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She Had It All… Until Love Asked Her to Let It Go

At the height of her high-powered Calvin Klein career, Carolyn Bessette was forced to leave her job so her husband, John F. Kennedy Jr., could take center stage.

Sasha Chermayeff, JFK Jr.’s best friend from high school, exclusively spoke with Page Six about why Bessette left her PR position with the American fashion house after marrying the son of President John F. Kennedy and Jacqueline Kennedy Onassis.

“She left her job basically because everything had to revolve around John and George magazine,” Chermayeff said, referring to the political lifestyle magazine Kennedy Jr. co-founded in 1995Carolyn Bessette-Kennedy and Calvin Klein walking together.

 

John F. Kennedy Jr. in a tuxedo and Carolyn Bessette-Kennedy in a white shirt and black skirt attend the Brite Night Whitney Fundraising Gala.

Chermayeff also claimed there was a “conflict of interest” for advertisers because of the magazine’s crossover with fashion. (The first issue’s cover famously featured supermodel Cindy Crawford dressed as George Washington.)

“She was supposed to sort of give up everything in order to make his career moves more palatable for the world, and I feel sad about it,” Chermayeff said, adding that in the ’90s, women “weren’t really as important.”

Chermayeff wondered what Bessette could have accomplished had she stayed in the industry.

John F. Kennedy Jr. at a press conference announcing the launch of "George" magazine, with a large display of the inaugural issue featuring a woman in a colonial-style outfit.
“She left her job basically because everything had to revolve around John and George magazine,” Sasha Chermayeff said, referring to his political magazine (seen here in 1995)
Calvin Klein and Carolyn Bessette-Kennedy attend the City of Hope fundraiser party.
Bessette (seen here with Klein in 1992) also left because there was a “conflict of interest.”Penske Media via Getty Images

“She was a very smart girl… She was very, very well-read. She was interested in all kinds of things,” Chermayeff reminisced.

After graduating from Boston University, Bessette started working for the brand as saleswoman at a store located in a Massachusetts shopping mall. While working the floor, she was noticed by a traveling sales coordinator and was offered a position at the flagship store in New York City.

Bessette quickly worked her way up and began dressing Klein’s high-profile clients like Annette Bening and Diane Sawyer.

After being noticed by the designer himself, Bessette quickly rose up the ranks to become the director of show productions.

John F. Kennedy Jr. and Carolyn Bessette-Kennedy walking on a city street.
“She was supposed to sort of give up everything in order to make his career moves more palatable for the world, and I feel sad about it,” Chermayeff said of Bessette (seen here with JFK Jr. in 1997)
John F. Kennedy Jr. in a tuxedo and Carolyn Bessette in a black dress, holding hands at a formal event.
Chermayeff described Bessette (seen here with JFK Jr. in 1998) as “very smart” and “well-read.”

Her reign at the clothing company came to an abrupt end when she quit her job following her and Kennedy Jr.’s 1996 nuptials.

Hulu and FX’s “Love Story” series — which is based on Elizabeth Beller’s novel “Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy” — portrays Klein as the person who initially introduced Bessette to the Kennedy scion.

Episode 6 depicts the heartbreaking moment Bessette (Sarah Pidgeon) informs Klein (Alessandro Nivola) that she is quitting.

“I hope you know how deeply indebted I am to you — for your mentorship, your friendship — you’ve changed my life,” she says. “You saw something in me and fostered it and for that I am forever grateful, truly.

“I think it’s become apparent that I can no longer serve you or this company in the way we both would like.”

Two people in a modern office, a man standing and a woman seated at a round table, from the "Love Story" episode 6.
Hulu and FX’s “Love Story” depicts Bessette (Sarah Pidgeon) quitting her job at Calvin in episode 6
Woman with long blonde hair looking down while wearing a gray sweater.Klein, taken aback, responds by telling her he didn’t think that was where the conversation was going.

“I just think my presence here has become a bit of a distraction,” she explains, “My whole job is to promote your work and I can’t do that to my full ability.”

Bessette went on to explain that she knows the mayhem surrounding her relationship is only “temporary,” to which Klein disagrees.

John F. Kennedy Jr. smiling while holding a book and wallet at a newsstand with "George" magazines on display.

“Don’t downplay it, Carolyn. You’re the realization of every woman’s dream. America’s son has chosen you. It’s not a temporary feat, it’s a masterstroke,” he spits back, before adding that he felt “blindsided.”

Bessette apologizes before walking out and leaving for good. The scene ends with Klein calling her out for choosing her friend, Narciso Rodriguez, to design her wedding gown over him.

John F. Kennedy Jr. kissing his wife Carolyn Bessette-Kennedy on the cheek.

In Thursday night’s episode, Bessette is seen struggling with the aftermath of leaving her job and feels lost without her PR position. Bessette then goes to a job interview with Klein’s competitor, Ralph Lauren, only to be stalked by the paparazzi on the way to the meeting.

While Bessette is grappling with her new life as Mrs. Kennedy, her husband is having issues with his magazine, from financial setbacks to disagreements with co-founder Michael J. Berman over the creative direction of the monthly mag.

The final issue of George Magazine was published in January 2001 — two years after Kennedy Jr. and Bessette died in a tragic 1999 plane crash. He was 38 and she was 33.