each other in public, period. 

“Never in public,” Ethel pressed. “These men are hotheads. Don’t let them goad you into acting improperly in front of the whole world.” She also is said to have told Carolyn, “I think you’re more powerful than any of the other women John has dated. You know why? Because you’re smart, and because you have heart. So don’t let John or those reporters or photographers or anyone else change who you are in here.” She tapped Carolyn’s chest. “Do you understand?”

How Did JFK Jr. and Carolyn Bessette Pull Off Their Secret Wedding?

Though the press would never be any less relentless, JFK Jr. and Carolyn Besstte at least pulled off the wedding of the year without anyone aside from their closest family and friends knowing anything about it.

The couple tied the knot at First African Baptist Church on Cumberland Island off the coast of Georgia—reachable only by ferry, private boat or helicopter—on Sept. 21, 1996.

Richard Corkery/NY Daily News Archive via Getty Images

The Kennedys booked up all the rooms at the Greyfield Inn, the only hotel on the island, and rented a few private homes. Carolyn printed the wedding programs at the George office after hours, and RoseMarie helped with all the planning, including the setting up of a fake itinerary that would put John and Carolyn in Ireland that weekend. John personally called everyone a week beforehand to invite them to a party.

At one point a helicopter came into view as guests were leaving for the church, but after briefly circling overhead, it went away.

Carolyn wore an instantly iconic Narciso Rodriguez crepe silk slip dress and Manolo Blahnik heels. John wore a dark blue suit and his father’s watch. Caroline was Carolyn’s matron of honor (at John’s request), while her daughters Rose and Tatiana were flower girls and son Jack was the ringbearer. Anthony Radziwill was John’s best man. Sen. Ted Kennedy and John Perry Barlow were also among the 50 people who made the cut.

They enlisted trusted Kennedy wedding photographer Denis Reggie to chronicle their big day, and he’s the one who shot that one photo released to the press, of John kissing his bride’s hand as they left the church.

“The elegance and less being more and not making it a grand occasion but a warm and loving, memorable weekend—I thought that they pulled it off magnificently,” Reggie remembered to TODAY in 2021. Of the image he captured, “I thought there was a magic there. You can see in her face, in Carolyn’s face, surprise and elation and love and romance and all those wonderful things.”

On Sept. 23, 1996, a memo went out to the staff at George, as shared by the magazine’s creative director, Matt Berman, in his 2014 book JFK Jr., George, & Me:

“To: All the Gentlewomen and Gentlemen of George

“From: John

“Re: Breaking News

“I just wanted to let you all know that while you were all toiling away, I went and got myself married. I had to be a bit sneaky for reasons that by now I imagine are obvious.”

Dave Allocca/DMI/The LIFE Picture Collection via Getty Images/Getty Images

And so John F. Kennedy Jr. and Carolyn Bessette-Kennedy embarked on their next chapter together as husband and wife. 

But making it official didn’t change their clashing temperaments, their communication issues and certainly not the press’s consistently rabid interest in their lives, the paparazzi obviously hoping for a follow-up to their February 1996 performance in the park.

In July 1997, Carolyn went to Milan to attend the funeral for Gianni Versace, who had been murdered outside his Miami Beach mansion. Sitting right in front of her was Princess Diana, who John once had tea with at the Four Seasons in New York. The Princess of Wales had said no to being on the cover of George, but John was utterly charmed.

Five weeks after Carolyn briefly met Diana, the princess was killed in a car crash in Paris along with her boyfriend, Dodi Fayed. Their driver had been speeding through a tunnel trying to lose the paparazzi on their tail when he slammed into a pillar.

“I’m not sure what I’m going to do about Carolyn,” John told his friend Billy Noonan. “She’s really spooked now.”

According to America’s Reluctant Prince, Carolyn’s mother, Ann Freeman, had openly questioned during her wedding toast whether John was the right man for her daughter.

Anthony, however, tempered the awkwardness with his best man speech. “We all know why John would marry Carolyn,” he said. “She is smart, beautiful and charming…What does she see in John? A person who over the years has taken pleasure in teasing me, playing nasty tricks and, in general, torturing me. Well, some of the things that I guess might have attracted Carolyn to John are his caring, his charm, and his very big heart of gold.”

Carolyn had also become increasingly involved with George, much to the consternation of John’s partner, Michael Berman, who ended up selling his half of the magazine in 1997. Incidentally, Carolyn missed having her own career, but she wasn’t sure what she wanted to do—or could do, thanks to her outsized celebrity—next.

Then, in 1998, John, an adventurous outdoorsman who was always trying to go faster or higher or to somewhere more remote, took up flying—something his mother, when she was alive, had pleaded with him not to do.

“Please don’t do it,” Jackie told her only son, according to Christopher Andersen‘s The Good Son: JFK Jr. and the Mother He Loved. “There have been too many deaths in the family already.”

Two of President Kennedy’s older siblings, Joseph Jr. and Kathleen “Kick” Kennedy, were killed in air crashes in the 1940s, while Ethel Kennedy lost both of her parents in a plane crash in 1955 and, 11 years later, one of her brothers. Ted Kennedy had also been severely injured in a crash that killed two other people in 1964. Jackie’s stepson, Alexander Onassis, was killed in a crash shortly after takeoff in 1974. According to Maurice Tempelsman, Jackie’s partner for the last 14 years of her life, she had a premonition of John dying behind the controls of a plane.

As it turned out, Carolyn didn’t really want John to become a pilot either, and she never flew with him (and neither would Tempelsman or Ted Kennedy) without an instructor onboard. She knew how absentminded he could be—he was always losing his wallet or keys, she said—and she worried about his attention span. “I don’t trust him,” she unabashedly told a waitress at the Martha’s Vineyard airport café while waiting for her husband one day, per Andersen.

In May 1999, John crashed an ultralight powered parachute (basically a glider, but with a propeller) and broke his right ankle.

But six weeks later, still hobbling along on crutches, he was raring to fly himself and Carolyn to Hyannis Port for his cousin Rory Kennedy‘s wedding. With an instructor, of course.

Carolyn didn’t want to go. Her lack of enthusiasm about spending time with John’s family was among the many things that hadn’t changed over the course of their relationship, and she wasn’t particularly close to Rory, Bobby Kennedy’s youngest child, whom Ethel was pregnant with when her husband was assassinated.

“They had a pretty big argument over it,” a close friend of Carolyn’s told Taraborrelli in The Kennedy Heirs. “What was at stake for her was more than just getting her way. It had to do with respect, with being visible in her marriage, with being recognized… acknowledged. In a family full of loud voices, one thing Carolyn had learned about being around the Kennedys was that she had to speak up if she ever wanted to be heard.”

On July 12, 1999, John went to stay at the Stanhope Hotel on Fifth Avenue, while Carolyn took to sleeping in one of their loft’s guest rooms.


Was JFK Jr. and Carolyn Bessette-Kennedy’s Marriage in Trouble?

RoseMarie was worried what Carolyn’s absence from the wedding would look like to the outside world, yet another sign of trouble in paradise. She told John that he had to bring Carolyn with him. In her book, she wrote that she told her boss’ wife straight up, “Carolyn, are you f–king kidding me? What are you doing? You’re smarter than this. You don’t want to put John in a position where he has to explain where you are, and you don’t want to put yourself in a position of being judged. You get enough of that.”

RoseMarie and Carolyn’s sister Lauren Bessette, who had lunch with the couple on July 14, 1999, agreed with her brother-in-law that Carolyn would have fun.

John promised he’d never make her go to another big Kennedy compound to-do after this one. Lauren, 34, an investment banker at Morgan Stanley, was going to fly with them, too; they’d drop her off at the airport on Martha’s Vineyard and hop on over to Hyannis Port.

And yet also on July 14, Richard Bradley remembered to Vanity Fair that he overheard John screaming at Carolyn on the phone through his office door. 

“In startling, staccato bursts of rage, John was yelling,” Bradley said. “His yells would be followed by silences, then John’s fury would resume. At first I could not make out the words. Then after a particularly long pause, I heard John shout, ‘Well, goddamnit, Carolyn. You’re the reason I was up at three o’clock last night!’ The shouting lasted maybe five minutes, but John’s office door stayed shut for some time.”

That night at the Stanhope, as reported by Edward Klein in his 2003 book The Kennedy Curse: Why Tragedy Has Haunted America’s First Family for 150 Years, John told a friend over the phone, “‘I want to have kids, but whenever I raise the subject with Carolyn, she turns away and refuses to have sex with me.'”

“‘It’s not just about sex,'” he added. “‘It’s impossible to talk to Carolyn about anything. We’ve become like total strangers.'”

Then, John’s friend told Klein, he exclaimed, “‘I’ve had it with her! It’s got to stop. Otherwise we’re headed for divorce.'”

As it turned out, he and Carolyn were on the same page about something having to give, or else—albeit for different reasons.

St. Martin’s Press

“She told me she felt manipulated and compromised, as if she had no authority over her own life,” Carolyn’s friend told Taraborrelli. “She said she was putting John on probation. ‘I’m going to give it three more months and see how I feel,’ she said.” Carolyn admitted she might be over-dramatizing the situation, but she said she needed “a cooling-off period and that in a few months she’d have more clarity. They’d been having a lot of marital problems lately, she said, and she was worn down by then.”

But, the friend was admittedly wondering at the time, “Who divorces John Kennedy Jr.? You’d have to be insane, or at least that’s what people will think.”

The couple had started marriage counseling that March. “It’s all falling apart,” John lamented to another friend from his perch at the Stanhope.

And he didn’t just mean his marriage. George was in serious financial trouble, the publishing business being notoriously difficult even then, before the death knell of print had sounded, and John went to meet potential investors in Toronto in early July. He flew himself up there, with a copilot.

But even if he lost his magazine, he was determined not to lose Carolyn, and he was looking forward to putting that plan into action somehow during Rory’s wedding weekend.

Inside JFK Jr. and Carolyn-Bessette Kennedy’s Last Hours

July 16, 1999, a Friday, started off normally for John. He went to work, had lunch with a group of George editors and attended an afternoon staff meeting, after which John “was in really great spirits,” a staffer later told the Washington Post.

Lauren met John at the George office after work and they drove together to Essex County Airport in New Jersey, where John kept his single-engine Piper Saratoga. It took awhile in traffic and they arrived closer to 8 p.m. Carolyn took a car service to meet them.

One of John’s instructors was scheduled to accompany them on the short trip to Cape Cod, but he had to cancel. John, who had had his pilot’s license for a little more than a year but had yet to get his instrument rating, didn’t arrange for anyone to take his place.

The sun was beginning to set as the 38-year-old went through his pre-flight preparations. Kyle Bailey, an experienced pilot who had also been planning to fly to Martha’s Vineyard that night, recalled the haze he saw instead of the five to 10 miles of visibility reported by the Federal Aviation Administration. “It was already getting dark and the wind was picking up,” Bailey told Christopher Andersen. “So I decided it wasn’t worth the risk.”

The Kennedys were cleared for takeoff at 8:38 p.m.

At 9:26 p.m., they passed Westerly, R.I., at 5,600 feet and headed out over the Atlantic, toward Martha’s Vineyard. John hadn’t filed a flight plan with the FAA because he was flying under visual flight rules, as opposed to using instruments—which is what pilots use when visibility is bad. 

When you can’t see any lights below, which the conditions that night would have prevented John from doing, “you are totally, completely in the dark—literally as well as figuratively—if you don’t know how to rely on your instruments,” Tom Freeman, a local pilot, told Andersen. “It’s a sickening, scary feeling.”

At 10:05 p.m., air traffic control on Martha’s Vineyard radioed that the Piper Saratoga hadn’t arrived.

Providencia Paredes had been waiting for John and Carolyn at their house on the Vineyard, to get them settled. 

In diary entries reported on by the New York Post in 2013, Robert F. Kennedy Jr. remembered going with his then-wife Mary to his cousin’s home several times, only to find out that they still hadn’t arrived. By 3 a.m. on July 17 they got the news that John’s plane was officially missing. “The water was 68 degrees so some people had hope they might still be alive but I had none,” Robert Jr. wrote.

On July 18, Coast Guard officials said for the first time that the missing parties were likely dead, and Navy divers recovered the bodies of JFK Jr. and the Bessette sisters, still strapped into their seats, from the Atlantic on July 21. It was determined that they had all died instantly. The plane’s splash point was figured to be just off the western tip of Martha’s Vineyard, near a private beach that Jackie had left to Caroline and John. 

Though there was dissension within the Kennedy family how best to honor John and his wife in the wake of the latest sick twist of fate to befall their storied dynasty, ultimately he and Carolyn and Lauren were cremated. Their ashes were placed in Tiffany-blue boxes and scattered off the coast of the Vineyard on July 22.

Richard Corkery/NY Daily News Archive via Getty Images

“Had he not crashed the plane, it would have been a meaningless few weeks of tension,” a close friend of John’s told People in 2017 about John and Carolyn’s much-dissected and now legendary marital troubles, “but it took on a life of its own because it was the last chapter of their life. One week they could have been at war, and the next week they could be right back in love—we’ll never know.”

Ted Kennedy delivered the eulogy for his nephew at a memorial service held on July 23 at the Church of St. Thomas More on New York City’s Upper East Side.

He was a devoted son and brother, “and for a thousand days, he was a husband who adored the wife who became his perfect soul mate,” the senator, who died in 2009, said. “John’s father taught us all to reach for the moon and the stars. John did that in all he did—and he found his shining star when he married Carolyn Bessette.”

“How often our family will think of the two of them, cuddling affectionately on a boat, surrounded by family—aunts, uncles, Caroline and Ed and their children, Rose, Tatiana, and Jack— Kennedy cousins, Radziwill cousins, Shriver cousins, Smith cousins, Lawford cousins—as we sailed Nantucket Sound,” Ted continued. “Then we would come home—and before dinner, on the lawn where his father had played, John would lead a spirited game of touch football. And his beautiful young wife—the new pride of the Kennedys—would cheer for John’s team and delight her nieces and nephews with her somersaults.”

“We loved Carolyn. She and her sister, Lauren, were young, extraordinary women of high accomplishment—and their own limitless possibilities. We mourn their loss and honor their lives. The Bessette and Freeman families will always be part of ours.”

In Teddy’s assessment, Carolyn had always fit right in. That’s certainly how John wanted her to feel. And maybe, if they had been given more time—more than the paltry five years they had together, anyway—a different picture would have eventually emerged.

For more insight into the couple’s last days, read on for the biggest revelations from Elizabeth Beller‘s Once Upon a Time: The Captivating Life of Carolyn Bessette Kennedy:

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The Untold Story

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.

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Carolyn Changes Clothes

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.

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How I Dressed for Your Mother

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.”

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Armed for Battle

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.”

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Carolyn Was Never Left Alone

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.

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Like a “Caged Animal”

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.”

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The Papers of Record

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.

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Off the Clock

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.'”

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At a Loss for What to Do Next

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.”

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A Vicious Cycle

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.

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Never-Ending Bump Watch

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.

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The Doom Loop

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.”

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Hard to Believe

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. 

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The Way They Were

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.

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Carolyn Was Turning a Corner

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.

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The Happy Times

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.

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Love of Her Life

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.”

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The Mob Turns Into Mourners

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.

Photo by Justin Ide

Hindsight Hurts

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.”

(Originally published July 16, 2019, at 3 a.m. PT)

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