JFK Jr. and Carolyn Bessette: A Love Story of Secrets and Secrets

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

Apart from clearly declining, she didn’t show any signs either. However, quite interestingly, the 29-year-old Calvin Klein representative, who had been involved with him for nearly a year following years of ambiguity, wasn’t completely convinced that she was prepared to face the implications of marrying him. In essence, this union would involve a blending of lives accompanied by numerous advantages, but also a significant amount of personal concessions, without even considering the direct threats to her privacy.

Over time, I’ve become more than an acquaintance with the Kennedy clan at their Hyannis Port retreat, and let me tell you, there’s no overstating the aura surrounding this legendary family. They may be as human as any other bloodline, but they have woven themselves into the very tapestry of American culture for much of the 20th century.

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

Carolyn adored John, yet a source of ongoing disagreement in their relationship was her discomfort around his large family on Cape Cod. The organized gatherings during holidays and weekends were overseen by Ethel Kennedy, the widow of Robert F. Kennedy, and the Kennedy brothers, whose sporting activities and social events appeared to be straight out of a Ralph Lauren advertisement.

Or a rowdy fraternity party.

As someone born in White Plains, N.Y., and raised in affluent Greenwich, Connecticut, by my mother and renowned orthopedic surgeon stepfather, I wasn’t exactly a stranger to culture. Yet, I often felt like an outsider. On the shores of Hyannis Port, I observed John Kennedy, not just another cog in the Kennedy machine, but the charming figure he presented in New York City. Despite my independence and self-assuredness, being in their presence made me feel diminished and insecure, a towering 5 feet 10 inches reduced to something less.

John shared with his old friend Gustavo Peredes, who was closely acquainted with Jacqueline Kennedy Onassis’ aide Providencia Paredes and had ties to the young couple, “We aren’t skilled at handling insecurity.” He added, “That’s not something you’d find on the Kennedy list of concerns.

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

Approximately three weeks following the proposal by People’s Sexiest Man Alive in 1988 during the Fourth of July weekend on Martha’s Vineyard, she eventually agreed to his proposal.

According to RoseMarie Terenzio, who served as John’s executive assistant from 1994 onwards, she believes that incident further fueled John’s desire to wed her. (The Kennedy Heirs author J. Randy Taraborrelli was informed of this by RoseMarie.)

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

In 1992, John encountered Carolyn who had been tasked to manage a special-fit session for a well-known brand, Calvin Klein, attended by the former first son. From that moment on, he was captivated by her.

Initially, he often expressed irritation, as attorney Brian Steel, who first crossed paths with John while working at the Manhattan District Attorney’s office, noted in the 2018 ABC News special The Last Days of JFK Jr. “He would complain, ‘She hasn’t returned my call.’ John didn’t take kindly to such situations.

In 2014, Gustavo expressed to others that Carolyn doubted his sincerity. He found it hard to comprehend her rejection as such an occurrence was unprecedented for him.

In her 2012 book, Fairy Tale Interrupted, RoseMarie mentioned that Carolyn was the exact type of girl she envisioned dating someone like John Kennedy Jr., and she found Carolyn intimidating. However, when they first met, RoseMarie noticed that Carolyn was unlike most beautiful women in Manhattan, as she didn’t make an effort to stand out or impress, but rather, she seemed natural and unpretentious.

Carolyn maintained an unaffected demeanor, yet she couldn’t help but notice John’s presence. She found herself repeatedly saying, “Wake up, he’s just a man,” to Carole Radziwill (née DiFalco), who was soon to marry Anthony Radziwill, John’s cousin and closest friend, in August 1994.

In her writing, RoseMarie expressed that Carolyn too shared concerns about how marriage might alter everything, as she knew that the formal commitment would significantly impact both herself and John, particularly since he was quite traditional and his social standing wouldn’t allow him to remain unmarried indefinitely.

In his life, John had always been surrounded by female companionship, having dated notable women such as Daryl Hannah, Sarah Jessica Parker, and Madonna. However, by the mid-’90s, the once-crowned prince of the fallen kingdom of Camelot yearned for a genuine partner to stand by his side.

Anthony’s decision to advance was partially influenced by grief, as his mother, with whom he shared a strong bond, passed away in May 1994. In the summer of 1995, Anthony received devastating news when his previously defeated testicular cancer resurfaced.

Following a year with Carolyn, he was eager to embrace life fully, in various aspects. In September of that year, accompanied by his fiancée, John unveiled his glossy magazine titled George, a venture he imagined would seamlessly blend the spheres of politics and celebrity which were already deeply entwined. The first cover featured none other than Cindy Crawford, portrayed as George Washington and captured by Herb Ritts, for the October/November 1995 issue.

As an ardent admirer, I can’t help but echo Richard Bradley’s sentiments, who, under the pen name Richard Blow at George Magazine, proclaimed in The Kennedy Heirs, “It wasn’t just a triumph for John, but for Carolyn as well.” His excitement was palpable about John, his relentless spirit, ambition, and the discovery of a purpose that ignited him. He yearned to be side by side with him throughout this journey. Richard shared that he believed this was the first of many publications John might orchestrate, and he had an intriguing concept for a men’s style magazine, something akin to Esquire but with a broader mainstream appeal.

Richard added, “It seemed to you when you were with them that John and Carolyn made a strong power couple within their family. They reminded you of pairs like Jack and Jackie, Bobby and Ethel, or Sarge and Eunice Shriver. John admired the Kennedy power couples from the past, and he wanted to emulate this image with himself and Carolyn. So, in essence, Carolyn was taking on the role of the woman behind the man, and John appeared pleased and proud about it. I believe his mother would have felt the same way.

For Carolyn’s peace of mind, it was crucial that John wasn’t excessively traditional. Unlike numerous men in his family, including his deceased father, President John F. Kennedy, he aimed to treat their relationship and future marriage with sincerity.

In a conversation with Stewart Price, as mentioned in “The Kennedy Heirs”, Carolyn confessed, “I find their dynamics quite unsettling.” Later, Stewart tried to reassure her by pointing out John’s uniqueness. To this, Carolyn responded, “It’s beneficial that he’s unique. I know my own self and I’m certainly not the Kennedy wife who’d be stuck at home with the kids while her husband goes astray. No, I’m the fiery Kennedy wife who might end up in trouble for taking charge due to their unruly behavior.

In the 1970s, John Perry Barlow, a renowned poet and lyricist for The Grateful Dead, who was close friends with and mentored John, remembered that the young man expressed disdain towards being seen as “the indifferent Kennedy type who doesn’t value his girlfriend’s opinions. I despise those kinds of men.

What Did Carolyn and JFK Jr. Fight About?

Despite a multitude of problems arising in John and Carolyn’s relationship over the short span of months and years, it is generally agreed that infidelity was not among them. However, as per certain sources, Carolyn would allegedly mention to John during arguments that she was involved with an ex-boyfriend.

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

Historian Steven M. Gillon, a former classmate of John’s at Brown University and later a contributor to “George”, stated in 2019 to InStyle that among all the people John had been with, Carolyn was the one who would challenge him, confront him, and he believes that to some degree, John required this kind of stance.

Despite the glowing portrayals of John as a charismatic and promising politician, he was also known for his strong-willed nature and quick temper, which were not often discussed. However, those who had previously dated him were well aware of this side of his personality.

1996 was a year I’ll never forget! As an ardent fan, seeing my beloved couple, him and Carolyn, caught in a heated dispute in Washington Square Park on February 25th was like a punch to the gut. We were all strolling around with our dogs, mine being Friday, when it seemed like the world came crashing down. Onlookers reported that they started shouting at each other – a sight I would’ve given anything to avoid! That day, Washington Square Park wasn’t just a park; it was a battleground of emotions.

In a different phrasing: She pushed him, and John seized her wrist, attempting to remove Carolyn’s engagement ring from her finger. At that moment, she was holding Friday’s leash. According to several accounts—including the New York Daily News summary titled “Sunday in the Park With the George Editor”—he shouted, “The ring is yours, but you won’t have my dog!

John took a seat on the sidewalk, looking troubled, and Carolyn joined him there, offering comfort. Later, they departed from the park, holding hands.

Speaking about George, Richard Bradley remembered that the fight was disastrous for public relations. Our main concern was how it might influence advertisers, particularly those in women’s fashion and cosmetics. I believe John felt remorseful, but unfortunately, it was Carolyn who bore the brunt of negative public opinion. In the video, she appeared as the aggressor, which solidified an unfavorable image of her as emotional and dissatisfied. We were all aware that John had a temper, but the public remained unaware.

In essence, he went on to say that it seemed as though Carolyn had a negative influence on America’s prince, transforming him, and many people blamed her for this. He also suggested that, ultimately, Carolyn was more upset with herself for allowing John to embarrass her in public than she was about the actual argument they had.

Isn’t it often the case that things turn out this way? To many who were still mourning the loss of JFK Jr., Carolyn was both a hero and a villain – the woman who captured the prince’s heart, yet brought him grief. And with all the turmoil this family has faced already, couldn’t they have been spared this additional pain?

Regardless of the constant hassle from paparazzi who camped outside Carolyn’s building and resorted to provocative behavior to provoke her, John advised her to stay calm and disregard them. Being accustomed to autograph hunters and camera flashes himself, having dealt with it daily for years, he found this kind of attention par for the course.

Friends of the pair urged Carolyn to avoid interacting with the media – don’t let their name-calling bother you, as you can’t prevail in any case, they suggested – and equally recommended John to be more considerate towards Carolyn’s apprehensions. In essence, she didn’t have a background accustomed to that lifestyle.

As a die-hard fan, I couldn’t help but feel a knot in my stomach when the gossip that John allegedly struck Carolyn in the park started to spread like an inferno. It wasn’t long before it became the hot topic of conversation, even making its way into 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.

In his 2002 best-seller, American Son: A Portrait of John F. Kennedy Jr, Bradley remembered that he was aware John had a hot temper and Carolyn wasn’t shy or timid. However, the intensity of their anger (as shown in the video) stood out sharply against the affectionate moments I had witnessed between them.

Ariel Paredes, Gustavo’s daughter and a close friend of Carolyn’s, recounted to People in 2014 that they were passionate. She said, “They loved intensely and they argued fiercely, but they were undeniably a couple.

In my perspective as a lifestyle expert, I’d rephrase Gillon’s statement in 2019’s book “America’s Reluctant Prince: The Life of John F. Kennedy Jr.” as follows:

“The underlying reason for the infamous spat, and subsequent disagreements, was Carolyn’s persistent concern that John allowed others to trample upon him without resistance.

In Carolyn’s opinion, John tended to be overly compliant when people requested favors. Moreover, as Gillon mentioned, she was still upset about a recent wedding they attended for acquaintances, where it seemed clear to her that the groom had manipulated their way into getting coverage on the New York Times society page by asking John to be his best man.

Gillon added, “Whether she was correct or not, she was extremely angry with John for not speaking up by leaving. This was an old argument they’d had many times privately, but on this occasion, it spilled over into the public arena.

Meanwhile, John’s sibling, Caroline Kennedy Schlossberg, is among those family members who considered the park fight a concerning development. In fact, Caroline, who wasn’t particularly fond of John’s future wife to begin with, believed, as per Taraborrelli, that his future wife should have been aware to steer clear of public situations that might provoke such reactions.

In a previous account, Senator Edward Kennedy served as a guiding figure for John following a particular incident. However, John reportedly found it difficult to engage due to his shock and embarrassment. This event tarnished not only John’s reputation but also the Kennedy family’s image. Additionally, Ted Kennedy was aware that John aspired to be viewed as a serious businessman alongside George. Unfortunately, this occurrence contradicted the professional image John wished to present.

While John still considered a potential future in politics, George was a project that John was deeply committed to, intending to achieve it independently alongside his business partner, Michael Berman.

However, much like it’s often said by Kennedys throughout history, no individual born into this family, particularly the males, is immune to the heavy burden of expectations and historical legacy that inevitably presses down on them.

In response to others constantly saying he could become an exceptional person, John assertively stated, “I prefer to be a decent individual instead.

Again, however, he was still JFK Jr.

After their disagreement in the park, Ethel elected to talk things over with Carolyn, so she arranged for an aircraft to transport her future niece-in-law from wherever she was and bring her to Hickory Hill, the Kennedy family home in Virginia.

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

At age 40 in 1968, Ethel was left a widow and tasked with raising 11 children. This remarkable woman, who passed away at 96 in October 2024, attempted to instill some of her resilience, earned through tough times, into her nephew’s hesitant companion. She undeniably knew the sensation of living in the wake of a dominant male figure’s influence.

Ethel mentioned that she had a similar experience with Bobby initially, as relayed by the friend Carolyn introduced to Hickory Hill that day for support. This individual later told Taraborrelli the story. After some time, Ethel realized that in order to thrive within the Kennedy family, one must look at themselves in the mirror every morning and affirm, “I am enough.” In essence, she found solace in this simple truth: ‘I am enough.’ Over time, it became clear that this sentiment resonated deeply, helping her understand that she possesses inherent worth, a reality no one, not even the Kennedys, could ever take away from her.

Additionally, as this witness testified, Ethel advised Carolyn similarly to what she had told her own daughters and daughters-in-law: “Stand by your husbands, but don’t let them persuade you into wrongdoing. They might tempt you, and they often do. I’ve noticed it for a long time. However, you must resist the temptation. You need to be stronger than that.

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

Ethel insisted, “In public places, please,” implying that the men involved were quick-tempered and might provoke inappropriate behavior from you in full view of everyone. She also advised Carolyn, “I believe you possess more influence than any other woman John has dated. Why? Because you’re intelligent, and because you have compassion. So, don’t let John, journalists, photographers, or anyone else alter your essence.” She tapped Carolyn on the chest to emphasize her point. “Got it?

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

Despite the media’s persistent scrutiny, JFK Jr. and Carolyn Bessette managed to execute a secretive yet remarkable wedding, with only their immediate relatives privy to the details.

On September 21, 1996, the couple exchanged their vows at the First African Baptist Church located on Cumberland Island, accessible only via ferry, personal watercraft, or helicopter, off the coast of Georgia.

The Kennedys reserved every room at the solitary Greyfield Inn, which is the only hotel on the island, and leased several private homes as well. Later on, Carolyn secretly produced the wedding programs in the George office during off-hours. RoseMarie played a significant role in organizing everything, even creating a phony itinerary that made it seem like John and Carolyn would be in Ireland over the weekend. A week prior to the event, John himself extended invitations to everyone for a gathering.

Upon my friends departing towards the church, I caught sight of a helicopter in the distance. However, it merely hovered above us for a moment before disappearing from our view.

Carolyn donned a striking Narciso Rodriguez crepe silk slip dress and Manolo Blahnik heels, while John opted for a dark blue suit and his father’s timepiece. Caroline acted as Carolyn’s matron of honor (at John’s request), with daughters Rose and Tatiana serving as flower girls, and son Jack taking on the role of ringbearer. Anthony Radziwill stood alongside John as best man, and Sen. Ted Kennedy, along with John Perry Barlow, were among the 50 special guests invited to attend.

Instead of enlisting a well-known Kennedy wedding photographer named Denis Reggie to document their special day, they selected him for this crucial task. It was Denis Reggie who took the photograph of John tenderly kissing the bride’s hand as they exited the church, an image later shared with the media.

Reggie recalled in 2021 telling TODAY that they managed to create an understated yet beautiful and memorable weekend without making it overly grand. He also expressed his admiration for the moment he captured, stating that it held a magical quality. Looking at Carolyn’s face, he could see surprise, joy, love, romance, and many other wonderful emotions.

On September 23, 1996, a memo was distributed to the staff at ‘George’ magazine, as recounted by the publication’s creative director, Matt Berman, in his 2014 book titled “JFK Jr., George, & Me.

“To: All the Gentlewomen and Gentlemen of George

“From: John

“Re: Breaking News

I felt it was important to share with everyone: While you were all diligently working, I took the opportunity to get married secretly, as I’m sure you can understand why discretion was necessary in this case.

As a devoted admirer, I can’t help but share my excitement as John F. Kennedy Jr. and his beloved wife, Carolyn Bessette-Kennedy, began their new journey as a married couple, setting sail into the next beautiful chapter of their lives together.

However, formalizing their relationship didn’t alleviate their contrasting personalities, persistent communication problems, or the media’s relentless fascination with their lives. The paparazzi continued to pursue them, hoping for a sequel to their public display in the park back in February 1996.

In July 1997, Carolyn traveled to Milan for Gianni Versace’s funeral, who was tragically murdered outside his Miami Beach mansion. Seated directly in front of her was Princess Diana, a woman John once shared tea with at the Four Seasons in New York City. Despite turning down an appearance on the cover of George magazine, Princess Diana captivated John.

Five weeks following our brief encounter with Diana, Princess of Wales, I was deeply saddened by the tragic news of her demise in a car accident in Paris, alongside her companion Dodi Fayed. The driver, apparently trying to evade pursuing photographers, tragically lost control and collided with a pillar in a tunnel.

John shared with his buddy Billy Noonan that he’s unsure of how to handle Carolyn because she’s become quite frightened lately.

In the book “America’s Reluctant Prince”, it is mentioned that Carolyn’s mother, Ann Freeman, expressed doubts about John being the suitable partner for her daughter, as she voiced this concern during her wedding toast.

As a lifestyle expert, let me rephrase it for you: Anthony eased the awkwardness with his best man speech by saying, “We’re all here because we know why John would marry Carolyn. She’s smart, beautiful, and charismatic… But what I can’t help but wonder is, what does she see in John? Over the years, he’s delighted in teasing me, playing pranks, and generally giving me a hard time. However, it seems that some of the qualities that may have drawn Carolyn to John are his compassion, his charm, and his golden heart.

Carolyn found herself growing closer to George, which caused some tension for John’s partner, Michael Berman. As a result, Michael decided to sell his share of the magazine in 1997. Coincidentally, Carolyn yearned for her own professional path but was uncertain about what she could pursue or was capable of, given her high-profile status.

In the year 1998, the daring explorer John, who had a penchant for speed, height, and seclusion, decided to learn how to fly – an activity that his late mother had earnestly advised against.

Jackie implored her sole child not to proceed with whatever he was planning, as detailed by Christopher Andersen in his book, “The Good Son: JFK Jr. and the Mother He Loved“. She expressed concern, stating that there had been enough sorrow and loss within their family.

Two of President Kennedy’s elder siblings, Joseph Jr. and Kathleen (nicknamed “Kick”), met untimely deaths in air accidents during the 1940s. Ethel Kennedy experienced the loss of both her parents in an aircraft accident in 1955, followed by the demise of one of her brothers 11 years later. Ted Kennedy survived a crash that claimed two lives in 1964 but was gravely injured. Jackie’s stepson, Alexander Onassis, perished in a plane crash soon after takeoff in 1974. As recounted by Jackie’s partner for the final 14 years of her life, Maurice Tempelsman, she had an eerie feeling that John would meet his end while piloting a plane.

As it became clear, Carolyn wasn’t actually in favor of John pursuing a pilot career, and she never took flights with him (neither Tempelsman nor Ted Kennedy did this either) without an instructor present. She was well aware of his tendency to be forgetful—he often misplaced his wallet or keys, she claimed—and she had concerns about his focus. One day at a café in Martha’s Vineyard airport, she openly expressed her lack of trust in him to a waitress, as reported by Andersen.

Back in May 1999, John had an accident while flying a small aircraft that resembles a glider, but it also has a propeller – a type known as an ultralight powered parachute. Unfortunately, during the flight, he sustained an injury to his right ankle.

Six weeks on, he was still using crutches and hopping around, but the excitement to pilot a plane to attend his cousin’s wedding at Hyannis Port – that was Rory Kennedy – was palpable. And yes, with an instructor by his side for safety.

Carolyn had no interest in attending. Her disinterest in spending time with John’s family, which had persisted throughout their relationship, was one of the many constants, and she wasn’t particularly fond of Rory, Bobby Kennedy’s youngest child, who was conceived when Ethel was pregnant during the time when her husband was assassinated.

According to one of Carolyn’s friends, they had a significant disagreement regarding the matter. For Carolyn, it wasn’t just about winning the argument; it was about respect, visibility in her marriage, and being acknowledged within the family. Being surrounded by many strong personalities among the Kennedys, Carolyn discovered that she needed to assert herself if she ever wanted to make her voice heard.

In my role as a lifestyle expert, allow me to share an intriguing tale from July 12, 1999. On that day, I found myself checking into the elegant Stanhope Hotel on Fifth Avenue. Meanwhile, my trusted confidant was nestled comfortably in one of their loft’s inviting guest rooms.

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

RoseMarie was concerned about the impression of Carolyn’s absence at the wedding causing more problems in their relationship. She asked John directly to make sure Carolyn attended. In her book, she expressed her frustration by telling her boss’ wife bluntly, “Carolyn, this just doesn’t make sense! You’re too smart for this. You don’t want to put John in an awkward situation explaining where you are, and you certainly don’t want to be judged yourself. You already face enough of that.

As a fervent admirer looking back, it was none other than my sister-in-law, the remarkable Lauren Bessette, who dined with RoseMarie and Carolyn on the 14th of July, 1999. She concurred with her brother-in-law that the joyful Carolyn would undoubtedly relish the experience.

John assured that he wouldn’t take her to another Kennedy family gathering of such magnitude following this one. Lauren, aged 34 and an investment banker at Morgan Stanley, was also planning to travel with them; they would be dropping her off at the Martha’s Vineyard airport before proceeding to Hyannis Port instead.

On the same day, July 14th, Richard Bradley recalled to Vanity Fair that he had heard John shouting at Carolyn on the phone from his office.

According to Bradley, John’s outbursts of anger were sudden and brief, punctuated by moments of silence. Initially, I couldn’t understand what he was saying. However, after a prolonged pause, I heard him exclaim, “Well, damn it, Carolyn! You’re the one who kept me awake at three in the morning!” This shouting went on for about five minutes, but his office door remained closed for a longer period.

According to Edward Klein’s account in his 2003 book “The Kennedy Curse: Why Tragedy Has Haunted America’s First Family for 150 Years,” John expressed to a friend over the phone that he desired children, but whenever he brought up the topic with Carolyn, she would shy away and reject his advances.

He continued, “It’s not solely about intimacy, it’s more like we can’t have a conversation with Carolyn at all. We might as well be complete strangers.

Later on, John’s friend conveyed to Klein that he declared emphatically, “I can’t take it anymore! This needs to end or else we might be facing a divorce.

In the end, they both agreed that something needed to change, albeit for separate motivations.

According to Taraborrelli, Carolyn’s friend expressed that Carolyn felt controlled and powerless, as though her life wasn’t hers to manage independently. She stated that she was placing John under observation for a while longer, adding, “I’ll check in with myself in three months and see how I feel.” However, Carolyn acknowledged that she might be exaggerating the situation, yet she emphasized the need for some distance to gain perspective. She explained they had been experiencing marital difficulties and her spirit was exhausted by then.

However, it’s worth noting that his friend was contemplating aloud, “Who could possibly divorce John F. Kennedy Jr.? Such a person must either be quite mad, or so others might assume.

They began marriage therapy in March, as John put it sadly to a friend while they were both at the Stanhope.

Apart from his marriage, George was facing some severe financial struggles. The publishing industry was already tough at that time, long before the demise of printed media became apparent, and John decided to seek out potential investors in Toronto during early July. He made the journey himself, accompanied by a copilot on a plane.

However, though he might have misplaced his magazine, he was resolute about not letting go of Carolyn, and he eagerly anticipated finding a way to execute his plan during Rory’s wedding weekend.

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

1999-07-16, a Friday, began routinely for John. He headed to work, shared lunch with some of George’s editors, and participated in an afternoon team gathering. Later, as reported by the Washington Post, John was found to be in high spirits following this meeting.

After wrapping up work, Lauren encountered John at the office of George, and they journeyed together to Essex County Airport in New Jersey, which happened to be where John parked his single-engine Piper Saratoga. The trip was prolonged due to traffic, and they finally arrived around 8 p.m. Carolyn arranged for a ride service to join them.

Originally, one of John’s teachers was supposed to join them on their quick trip to Cape Cod, but he unfortunately couldn’t make it. Since John had only recently obtained his pilot’s license over a year ago and hadn’t yet earned his instrument rating, he didn’t arrange for someone else to take the teacher’s place.

As the sun dipped below the horizon, a seasoned pilot named Kyle Bailey, who had intended to fly to Martha’s Vineyard that evening, remembered the foggy conditions he observed rather than the clear visibility of up to 10 miles as reported by the Federal Aviation Administration. “The darkness was setting in and the wind was growing stronger,” Bailey explained to Christopher Andersen. “I determined it wasn’t safe enough for the flight.

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

At 9:26 PM, they flew past Westerly, Rhode Island, at an altitude of 5,600 feet and began their journey over the Atlantic, bound for Martha’s Vineyard. John didn’t submit a flight plan to the Federal Aviation Administration because he was adhering to visual flight regulations instead of relying on instruments – a method pilots use when visibility is poor.

In pitch-black conditions where no navigation lights could be spotted, as a seasoned aviator like Tom Freeman puts it, “you’re plunged into an absolute, unadulterated darkness—both physically and metaphorically—if you’re not adept at relying on your equipment.” It’s a chilling, disquieting sensation.

10:05 PM, the air traffic controllers at Martha’s Vineyard reported over the radio that the Piper Saratoga had failed to make its expected arrival.

Providencia Paredes was there to welcome John and Carolyn at their vacation home on the Vineyard, helping them feel comfortable and settled.

2013 diary entries mentioned in the New York Post revealed that Robert F. Kennedy Jr., along with his wife Mary, frequently visited his cousin’s home, only to discover they hadn’t arrived yet. However, by 3 a.m. on July 17, they received word that John’s plane was missing. “Since the water temperature was 68 degrees, some people held out hope that they might still be alive, but I had no such optimism,” Kennedy Jr. wrote in his diary.

On July 18, Coast Guard officials expressed for the first time their belief that those who were missing were unfortunately deceased. Navy divers subsequently found the bodies of JFK Jr., along with the Bessette sisters, in the Atlantic Ocean on July 21. All three were discovered still buckled into their seats. The conclusion was reached that they had all perished instantly. It was estimated that the plane’s impact site was near a private beach on Martha’s Vineyard, which Jackie had previously passed on to Caroline and John.

Despite disagreements among the Kennedy family about how to commemorate John and his wife following the tragic turn of events that hit their renowned lineage, they were eventually cremated. Their ashes were stored in Tiffany-blue containers and dispersed off the coast of the Vineyard on July 22nd.

If John hadn’t crashed the plane, his turbulent relationship with Carolyn would have been an unimportant period of stress for a few weeks,” said one of John’s friends to People magazine in 2017. “However, it became significant because it was the final part of their lives. One week they might have been at odds, and the next they could be back in love—we’ll never truly know.

On July 23, Ted Kennedy gave a heartfelt tribute at a memorial service held at the Church of St. Thomas More located in New York City’s Upper East Side, honoring his nephew.

For a thousand days, he was an ardent husband to the woman who turned out to be his ideal soul mate, the senator remarked before his passing in 2009. John’s father had inspired us all to aim for greatness among the heavens, and John embodied this spirit in every aspect of his life—finding his radiant star when he wed Carolyn Bessette.

Ted reflected on how frequently we’d remember the two of them, nestled in warmth aboard a boat, encompassed by family – aunts, uncles, Caroline, Ed, and their kids Rose, Tatiana, and Jack, Kennedy, Radziwill, Shriver, Smith, Lawford cousins – as we navigated Nantucket Sound. Later, returning home, before dinner on the lawn where his father used to play, John would initiate an energetic game of touch football. And his stunning new wife, the latest source of pride for the Kennedys, would encourage John’s team and entertain her nieces, nephews, and perhaps even herself with her acrobatic somersaults.

Our hearts deeply cherished Carolyn, along with her sister, Lauren. They were remarkable young women of great achievement, brimming with unbounded potential. We grieve their absence and celebrate their lives. The Bessette and Freeman families will forever remain a significant part of ours.

According to Teddy, Carolyn seemed perfectly at ease wherever she was, which was exactly what John aimed for. If they’d had longer – say, beyond their brief five-year stint – a potentially different image of her might have surfaced over time.

As a devoted admirer, I highly recommend delving deeper into the final chapters of a renowned couple’s life by checking out the most intriguing disclosures from Elizabeth Beller’s book, “Once Upon a Time: The Enchanting Life of Carolyn Bessette Kennedy”.

During her lifetime, Carolyn Bessette stood out as a fashion trendsetter. From her casual yet stylish downtown attire – long skirts paired with fitted white t-shirts and Chuck Taylors that caught everyone’s attention during her time in sales and PR at Calvin Klein, to her elegant Narciso Rodriguez silk crepe wedding dress, and the series of chic monochromatic outfits she wore for events after becoming a society figure alongside John F. Kennedy Jr., her fashion choices were always impeccable.

Since her tragic death in a plane crash alongside her husband and sister Lauren Bessette on July 16, 1999, the admiration for her has transformed into reverence.

In my expert opinion as a lifestyle enthusiast, stepping into the Kennedy circle didn’t merely enhance her inherent style; it was more like a transformation, as suggested in Elizabeth Beller’s 2024 book “Once Upon a Time”.

Instead, Carolyn adjusted her behavior to align with what she believed Jacqueline Kennedy, John’s late mother, would have preferred for her sole child.

In the heat of a passionate summer fling in 1992, John abruptly ended things following a friend’s letter revealing concerns about Carolyn being trouble. For over a year, he found it difficult to reach out and apologize, with Carolyn even changing her phone number to evade him.

During that period, John was connected, albeit intermittently, with his girlfriend Daryl Hannah. However, he never presented Carolyn to his cherished mother before she passed away due to non-Hodgkin’s lymphoma on May 19, 1994. This was one of his significant regrets and a factor that led Carolyn to end their relationship multiple times.

Jackie became closely associated with sophistication and refinement in the eyes of the world. In February 1996, Carolyn transformed her light brunette hair into the iconic cornflower blonde shade, thanks to colorist Brad Johns. She also began shaping her eyebrows extremely thinly and shed some weight from her already slender 5-foot-10 figure.

According to MJ Bettenhausen, the person who everyone knew as Carolyn wasn’t entirely genuine. However, it was believed that she would have eventually found her place. Despite being physically fit and attractive, she became distressingly thin and pale, leading MJ to speculate that she felt pressured to conform to what she thought a Kennedy should be.

1997 marked a pivotal moment for me, as I found myself inexorably drawn to the enigmatic allure of designer Yohji Yamamoto’s creations. Every time I saw Carolyn adorned in his designs, she exuded an air of effortless elegance that was nothing short of captivating. The muted tones and streamlined structures of his clothing, as he eloquently put it in the 1989 documentary “Notebook on Cities and Clothes,” served a dual purpose: they guarded the garments from the whims of fashion, and shielded the wearer’s form from unwanted scrutiny. Perhaps this was Carolyn’s subtle way of blending into the crowd while maintaining her unique style.

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

According to Michelle Kessler, Carolyn would have found it amusing to be referred to as a fashion icon. The truth is, Carolyn wasn’t aiming for that title at all. Instead, she just wanted to live an intriguing life and carry on with her daily activities without any unwarranted attention or disturbances.

Even before John’s passing, it was no secret where John and Carolyn lived. Since their first meeting in 1992, Carolyn had relocated several times: from the East Village when she initially moved to New York from Greenwich, Conn., in 1989; to Greenwich Village in 1993 due to paparazzi camping outside her apartment; and then again to a new West Village residence in 1994 after they managed to find her once more.

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

Despite John and numerous others promising her that the paparazzi would ease off once they tied the knot, photographers continued to wait for her each morning outside. It seems that, according to various reports, the media coverage of their relationship – which had been intense and invasive beforehand – only intensified further.

From my perspective as a lifestyle advisor, I’ve always seen John as a public figure who generously gave back to his community, whether it was by rollerblading or cycling around town, or by sharing romantic connections with renowned personalities such as Daryl and Madonna. He seemed to embrace the limelight that came his way. Yet, when he requested some privacy for his girlfriend, later wife, amidst certain instances displaying intense emotion, it was Carolyn who found herself unfairly blamed for a perceived decrease in John’s patience with the media.

According to Beller, it seems the media failed to realize that John’s defensiveness stemmed from his deep affection for Carolyn, who was clearly upset, prompting him to shield her.

As a lifestyle expert, I’d put it this way: Contrary to the vibrant and outgoing person she truly is, Carolyn has always been uncomfortable in front of the camera, even during her teenage years. Over time, this discomfort seems to have led her towards a more solitary existence.

In the book, her friends portray her as someone who disliked solitude and was constantly active during her single years. She was depicted as an incredibly compassionate friend, one who would rush to the hospital if anyone fell ill or call because she had noticed a particular expression on a coworker’s face earlier in the day and correctly guessed that they needed someone to confide in.

Michelle was often referred to as a “deeply empathetic” friend by those who knew her. However, on one occasion, when she required a confidence boost, she briefly entertained the idea of flirting with another colleague’s boyfriend from out of town, as shared by an anonymous confidant. Yet, it seemed that Michelle regretted this action so deeply that she made a conscious effort to avoid repeating such behavior in the future.

Due to the persistent paparazzi who stood to earn substantial sums, often in five figures, from a single photo, and with her expressions becoming increasingly sad or angry boosting their profits, numerous individuals likened those times to a challenging ordeal for her.

In simpler terms, MJ stated that Carolyn seemed as if she was confined or restricted, similar to a caged animal. Furthermore, Chris Oberbeck, John’s friend and ex-roommate from Brown University, informed Beller that as Carolyn withdrew, the media became increasingly hostile. This made Carolyn appear like a tiger in its cage – pacing back and forth and displaying understandable anger due to her confinement.

According to Beller, not just the tabloids, but even mainstream newspapers such as the Washington Post, New York Times, Detroit Free Press, and Spokane, Washington’s Spokesman-Review often portrayed Carolyn as if she were frivolous and lacking in substance. Her career in fashion was sometimes perceived as being a bit scandalous for someone with John’s noble background.

On October 6, 1996, an opinion piece in the New York Times questioned whether she would have passed not only Jackie’s standards, but also those of Joe Kennedy, the family patriarch who was known not just for his political power, but also the scandals that surrounded the Kennedy family.

The conclusion of the argument was that Carolyn was an ideal fit for “an agreeable young gentleman with promotional skills,” implying that she herself embodied such qualities. However, by collectively supporting this choice, everyone contributed to a subtle form of cultural decline.

For nearly a decade since leaving high school, Carolyn had been employed in various roles, and then, within just three years, she advanced from a VIP sales position at Calvin Klein’s Saks Fifth Avenue boutique to assuming the role of PR Director for the Calvin Klein Collection in 1992.

However, following a public argument with John in Washington Square Park, which was broadcast on television news each evening and later featured as an 11-page article in the National Enquirer, she chose to leave Calvin Klein in March 1996 after seven years.

Instead of potentially causing a diversion for the brand, Beller explains that it was growing difficult for her to enter the office because of the persistent paparazzi.

Previously with the “Improper Bostonian” newspaper, journalist Jonathan Soroff shared with Beller that he met Carolyn at an occasion and she expressed her wish to work but was unable to do so anymore, as she described her life as having turned into a “spectacle.

Carolyn functioned as one of John’s unofficial advisors during the preparation for the launch of his magazine, George. However, she chose to keep a distance from the Sept. 7, 1995, launch to ensure that the spotlight was solely on him and not shared with her or themselves. In other words, she wanted the event to be his special moment, rather than theirs.

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

According to several friends, including Carole Radziwill, she pondered over what her next calling might be if only granted the time. Notably, Carole is 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 passing from cancer in August 1999. In an unusual turn of events, John had been penning Anthony’s obituary before he himself passed away, but it was Anthony who read Psalm 23 at John and Carolyn’s funeral instead.

In Beller’s book, it is mentioned that Carole, who was employed by ABC News at the time, reminisced about a conversation with Carolyn regarding documentary filmmaking in the spring of 1999. She felt this could be a promising path for her friend. The former star of “The Real Housewives of New York City” added that Carolyn also showed interest in returning to school to focus on psychology, leveraging her natural ability to identify the core of someone’s problems and uplifting them.

For much of her public life alongside John, Carolyn openly displayed her disdain towards the media. Like Princess Diana who was also pursued relentlessly, she often looked down as she entered events and refused to put on a forced smile. Additionally, contrary to advice given by John and others, she chose not to placate the paparazzi by posing for a favorable photograph to make them leave her alone.

As she continued to resist, the photographers grew increasingly persistent, moving closer to her until they were almost touching her. Some of them even shouted offensive remarks in an attempt to provoke a response, which only served to further reinforce the perception that she was unapproachable or unfriendly.

Throughout her final 34 months of life, from March 1996 onwards, Carolyn was persistently under scrutiny due to pregnancy rumors, with these suspicions dominating much of the latter part of her marriage.

Carolyn Kennedy – Bassinet, as reported, greeted the public upon their return from Italy with John, where they had to change hotels to avoid photographers, back in June of 1997.

Friends presented Carolyn to Beller as an exceptional caregiver for babies, with a deep affection for children. She earned her education degree from Boston University and even contemplated becoming a preschool teacher at one point. However, according to her statement in Women’s Wear Daily in 1992, she found teaching too conventional for her taste.

Over time, tabloids often blamed Carolyn for not having children, but she openly expressed fear about introducing a child into such a public life where she couldn’t even walk down the street without being pursued by cameras. On the other hand, John prioritized work over family, regularly working late at George and frequently traveling to meet with investors and advertisers.

However, friends informed Beller that during the final months of their lives, John and Carolyn had been actively trying to reconcile their marriage and often discussed starting a family together.

During the autumn and winter of 1997, John and Carolyn experienced a very turbulent period, as Beller observes, due to the media’s persistent coverage of their frequent arguments and impending separation.

Over time, whispers about marital strife led to genuine marital issues. By early 1998, as Beller puts it, Carolyn was on the verge of collapse, and according to John’s long-term friend Jack Merrill, she was in the throes of multiple crises.

Carole explained that Carolyn’s situation was similar to being “manipulated or misled,” and this frequent questioning by others about information they’ve read about you significantly disrupts the course of your relationships. You may end up feeling just as bewildered as the gossip magazines themselves.

The friends Carole, MJ, Michelle, Hamilton South, and Betsy Reisinger Siegel all dismissed the ongoing gossip back then about Carolyn being involved in a relationship with her former flame.

Michelle assured Beller that she “was far too prudent to risk her marriage with an affair,” and Carole and Hamilton merely chuckled at this statement, as per the account of the author.

In the book, various individuals pointed out that while Carolyn often enjoyed socializing, they never witnessed her consuming more than a handful of wine glasses or dirty vodka martinis. Additionally, all these people stated that they had never observed Carolyn using drugs, contradicting rumors from that period suggesting she was heavily into cocaine in 1998.

Among the sad aspects of Carolyn’s tale – encompassing both herself and John – is the fact that all those who knew her, despite her despair over public scrutiny and doubts about the future of their marriage, were convinced that she would ultimately recover…in time.

Initially, it seemed like a minor hiccup – he was constantly busy, and there were trust concerns – but eventually, it became the entire picture. It’s uncertain if their issues would have been too challenging to overcome or if they would have found a way to persevere.

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.

According to William Peter Owen, a friend of the Bessette family, she began to spend increasing amounts of time at her sister Lauren’s apartment located just a few blocks away, occasionally even staying overnight. As Beller puts it, her actions seemed to convey: “I have my own life. Treat me as if I don’t matter, and I won’t be around.

In early 1999, Carolyn, always vigilant about those who didn’t truly support her husband John, and mindful of hangers-on and false friends, resumed her role as his most steadfast supporter at the George offices. She had been absent for nearly two years, choosing to stay away while her husband tirelessly fought to keep the struggling magazine afloat.

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

It’s incredibly sad to reminisce about the most joyful instances shared by Carolyn and John, those precious moments when they could genuinely savor one another’s company, free from any sense of being invaded or pressured to entertain an audience.

For instance, their intimate September 21, 1996, wedding took place under candlelight before just 40 attendees at a secluded location on Cumberland Island – a venue that was so unassuming it lacked electricity for the church.

Gustavo Paredes, who had managed Jackie Kennedy’s Hyannis Port house for a long time, recounted that John Kennedy told him during the summer of 1994 that he never really bought into stories about encountering “the one,” as he believed such an immediate connection wasn’t common in real life. In this case, instead of using formal names like Caroline Kennedy and John F. Kennedy, you could use their first names for a more casual read: Gustavo Paredes, longtime manager of Jackie Kennedy’s Hyannis Port house, remembered John telling him that he never truly believed in stories about meeting “the one.” He thought such an instant connection was not common in real life.

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

Ariel Paredes shared with Beller that they were deeply connected, not only expressing strong affection but also standing up for each other fiercely.

Betsy mentioned that the photos from her 1998 Miami wedding depicted Carolyn and John as being deeply in love and filled with zest for life. This is the image of them that I carry with me, a time when they felt secure.

On July 18, 1999, as officials transitioned the search for John’s plane from a rescue to a recovery operation, 20 North Moore Street transformed into a place of memorial.

Since Carolyn wasn’t coming back, photographers instead captured images of the candles, flowers amassed at the front door, and the multitude of people who visited Tribeca to express their condolences.

People who knew about the problems between Carolyn and John shared with Beller that it wasn’t until many years had passed, even long after the couple was no longer around, that they truly understood the challenges faced by the individual who had been enveloped by Kennedy mania.

According to Sasha Chermayeff, a longtime friend of John’s who also became close to Carolyn, it might appear as if she was exaggerating the situation at that moment. Even those who were her closest friends and her husband often failed to recognize its true nature.

Sasha went on to say, “Initially, everyone seemed to expect her to solve the problem herself, C’mon, sort this out… Looking back, it’s clear that she didn’t truly have support around her at that time. This lack of presence from others only made her feel more alone, intensifying her fear and anger. However, considering the circumstances, her anger was justified.

2025-02-14 12:29