Even before her roller-coaster love story with John F. Kennedy, Jr., Carolyn Bessette had the mold of a beautiful man with power and influence.
There was Alessandro Benetton, heir to a clothing fortune. Will Regan is the nightlife impresario behind such Manhattan hotspots as the Rex and later the Lotus. and one of her great romances, Calvin Klein model Michael Bergin.
Bergin, Bessette’s friend, said he gave Kennedy money after he was named People magazine’s “Sexiest Man Alive” in 1988.
“He was a breathtaking man. Truly beautiful,” a friend told Page Six.
Sources say John was extremely jealous.
“Do you think she used Michael to make John jealous? I think Michael made John jealous. Carolyn was too smart not to realize that…she loved Michael,” said a source close to both Bergin and Bessette.
Sources also believe that Bessette’s feelings for Bergin, who appeared on Baywatch for 88 episodes from 1997 to 2001, never completely disappeared after she married Kennedy.
“They still had a lot of chemistry,” the source said, adding that Bessette was “drawn back” to Bergin multiple times.
In fact, Bergin claimed in her 2004 book, The Other Man: A Love Story, that they continued their relationship after Bessette started dating Kennedy. He also told “Good Morning America” that the incident was “wrong for me and wrong for her.”
Although Bessette sometimes comes across as aloof on the FX series Love Story, with Bergin (played by Noah Fearnley) telling Carolyn (Sarah Pidgeon) that she’s “the most cautious, elusive woman I’ve ever met,” sources say she was more calculating in real life.
“She knew what she was attracted to,” a source told Page Six.
“She was beautiful. She had it all. When she was talking to you, everyone[other people]disappeared. It was just her and you. She made you feel like the most interesting and attractive person she had ever met,” the source added.
In her friend Steve Gillon’s biography “America’s Reluctant Prince,” Bessette notes that while she was still living in Boston and attending college, she may have become Mrs. JFK Jr. even before she met Kennedy.
“I’m going to move to New York and pick him up,” she told a friend at Boston University in 1988, according to the book.
But before that happened, Bessette was waiting for her time with a prominent man.
She later dated NHL star John Cullen, who later played for the Pittsburgh Penguins and Tampa Bay Lightning, and they both attended BU.
Then, around 1989, while she was working as a sales associate at a Calvin Klein boutique in Boston, she had an affair with Italian clothing heir Benetton.
Benetton was “fascinated” by Bessette, he wrote in his 2022 memoir, “I fell in love with her right away.” The two shared romantic dinners at Waldorf, Maine, coastal weekends, and Martha’s Vineyard.
By the time Bessette moved to New York in the early ’90s and made her break as a fashion spokesperson for Calvin Klein, she was weaving through the velvet ropes at New York nightclubs like Rex. That’s where my relationship with the owner, Regan, began.
said a friend who described Regan as “alpha.” “He was intelligent. He was driven. He was the kind of guy that women (like Carolyn) wanted. He came from an upper-middle-class family.”
Meanwhile, through her work at Calvin Klein (by then she was dressing celebrities for the brand), “young men with power and influence were frequently attacking her,” a source told the New York Times. “She’s had courtships and marriage offers from all the Saudi princes in these clubs, from here to the Middle East.”
But it was Klein’s on-and-off romance with Bergin, famous for her washboard abs in her ubiquitous underwear ads, that posed the biggest threat to her relationship with John.
Bessette met Bergin, a Waterbury, Conn., native, through her work as a fashion designer.
“Michael Bergin was really sweet and very beautiful. Men aren’t supposed to be beautiful. He was. He had a beautiful body,” said a friend. “He was fun to be around. He was a charming guy.”
“Carolyn and I had a very intense love for each other,” Bergin told author Edward Klein in 2003, Vanity Fair reported. “We were inseparable for several years.”
But Maureen Callahan, author of Ask Not: The Kennedys and the Women They Destroyed, detailed in the Daily Mail that Bergin claimed in her 2004 memoir, The Other Man: A Love Story, that Bessette physically assaulted her for talking to another woman at a party.
“She dragged me to the nearest corner, grabbed my face with both hands, and literally dug her nails into my skin. ‘What do you think you’re doing?’ she hissed…” Callahan quotes from Bergin’s out-of-print book. “I turned around and caught a glimpse of my face in the mirror. Carolyn’s nails had broken through my skin, making two bloody cuts on each cheek.”
But then Bessette met Kennedy, the man she was trying to ensnare — reportedly during a suit fitting at Calvin Klein in 1992, according to Elizabeth Beller’s 2024 biography Once Upon a Time.
(“If[Klein]had used JFK. Jr. as an underwear model,” the source said.)
Some recall more strategic encounters.
“Carolyn found John Jr.’s favorite bar and went there, and that’s how they met, not through Calvin,” Callahan wrote in his book.
According to Beller’s biography, in the summer of 1992, two months after their new romance began, Kennedy received an ominous letter from an anonymous sender who claimed that Carolyn was dating him only for her wealth and fame.
He broke up with her at El Teddy’s in Tribeca and they continued their relationship for a year. Meanwhile, Bessette returned to Bergin.
“She was always attracted to Michael Bergin,” said a friend. “She loved him very much and they had a real bond. I don’t know that they had a painful ending.”
Sources told Page Six that Bessette’s relationship with the model was in the vein of JFK Jr., which may have caused Kennedy to regret the breakup.
After meeting Bessette in 1993, Kennedy, who was dating Daryl Hannah on and off, desperately tried to win her back.
“John was always crazy about her,” the friend added. “He loved her more. That’s why she was more attractive.”
Sources said Ms Bessette felt entitled to Mr Kennedy’s attention, an attitude that set her apart from her past relationships with Hannah Parker and Sarah Jessica Parker.
But the source said: “There are a lot of people who feel she used Michael to get closer to John.”
According to Callahan, Bessette told Bergin in October 1993, “She was pregnant, the baby was his, and despite his willingness to raise the child with her, she intended to have an abortion.”
The model begged her to spend a weekend with him in Connecticut, Callahan wrote. But Bessette refused.
Bergin apparently learned that Bessette had reunited with Kennedy when she saw the two of them watching the New York City Marathon together on the front page of the Post a month after the abortion bombshell.
Despite this, Callahan writes that Bergin still accompanied Bessette to the abortion.
But she never let Bergin go. According to Callahan, Bessette allegedly told Bergin by phone in early 1996 that she had become pregnant again, possibly by Kennedy, but had lost the baby.
“Bergin wrote that he still hoped that he might spend that night with her and get her back,” Callahan writes, quoting from Bergin’s book.
In the end, Bessette was torn between the free and easy life she lived with Bergin and the charm of Kennedy, but “she didn’t really want all the trappings of being a Kennedy,” the friend said, adding that “becoming a celebrity wasn’t what she wanted.”
Still, she and Kennedy married that September. Three years later, they died in a plane crash along with their sister Lauren.
“I think Michael was special enough that a lot of people saw him as John’s rival, but at the end of the day, he wasn’t John,” the source said. “She obviously wanted to marry John.”
