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What Carolyn Bessette's friend told me about the senseless self-harm that made her 'start to die'. She desperately wanted to be the new Jackie Kennedy... how utterly deluded: MAUREEN CALLAHAN
Maureen Callahan · 2026-04-11 · via News | Mail Online

The latest Kennedy wife to be reinvented is hardly alone in being blamed for her husband's misery.

That list is, regrettably, long.

But Carolyn Bessette is the only one drawing comparisons, yet again, to Jacqueline Kennedy Onassis.

Mainstream and social media insist that the two were twin souls: Glamorous, elusive, captivating to men who could have any woman on the planet.

In truth, the two could not be more diametrically opposed.

But such is the impact of nostalgia, perfectly packaged by Hollywood producer Ryan Murphy in his glossy, global-hit series Love Story: A heady brew of 1990s New York City, that last pre-9/11, pre-Internet moment when fashion, magazines, nightlife, celebrity and tabloid media not only mattered, but collided in a final starburst.

A moment when celebrity was harder to achieve than engaging in the ritual humiliations of reality TV, sex tapes or pornified selfies.

Should it be any surprise that the 'Love Story' of Carolyn and John F Kennedy Jr has struck such a nerve?

Or that everyone wants to believe that two gorgeous, stylish, privileged people who revived a fading American political dynasty were the real deal – the likes of which we'll never see again?

It's a seductive notion, to be sure.

But it is, in fact, a fairy tale — a dangerous one at that. And the mainstream media's proclamation of Carolyn Bessette as the heiress to Jackie O's legacy is Exhibit A.

The latest Kennedy wife to be reinvented is hardly alone in being blamed for her husband's misery. But Carolyn Bessette is the only one drawing comparisons, yet again, to Jacqueline Kennedy Onassis.

Mainstream and social media insist that the two were twin souls: Glamorous, elusive, captivating to men who could have any woman on the planet. In truth, the two could not be more diametrically opposed.

The headline: 'Meet the Mrs', accompanied by a full-bleed paparazzi photo of Carolyn looking straight at the camera, John Jr in profile, leaning into her ear and failing to get her attention, on the cover of New York magazine's October 7, 1996 issue.

The subhead: 'What does John Kennedy Jr see in Carolyn Bessette? What she wants him to see: A woman who is bright, beautiful, and ambitious — like his mother.'

And so began this most unholy consecration, published weeks after their secret wedding on Georgia's Cumberland Island.

The headline, by the way, wasn't wrong. Jackie was exactly who Carolyn wanted John to see.

Inside, the article, entitled 'Instant Princess', sought to explain how Bessette, a civilian, had pierced John's rarefied world and made herself, not any of the movie stars or supermodels at his disposal, The One.

The article posited that Bessette was that most '90s of women: A 'Rules Girl' turned American royal.

The unlikely bestselling book of the era reads like today's trad-wife movement. 'The Rules: Time-Tested Secrets for Capturing the Heart of Mr Right,' said that feminism had done single women no favours.

The thesis: 'Men want a challenge. Don't talk to a man first. Don't see him more than once or twice a week. No more than casual kissing on the first date. The goal? Marriage, in the shortest time possible, to a man who you love, who loves you even more than you love him.'

Here's the thing: Jackie would never.

While Carolyn would pretend to be off living a fabulous life, hoping to make a noncommittal John Jr jealous, she was often, one friend told me, holed up in her grim studio apartment for weekends on end.

Not for America's most sophisticated future First Lady were such small-minded ideas.

At age 21, still a senior at George Washington University, Jackie Bouvier won Vogue's vaunted Prix de Paris essay contest in 1951, beating nearly 1,300 candidates.

Jackie's was a restless and searching mind.

She began working in journalism at a young age, and spent her life dedicated to words, ideas and books.

Carolyn Bessette, by contrast, graduated Boston University, where she appeared in a 'Girls of B.U.' calendar and worked in nightclubs.

At age 21, still a senior at George Washington University, Jackie Bouvier won Vogue's vaunted Prix de Paris essay contest in 1951, beating nearly 1,300 candidates. Jackie's was a restless and searching mind. She began working in journalism at a young age, and spent her life dedicated to words, ideas and books.

Carolyn Bessette, by contrast, graduated Boston University, where she appeared in a 'Girls of B.U.' calendar and worked in nightclubs.

Jackie and Carolyn did have a few things in common: Difficult fathers, the determination to marry important men, style and star power all their own.

But that's where the similarities end.

Jackie was erudite, curious, a voracious reader, well-traveled and cultured, interested in art, classical music, dance, interior design, history, architecture and literature.

When senator John Kennedy waffled on marriage, Jackie did what most women could only dream of: She flew off, on assignment, to cover the coronation of Queen Elizabeth.

She really did have better things to do.

Carolyn, by contrast, told John she'd 'think about' his proposal of marriage — as a means of control.

Jackie also entered her marriage honestly: She wanted to have babies, a prerequisite for any wife of a future US president.

She suffered greatly in this, enduring a miscarriage, a stillbirth and, shortly before JFK's assassination in 1963, the death of her baby Patrick in the first hours of his life.

The Kennedy family blamed Jackie and her smoking habit. They did not blame JFK, whose promiscuity had likely infected Jackie with sexually transmitted diseases that affected her ability to carry healthy babies to term.

Jackie bore it all without complaint.

Carolyn, by contrast, refused John the children he so badly wanted — to the point where he had told friends that he'd chosen the name Flynn for a son.

According to her ex-boyfriend Michael Bergin, a Calvin Klein underwear model, Carolyn had at least one abortion and a self-reported 'miscarriage' while dating JFK Jr.

And after their marriage, she continued smoking, using cocaine, drinking and losing weight.

Carolyn's default position, as a Kennedy wife, was to deny him.

According to John's friend Steven Gillon, Carolyn also enjoyed humiliating John, confiding embarrassing details of their sex life to mutual pals and, in her most painful rejection, refusing to have sex with him in the months before their 1999 deaths.

JFK Jr, the most desired man in America, neutered by a regular girl from Connecticut.

Jackie and Carolyn did have a few things in common: Difficult fathers, the determination to marry important men, style and star power all their own. But that's where the similarities end.

Jackie entered her marriage honestly: She wanted to have babies, a prerequisite for any wife of a future US president.

John asked Gillon back to the Manhattan apartment he shared with Carolyn in 1996, to look at a letter from execs at Hachette, publisher of his failing magazine, George.

That letter, in effect, called John 'lazy and stupid.' It made clear that the company would not continue publishing George, another humiliation.

Carolyn was infuriated — not at Hachette, but her husband.

'Everybody f***s you, John, and you just take it!' she yelled. 'You let everybody f*** you, John. When are you going to grow some balls and start fighting back? You need to start f***ing people back, John.'

Jackie, no matter what JFK put her through, would never have excoriated him in public. She had too much respect for the presidency, her husband's reputation, and most importantly — herself.

In a series of retrospective interviews given to historian Arthur Schlesinger in 1964, Jackie said she considered it part of her job as a political wife to give her husband 'a climate of affection and comfort and détente.'

Even as political advisers thought her a hindrance, her husband refused to ask her to change.

'I was always a liability to him,' she told Schlesinger of their early days. 'Everyone thought I was a snob who had bouffant hair and had French clothes and hated politics.'

As it turned out, the American people loved Jackie for all of it — women, especially. She was the first young, glamourous, most stylish First Lady the nation had ever known, but she was also authentically herself.

Who was Carolyn Bessette? It's likely that even she didn't know.

Carolyn was interested in none of what Jackie enjoyed or represented.

Fashion, personal appearance and social climbing were Carolyn's preoccupations — as was her reported years-long strategy in meeting, seducing and marrying John F Kennedy Jr.

'She knew she possessed all these qualities to make herself a kind of an "It girl", said one observer at the time. 'She knew all these talents were going to take her somewhere, but it wasn't as if she was a career girl. She had social power, and this sort of odd mystery that eventually was going to land her a situation like the one she has. To me, when I look at this couple, it's a very simple guy; it's a very complicated girl.'

But the Carolyn depicted in Love Story isn't complicated at all.

She isn't conflicted about the fame she so desperately seeks. She doesn't have a serious cocaine habit, as Carolyn did. She isn't physically violent and abusive, as her ex-boyfriend Bergin later detailed and as John's friends always suspected. And she isn't cheating on her husband with Bergin throughout her marriage, all of which Carolyn did in real life.

Perhaps producer Ryan Murphy thought these inconvenient facts would make his fictional Carolyn harder to root for or impossible to love.

If so, that's a shame, because viewers were robbed of a psychologically complex and haunted woman, one whose story is an object lesson: Be careful what you wish for.

And remember that American royalty is an oxymoron.

Carolyn, by contrast, refused John the children he so badly wanted. According to her ex-boyfriend Michael Bergin (pictured), a Calvin Klein underwear model, Carolyn had at least one abortion and a self-reported 'miscarriage' while dating JFK Jr.

Carolyn (pictured with Bergin) also enjoyed humiliating John, confiding embarrassing details of their sex life to mutual pals and, in her most painful rejection, refusing to have sex with him in the months before their 1999 deaths. 

As Steven Gillon wrote in his 2019 biography, America's Reluctant Prince, John went so far as to secretly commission an investigation into Carolyn while they were dating.

A friend who, Gillon writes, 'had connections in the Manhattan nightclub scene,' puts the difference between Bessette and Bouvier in stark relief.

'[Carolyn] does a lot of blow, she stays out late, she knows how to reel in guys and play guys, she dated the star football player in high school, the captain of the hockey team in college. Be careful.'

If anyone needed to be careful here, it was Carolyn.

Had she been able to order a similar investigation into John, she would have learned — contrary to his impeccable image — that he not only had a death wish, but a pathological habit of bullying his girlfriends into risking their lives.

Little surprise that this salient characteristic was also left out of Love Story. After all, it's not a fairy tale if the handsome prince is constantly trying to kill himself and take his princess bride with him.

Ironically, Jackie herself built the myth that her future daughter-in-law fell prey to.

Camelot was a total fabrication, one Jackie insisted upon memorializing in Life magazine days after her husband's assassination.

She thought it her best chance at salvaging her husband's short presidency, by most measures a failure: The Bay of Pigs, the Cuban Missile Crisis, the escalation of troops to Vietnam.

Jackie, however, would have several more reincarnations: notably as the wife of Greek shipping magnate Aristotle Onassis, then as a single, liberated career woman in New York City.

Carolyn, who went down in John Jr's plane at age 33, never had that chance. But would she have ever left John, let alone had the internal resources, or substantial interests, to reinvent herself?

All that access to presidents and powerbrokers, a platform like no other – and what did Carolyn do with it?

She shopped, she chain-smoked, did cocaine in Herculean amounts, cheated with ex-boyfriends and felt sorry for herself.

Noted American academic and provocateur Camille Paglia said as much back in 1999, comparing JFK Jr to Paul McCartney and Carolyn to Linda Eastman.

'In both cases,' she said, 'you have an outgoing, warm, pretty-boy who takes into his life an often petulant, very private woman who is introverted to the point of neurosis… one would hope that the wife of a man like JFK Jr would extend him outward and broaden him. But she may have paralyzed him.'

Carolyn was 30 years old when she married John.

Jackie was only four years older than that, and the mother of two small children, when her husband was assassinated, his brains blown all over her.

Only one of these women comported herself with dignity. Only one of these women could not abide public pity.

The other engaged in a physical, public brawl with John in a New York park, spat in the face of a female paparazzo and verbally castrated her husband in front of his friends.

Carolyn was 30 years old when she married John. Jackie was only four years older than that, and the mother of two small children, when her husband was assassinated, his brains blown all over her.

Only one of these women comported herself with dignity. Only one of these women could not abide public pity. The other engaged in a physical, public brawl with John in a New York park, spat in the face of a female paparazzo and verbally castrated her husband in front of his friends.

Carolyn knew full well what she was getting into — so much that while they were dating, she began remaking herself from a fashion-world hipster into a future First Lady.

As I wrote in my book, Ask Not: The Kennedys and the Women They Destroyed, her transformation was one of discipline and deliberation.

Carolyn's lifelong aversion to exercise gave way to secret classes in the Lotte Berke Method. She dropped twenty pounds, straightened her unruly hair and bleached it platinum blonde, began dressing in minimalist Japanese masters such as Yohji Yamamoto and carrying $30,000 Hermés Birkin bags.

Longtime friends of Carolyn's found themselves cut off. As one told me: 'John wanted certain people out of her life. They were grooming Carolyn to be John Kennedy's wife, and John Kennedy was being groomed to go into politics. I think the problem is that Carolyn created this Stepford political wife to please John. That's when she started to die.'

Had Carolyn more to offer than style and beauty, perhaps she would have felt more confident in cutting her spoiled, entitled, limited husband loose long before that fatal plane crash.

And if the mass media had told the truth about Kennedy men — that they were all-too-often drunk, reckless, thoughtless and a mortal danger to women — perhaps Carolyn wouldn't have fallen as hard for the myth as the man.

In the aftermath of the July 16, 1999 plane crash that killed JFK Jr, Carolyn and her sister Lauren, there was a rush to enshrine Carolyn with a gravitas she did not possess.

American scholar Paglia was a lone voice of reason.

'She was no Jackie!' Paglia said at the time. 'It's absurd. What did that woman do with the enormous opportunity presented to her as the wife of John F. Kennedy Jr? She did nothing.'

Jackie pushed through her grief and trauma as a newly widowed young mother, and in the immediate aftermath signaled to the world that America would not just survive the assassination of its young president but emerge stronger for it.

Carolyn? Carolyn… went shopping.