Joshua Goldman
Joshua Goldman
min read · August 16, 2025 · Entertainment

The Dark Side of Camelot: Carolyn Bessette's Hidden Struggles

Carolyn Bessette's marriage to JFK Jr is depicted as a fairy tale. In truth, it was more of a horror movie (pictured in 1996)

The Dark Side of Camelot: Uncovering the Troubled Marriage of JFK Jr and Carolyn Bessette

As we're treated to the sanitized version of John F. Kennedy Jr.'s life in CNN's latest docuseries, "American Prince," it's time to peel back the layers and reveal the truth behind his ill-fated marriage to Carolyn Bessette. According to insiders who knew them well, this so-called "Golden Couple" was actually a recipe for disaster.

Let's start with Ann Bessette, Carolyn's mother, who had some serious reservations about her daughter's relationship with JFK Jr. At the rehearsal dinner, she stood up and dropped a bombshell: "I hope my daughter has the strength for this." The stunned silence that followed spoke volumes about the concerns surrounding this union.

No one had ever spoken to John F Kennedy Jr like that. No one had ever told him the truth: That unlike his public image, he could be thoughtless at best, entitled at worst, and had a death wish that put at least one ex-girlfriend in mortal danger multiple times

But what exactly was going on behind closed doors? Sources close to Carolyn reveal that she had always been driven by a desire for a big life – and marrying into one of America's most iconic families was her ticket to fame, fortune, and validation. Having grown up with an absent father figure, William Bessette, Carolyn's need for love and attention from powerful men became an all-consuming force in her life.

Her meteoric rise as a Calvin Klein PR guru only fueled this obsession. She worked tirelessly to cultivate an image that screamed "Upper East Side, First Lady-in-Waiting," while secretly struggling with the weight of her new role. One friend described her as "so f*ed up" – and it's clear why.

The media narrative has long portrayed JFK Jr as a charming, down-to-earth guy who was swept off his feet by Carolyn's aloofness. But insiders paint a different picture: John was thoughtless, entitled, and had a death wish that put at least one ex-girlfriend in danger multiple times.

Friends of Carolyn told me that, contrary to the media spin, she worked very hard to seem so carefree, so aloof to John, all the while cultivating a look and image that read less downtown fashion girl and more Upper East Side, First-Lady-in-Waiting

Carole Radziwill, self-proclaimed best friend of Carolyn's, tries to spin the narrative in the doc, claiming that Carolyn made JFK Jr feel like he could be himself. But even she concedes that Carolyn was initially hesitant about marrying John – and for good reason.

As we delve deeper into the lives of this ill-starred couple, it becomes clear that Carolyn was desperate to escape her old life as a model and find a new sense of purpose in her marriage. Her friends describe her as "fucking herself" with John's neediness, often sacrificing her own needs for the sake of their relationship.

But what about JFK Jr himself? Behind his charming facade lies a complex web of insecurities and entitlement issues. His family's history, wealth, and fame had created an aura of invincibility around him – and he was determined to maintain that image at all costs.

When it came time for the couple to make their debut as a married team at his cousin's wedding in Hyannis, JFK Jr made one final demand: Carolyn would have to get on his plane with him, no matter what. It was the perfect opportunity for them to put on a united front and squash any divorce rumors.

But little did they know, that fateful July 16th weekend would prove to be their last together. As we delve deeper into the tragic events that unfolded, one thing is clear: the Kennedys' fairy tale had become a horror movie – and Carolyn Bessette was about to find out just how dark it could get.