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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, 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 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 in 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.
John, who would have turned 60 years old on Nov. 25, met Carolyn in 1994 at a Calvin Klein-hosted event and 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 Paredes 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.,” Terenzio recalled in her 2012 book Fairy Tale Interrupted, “and she intimidated the hell out of me.” When she first met Carolyn, though, Terenzio 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, per Taraborrelli.
“Carolyn was also worried marriage would change everything,” Terenzio 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.
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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 had, ready or not, become 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), says in Taraborrelli’s 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,” Bradley 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. Price 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.”
John himself had said that he didn’t want to be “‘that creepy Kennedy who doesn’t care what his girl thinks about anything. I hate those guys,'” poet and Grateful Dead lyricist John Perry Barlow, a close friend and mentor to John since the 1970s, recalled to Taraborrelli.
So though numerous issues would plague John and Carolyn’s relationship in the months and 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 witnesses recalled that they just 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 told Taraborrelli. “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. 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.”
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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 quipped, deadpan.
“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.”
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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.”
His 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, that is).
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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. I’d rather be a good one,” John, determined to forge his own path, once said.
Again, however, he was still JFK Jr.
So Ethel Kennedy decided to have a chat with Carolyn after that little blowup in the park, and she sent a plane to pick her up and bring the young woman to Hickory Hill, the RFK family estate in Virginia.
Widowed at 40 in 1968 and left to raise 11 children, Ethel sought to infuse her nephew’s insecure girlfriend 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.”
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?”
Though the press would never be any less relentless, JFK Jr. and Carolyn Bessette at least pulled off the wedding of the year without anyone aside from their closest family and friends knowing anything about it (and still, plenty of people left out of the loop).
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.
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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.
On Sept. 23, 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
“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.”
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And so John F. Kennedy Jr. and Carolyn Bessette-Kennedy embarked on their next chapter together as husband and wife.
But the story didn’t change: not their clashing temperaments, not 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. Her driver had been speeding through a tunnel trying to lose the paparazzi on their tail.
“I’m not sure what I’m going to do about Carolyn,” John told his friend Billy Noonan. “She’s really spooked now.”
The 2019 TLC special JFK Jr. and Carolyn’s Wedding: The Lost Tapes features low-grade camcorder footage shot by Noonan, in attendance with his wife Kathleen on that day, and a charming moment where John grabbed Noonan’s camera and started filming.
“What I liked about John and Carolyn is that there were like everybody else in general,” Noonan reminisced on the show. He also noted, “No one ever expected that three years later we’d be in another church for another reason.”
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 toast. “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.”
Also, before they got married, Carolyn had 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. There have been too many deaths in the family already,” Jackie told her only son, according to Christop