Even before her roller-coaster love story with John F. Kennedy Jr., Carolyn Bessette had a type: beautiful men with power and influence.
There was Alessandro Benetton, an heir to the clothing fortune; Will Regan, the nightlife impresario behind Manhattan hotspots like Rex and, later, Lotus; and one of her great romances, Calvin Klein model Michael Bergin.
Kennedy was People’s “Sexiest Man Alive” in 1988, but Bergin, a friend of Bessette’s said, gave him a run for his money.
Even before her roller-coaster love story with John F. Kennedy Jr., Carolyn Bessette had a type: beautiful men with power and influence — including Calvin Klein model Michael Bergin. Joey Andrew/startraksphoto.com
Bergin met Bessette in the ’90s while both were working for Calvin Klein. He later went on to a role in “Baywatch.” Courtesy Everett Collection
“He was a breathtaking man. He was a real beauty,” the friend told Page Six.
So much so, the source said, that John was jealous.
“Do I think she used Michael to get John jealous? I think Michael got John jealous. Carolyn was too smart, not to not be aware of that … She loved Michael,” a source close to both Bergin and Bessette said.
Sources also believe that Bessette’s feelings for Bergin, who starred on “Baywatch” for 88 episodes from 1997 to 2001, never completely went away even after she married Kennedy.
Bergin claimed in his 2004 book “The Other Man: A Love Story,” that he and Bessette continued their relationship after she was with Kennedy. He also “Good Morning America” that the affair “was wrong — on my part — and her part.” Joey Andrew/startraksphoto.com
“They still had a lot of chemistry,” the source said, adding that Bessette was repeatedly “drawn back to” Bergin.
In fact, Bergin claimed in his 2004 book “The Other Man: A Love Story,” that he and Bessette continued their relationship after she was with Kennedy. He also told “Good Morning America” that the affair “was wrong — on my part — and her part.”
While Bessette could come across as aloof — even on the FX series “Love Story,” Bergin (played by Noah Fearnley) tells Carolyn (Sarah Pidgeon) that she “is the most guarded and elusive woman I’ve ever met” — sources recall her being more calculated in real life.
“She was very aware of her appeal,” the source told Page Six.
“They still had a lot of chemistry,” a source told Page Six of Bergin and Bessette, adding that Bessette was repeatedly “drawn back to” him. Ron Galella Collection via Getty Images
“She was beautiful. She had the full package. When she was talking to you — everyone [else] disappeared. It was just her and you. She made you feel like you were the most interesting and attractive person she had ever met,” the source added.
While still living in Boston, where she went to college, Bessette may have manifested becoming Mrs. JFK Jr. before she met Kennedy, according his friend Steve Gillon in the biography “America’s Reluctant Prince.”
“I’m going to move to New York and I’m going to get him,” she told a friend at Boston University in 1988, according to the book.
Before that happened, though, Bessette bided her time with notable men.
While Bessette could come across as aloof — even on the FX series “Love Story,” Bergin (played by Noah Fearnley, above) tells Carolyn (Sarah Pidgeon, above) that she “is the most guarded and elusive woman I’ve ever met” — sources recall her being more calculated in real life. Steve Sands/ New York Newswire / BACKGRID
She dated NHL star John Cullen, who later played for the Pittsburgh Penguins and Tampa Bay Lightning, while they both attended BU.
Then there was the fling with Benetton, the Italian clothing heir, while she was working as a sales person at a Calvin Klein Boston boutique around 1989.
Benetteton was “mesmerized” by Bessette, he wrote in his 2022 memoir, gushing, “I liked her instantly.” The pair shared romantic dinners at the Waldorf and coastal weekends in Maine and on Martha’s Vineyard.
By the time Bessette moved to New York in the early ’90s, and got her break as a fashion publicist at Calvin Klein, she was gliding past the velvet ropes at New York nightclubs like Rex — where she sparked a relationship with owner Regan.
Bessette dated nightlife impresario Will Regan (right) not long after she moved to New York in the early ’90s. Patrick McMullan via Getty Images
Describing Regan as an “alpha,” the friend said. “He was intelligent. He was driven. He was the kind of guy that a woman [like Carolyn] would want. He came from an upper middle class family.”
Meanwhile, through her job at Calvin Klein — she was by then dressing celebrities for the brand — “young men with power and influence were hitting on her frequently,” a source told The New York Times. “She’s had offers of courtship and marriage from every Saudi prince from here to the Middle East in those clubs.”
But it was her on-and-off romance with Bergin — famous for his washboard abs in Klein’s ubiquitous underwear ads — that was the biggest threat to her relationship with John.
Bessette met Bergin, originally from Waterbury, Connecticut, through their work for the fashion designer.
Bessette may have had her sights set on JFK Jr. before she even moved to New York: “I’m going to move to New York and I’m going to get him,” she told a friend at Boston College in 1988, according to Steve Gillion’s biography “America’s Reluctant Prince.” DAVE ALLOCCA / DMI
“Michael Bergin was really sweet, so beautiful. Men are not thought of as beautiful. He was. Beautiful body,” said the friend said. “He was fun to be with. He was a chick magnet.”
“Carolyn and I had a very intense love for each other,” Bergin told author Edward Klein in 2003, as reported by Vanity Fair. “We were inseparable for a couple of years.”
But Maureen Callahan, author of “Ask Not: The Kennedys and the Women They Destroyed,” recounted in the Daily Mail that Bergin’s 2004 memoir, “The Other Man: A Love Story,” claimed Bessette once physically assaulted him for talking to another woman at a party.
“She dragged me to the nearest corner … and took my face in her hands, literally burying her fingernails into my skin. ‘What the f–k do you think you’re doing?’ she hissed…” Callahan quoted from Bergin’s out-of-print book. “I turned and caught a glimpse of my face in a mirror. I had two bloody slits on each cheek from where Carolyn’s nails had burst through the skin.”
Bergin claimed Bessette once physically assaulted him for talking to another woman at a party, according to author Maureen Callahan. Courtesy Everett Collection
But then Bessette met Kennedy, the man she’d wished to snare — reportedly during a suit fitting at Calvin Klein in 1992, according to Elizabeth Beller’s 2024 biography, “Once Upon a Time.”
(“If [Klein] could have gotten JFK. Jr. to be the underwear model he would have,” said the source.)
Others recall a more strategized meet-cute.
“Carolyn found out which bar John Jr. frequented and went there and that’s how they met. Not through Calvin,” Callahan writes in her book,
Two months into their new romance in the summer of 1992, Beller writes, Kennedy received an ominous letter from an unnamed sender — claiming Carolyn was only dating him for his fortune and fame, according to Beller’s biography.
Bergin has claimed Bessette went back to him after Kennedy dumped her — though the “Love Story” couple later reunited. STR New
He broke up with her at El Teddy’s in Tribeca, and they stayed that way for a year. During that time, Bessette went back to Bergin.
“She was constantly drawn back to Michael Bergin,” the friend said. “She was very in love with him, they had a real connection. I don’t know that they had a hard ending.”
The source told Page Six that Bessette’s relationship with the model got under JFK Jr.’s skin — so much so it may have made Kennedy regret the break-up.
In 1993, Kennedy — who had been dating Daryl Hannah on and off after meeting Bessette — desperately tried to get Bessette back.
Paul Kelly plays Kennedy in “Love Story,” opposite Sarah Pidgeon as Bessette. Kurt Iswarienko/FX
“John was always crazy about her,” the friend added. “He was more in love with her. That’s why it was more attractive.”
Bessette felt entitled to Kennedy’s attention, sources said — an attitude that set her apart from his past relationships with the likes of Hannah and Sarah Jessica Parker.
The source noted, however: “There are many people who felt she used Michael to get to John.”
According to Callahan, Bessette told Bergin in October 1993 that “she was pregnant, that the baby was his, and despite his willingness to raise the child with her, that she was going to have an abortion.”
In the end, Carolyn got her prince, marrying JFK Jr. in 1996 at a private ceremony off the coast of Georgia. 1.23.97
The model begged her to spend the weekend with him in Connecticut, Callahan writes. But Bessette refused.
Bergin apparently found out that Bessette was reunited with Kennedy when he saw the two, a month after the abortion bombshell, on the front page of The Post — watching the New York City Marathon together.
Nonetheless, Callahan writes, Bergin still accompanied Bessette to the abortion.
But she never quite let Bergin go. In early 1996, according to Callahan, Bessette allegedly called to tell Bergin she had been pregnant again, presumably by Kennedy, but lost the baby.
“Bergin writes that they spent that night together, and he still hoped he might win her back,” Callahan writes — quoting from Bergin’s book: “The way I saw it, she probably didn’t even tell John Jr. about the pregnancy.”
In the end, Bessette was torn between the free and easy life she lived with Bergin — and the appeal of Kennedy, even though she “didn’t really want all the trappings of being a Kennedy,” according to the friend, who added: “Being a celebrity is not something she wanted to be.”
Still, she and Kennedy were married that September. Three years later, they died in a plane crash along with her sister Lauren.
“I believe Michael was special enough that many people viewed him as a rival for John. But, at the end of the day, he [Michael] wasn’t John,” the source said. “She obviously wanted to marry John.”