The brief, ironic life of Carolyn Bessette-Kennedy

For someone who has been gone from us for 25 years, Carolyn Bessette-Kennedy is having a remarkable second act. And it’s not just because of the spate of new books that mark the 25th anniversary of her death – along with that of her husband, John F. Kennedy Jr., and her sister, Lauren Bessette – when the plane he was piloting crashed off the coast of Martha’s Vineyard on July 16, 1999.

The fangirl “Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy” by Elizabeth Beller, the tabloid-y “Ask Not: The Kennedys and the Women They Destroyed” by Maureen Callahan and the sober, kaleidoscopic “JFK Jr: An Intimate Oral Biography” by RoseMarie Terenzio and Liz McNeil offer a “Rashomon”-like portrait of a complex woman, who has been described as both loving and self-centered.

But more than that is the phenomenon of Bessette-Kennedy’s embrace by a new generation on social media, especially TikTok, as the goddess of quiet luxury. This is best exemplified by the elegiac coffee-table book “CBK: Carolyn Bessette-Kennedy, a Life in Fashion” by Sumita Kumar Nair, which juxtaposes the former Calvin Klein public relations executive’s minimalist style – shirts, pants, and dresses in black, beige and white, red lipstick offset by spare makeup; straight blond hair swept back in a chignon – with the same looks interpreted for today.

That many of the photographs of her on the Internet and in Nair’s book are not only from official events with her husband but shots from the paparazzi who hounded her and whom she hated is the first – but not the last – irony in her brief life. (For those who say that a publicist should’ve had a better handle on her own press, remember that these men stalked and cursed her. She felt physically threatened by them. Plus, a publicist is a behind-the-scenes person. And, as any writer will tell you, it’s easier to deal with the press when the subject is someone or something other than yourself.)

No one called her “CBK” in her lifetime; nor was she beloved as a woman of class and grace as she is today, especially when favorably compared to the oft-criticized Meghan, Duchess of Sussex, who has adopted a similar sartorial style. In her time, Bessette-Kennedy was viewed as an ice princess from Greenwich, but here again ironies abound. 

She was born on Jan. 7, 1966 in White Plains to a middle-class French Canadian-Italian-American family. Her mother, the former Ann Marie Messina, was a strong-minded schoolteacher; her father, William, an intense civil engineer who traveled a good deal for work. Her parents divorced when Bessette-Kennedy was 8, and, according to Beller’s “Once Upon a Time,” her mother and the children – Carolyn and older twin sisters Lauren and Lisa – struggled until Ann married the widowed Richard Freeman, M.D., chief of orthopedic surgery at White Plains Hospital, and moved with the girls to his home in neighboring Greenwich.

We tend to view the past through the lens of the present, but neither White Plains Hospital nor Greenwich was the powerhouse each is today, with the hospital an expanding five-star medical center and Greenwich a mecca for Wall Street wealth. Bessette-Kennedy grew up in an upper-middle-class household on Lake Avenue, one of the serpentine thoroughfares that now constitutes the town’s tony backcountry. But the family hardly moved in Kennedyesque circles. Instead the fashionable, fun-loving Bessette-Kennedy – who transferred from Greenwich High School to the stricter St. Mary’s High School at her mother’s behest – earned money babysitting and working at the sporting goods store Threads & Treads. and at Caldor, the discount department store that had locations in nearby Port Chester and Greenburgh. 

“…As teenagers we had both worked for Caldor, she behind the jewelry counter and I at the customer service desk,” Carole Radziwill, Bessette-Kennedy’s close friend and cousin by her marriage to JFK Jr.’s cousin Anthony Radziwill, writes in her poignant 2005 book “What Remains:  A Memoir of Fate, Friendship & Love.” “What were the odds that John would (also) bring home a girl from Caldor?”

It was something the tight quartet joked about – and their circle noted.

“Carolyn was beautiful, intense, funny, smart, but if you could pick on her for one thing, it would be that she came from…what, a Connecticut upper-middle-class background that wasn’t blue blood,” Sasha Chermayeff, a JFK Jr. Phillips Andover Academy classmate, observes in “JFK Jr: An Intimate Oral Biography.” 

But Bessette-Kennedy – who had been steeled by her parents’ divorce, her maternal family’s independent work ethic and a career dealing with Calvin Klein’s VIP clients, which is how she met JFK Jr. – was no pushover. What emerges in all these books is a Bessette-Kennedy who was fiercely protective of herself, her husband and her inner circle even as she held the public at a remove with her glamorous, disengaged presence. 

In that she evoked another self-possessed child of divorce who grew up not quite as wealthy as those around her – the mother-in-law she never met. It was a bone of contention with Bessette-Kennedy that JFK Jr. never introduced her to his mother, Jacqueline Lee Bouvier Kennedy Onassis, who died on May 19, 1994, the same year they became an exclusive couple, and who would’ve been 95 on July 28. In a sense, JFK. Jr., deeply attached to his mother, married a woman who had a good deal in common with her – including a use of fashion as a kind of public armor that nonetheless piqued curiosity rather than diminish it.

“It’s not a style that calls attention,” Chloé creative director Gabriella Hearst writes in the foreword to “CBK.” “It is a style that tries to deflect attention, and by deflecting that attention, she’s making people pay more attention.”

Would Bessette-Kennedy and Onassis have been friends? Would Bessette-Kennedy’s marriage to JFK Jr. have lasted? Would there have been children? Would he – a man who was said to have been hyper, kind, charismatic, intellectually curious but also trapped in a public image – have run for president? What kind of first lady and woman would Bessette-Kennedy have been in her later years?

We’ll never know. She flies away from us forever – like Jackie or Princess Diana, another vulnerable but steely blue-eyed blonde, careening in their dark cars to their destinies.

Only to return, because that’s what icons do:  They return, transmogrified.  And that is perhaps the ultimate irony:  The woman once vilified as not being good enough for “America’s prince” has become in the retrospective haze of revisionist history, the woman we loved.