EXCLUSIVE: The Affair That Left JFK Jr. Completely Shattered — Radar Lifts the Lid on How Carolyn Bessette Cheated With a Calvin Klein Underwear Model Before the Famous Couple's Tragic Fate
JFK Jr. was left shattered after Carolyn Bessette's affair with a Calvin Klein model before their tragic fate.
Sept. 19 2025, Published 6:00 a.m. ET
JFK Jr. believed his wife, Carolyn Bessette-Kennedy, was having an affair – and it destroyed him, RadarOnline.com can reveal.
26 years later, shocking details emerge about his wife and a male model.
JFK Jr's Fears
Michael Bergin once described his secret relationship with Carolyn Bessette-Kennedy in 'The Other Man.'
John told a few close friends his worst fear was that Carolyn was cheating on him. And that dread was not unwarranted.
Carolyn had rekindled a relationship with former boyfriend Michael Bergin, revealed author Edward Klein in his blockbuster tell-all book The Kennedy Curse: Why Tragedy Has Haunted America's First Family for 150 Years.
Bergin – who himself wrote about his relationship with Carolyn in The Other Man: John F. Kennedy Jr., Carolyn Bessette, and Me – was a former underwear model Carolyn had met and fallen for when they were both working for Calvin Klein.
"Michael lived in a second-floor walk-up in Greenwich Village, and I was in his apartment one day ... when he was buzzed on the intercom from the apartment building front door," one of Bergin's friends said, Klein wrote.
The friend said: "Michael asked me to leave immediately, and when I went out, I found Carolyn Bessette-Kennedy hiding under the staircase."
Author Edward Klein wrote, Kennedy confessed, her renewed affair with Bergin during a fight.
"I said, 'Hi, Carolyn, what are you doing?' And she said, 'Oh, hi, I'm just going upstairs to Michael's.' When I got home, Michael called me and said in a kind of panic, 'You saw Carolyn! Why did you talk to her?' He really loved Carolyn and wanted to protect her."
Carolyn was able to keep her relationship with Bergin a secret – for a while, according to the book. Then, during one of the many screamfests she had with JFK Jr., she blurted out the truth.
John was thunderstruck and in "his narcissistic self-absorption, he found it inconceivable that a woman would choose another man over him," wrote Klein.
Ending In Tragedy
Kennedy Jr. went on to marry Calvin Klein publicist Carolyn Bessette in 1996.
"It took time for him to recover from this devastating blow, but eventually he convinced himself that his wife's behavior was more a reflection on her than on him."
Eventually, John moved out of their Tribeca loft and into a $2,000-a-night suite at the Stanhope hotel on Fifth Avenue. The chain of events eventually led to tragedy.
Carolyn's sister, gorgeous Morgan Stanley investment banker Lauren Bessette, suggested the three of them meet for drinks in the bar at the Stanhope.
Lauren was able to defrost an icy silence between John and Carolyn.
Lauren Bessette urged her sister Carolyn to join John on a flight to Hyannis Port.
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"Lauren was aware Carolyn had vowed never to fly with John in his plane," wrote Klein. "But as she squeezed her sister's hand, Lauren urged her to make an exception and accompany her husband in his Piper Saratoga the next day to Hyannis Port, where family members and friends were assembling for the wedding of his cousin Rory Kennedy."
Then, "for added encouragement," Klein added: "Lauren offered to fly along with the couple as far as Martha's Vineyard, where she planned to spend the weekend with friends. The three of them would make the flight together from Fairfield, New Jersey."
John, then Carolyn, agreed to Lauren's offer.
"'Great,' Lauren said. 'Then I'll see you guys tomorrow at the airport,'" Klein recounted.
The July 1999 plane crash near Martha's Vineyard claimed the lives of John, Carolyn, and Lauren.
That tomorrow was July 16, 1999 – the day the JFK Jr.-piloted plane crashed into the waters off Martha's Vineyard, killing all three of them.
But the secret about Carolyn's alleged affair didn't die with them.
"Years later, the proof that it happened came out," said an insider. "And we saw just how toxic Carolyn and JFK Jr.'s marriage was. They really were doomed."
