A former fashion publicist who married JFK Jr., Carolyn Bessette-Kennedy was just 33 when she died alongside her husband in a plane crash off the coast of Martha's Vineyard in 1999.
ZUMA Press, Inc./Alamy Stock PhotoCarolyn Bessette-Kennedy in March 1999, just months before she and JFK Jr. perished in a plane crash.
To many, Carolyn Bessette-Kennedy seemed like a princess in a fairy tale. She was tall, beautiful, blonde, and — as of 1996 — married to John F. Kennedy Jr., the dashing son of John F. Kennedy. But sometimes, she felt more like a prisoner in a tower than a princess in a castle.
“If I don’t leave the house before 8 a.m.,” she told a friend, “[the paparazzi are] waiting for me. Every morning. They chase me down the street.”
Indeed, Bessette-Kennedy’s life was not as charmed as it seemed. Not only was she hounded by the paparazzi, who routinely waited outside the New York apartment she shared with her husband, but she felt ill-suited for the Kennedy world, and her marriage with JFK Jr. had become strained.
Then, in July 1999, Bessette-Kennedy, her sister Lauren, and JFK Jr. all perished in a horrific plane crash off the coast of Martha’s Vineyard. Carolyn Bessette-Kennedy was just 33 years old at the time of the accident.
Since then, the full truth of her story has become harder to see than ever before. Different narratives have emerged about Carolyn Bessette-Kennedy, with some claiming she was a cocaine addict and a cheater and others insisting that she was effervescent, elegant, and eager to fix her marriage.
Here’s everything you need to know about Carolyn Bessette-Kennedy, the beautiful wife of John F. Kennedy Jr. — who died alongside him.
Carolyn Bessette’s Early Life, From Connecticut To Calvin Klein
Bessette FamilyCarolyn Bessette’s yearbook photo from St. Mary’s High School. 1983.
Born on January 7, 1966, in White Plains, New York, Carolyn Jeanne Bessette always stood out in a crowd. She was voted the “ultimate beautiful person” at her high school in Greenwich, Connecticut, and she appeared on the cover of the “Girls of BU” calendar while studying at Boston University.
After she graduated, Bessette went to a Calvin Klein store at a mall near Boston to apply for a sales assistant position. She was given the job on the spot, allegedly because of her resemblance to the Calvin Klein model Elaine Irwin. Shortly thereafter, a traveling sales coordinator recommended Bessette to Calvin Klein executive Susan Sokol, who was looking for an employee to handle Mr. Klein’s “celebrity clients” in New York City.
“Carolyn fit the bill perfectly,” Sokol told The New York Times. “She was absolutely charming, she was completely refreshing, she was completely outgoing. [She] wouldn’t feel intimidated working with these kinds of people.”
Carolyn Bessette thrived at Calvin Klein, where her style and poise enchanted clients like television broadcast journalist Diane Sawyer and the actress Annette Bening. Over the years, she climbed through the ranks from celebrity sales, to director of public relations, to director of show production.
It was at Calvin Klein, according to some sources, that Carolyn Bessette first crossed paths with her future husband John F. Kennedy Jr.
Becoming John F. Kennedy Jr.’s Wife
Brownie Harris/Corbis via Getty ImagesJohn F. Kennedy Jr. was considered one of America’s most eligible bachelors before he married Carolyn Bessette in 1996.
The exact details of Carolyn Bessette and John F. Kennedy Jr.’s first meeting are known only to them. Though some sources claim that they crossed paths at Calvin Klein when JFK Jr. wandered in for a fitting in 1992, others state that the couple met while they were running in Central Park. Whatever happened, sparks flew — but things didn’t fall into place right away.
The nature of Carolyn Bessette and JFK Jr.’s early courtship depends on who you ask. Some sources claim that JFK Jr. was immediately infatuated with Bessette, but that Bessette had her doubts. She was unimpressed by their first date, according to Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy (2024) by Elizabeth Beller, and JFK Jr.’s reluctance to introduce Bessette to his mother led her to break up with him several times.
Even when JFK Jr. proposed with a platinum ring that featured diamonds and sapphires, Beller writes, Bessette demurred. She told him she needed to “think about it” before agreeing to marry him three weeks later.
Tyler Mallory/LiaisonThough it was rumored that Carolyn Bessette-Kennedy lacked confidence in JFK Jr.’s piloting abilities, JFK Jr. himself insisted, “The only person I’ve been able to get to go up with me, who looks forward to it as much as I do, is my wife.”
However, other sources claim that Bessette was the one who pursued JFK Jr. at the beginning. Beller also reports that JFK Jr. broke up with Bessette because someone told him that she was a “user, partier, that she was out for fame and fortune.” One of Bessette’s friends told Beller, however, that Carolyn was not discouraged and that she knew that “this would not be the end. John was a prize, and Carolyn had her eye on the ball.”
Either way, the couple eventually agreed to get married. They ultimately wed on September 21, 1996, in a private ceremony on Cumberland Island off the coast of Georgia. But even though everything about the event seemed like a fairy tale, from the $40,000 wedding dress to the ceremony conducted by candlelight, it didn’t take long for the newlyweds to run into problems.
Trouble Arises For The Newlyweds
Rumors emerged that Bessette-Kennedy was using cocaine; both she and JFK Jr. were accused of having extramarital affairs. The truth is difficult to unravel, but it seems clear that Carolyn Bessette-Kennedy was struggling to adjust to the media scrutiny that her husband had known his entire life. And she didn’t know if she wanted to bring a child into such an environment.
“I hate living in a fishbowl,” Bessette-Kennedy told a confidante, according to The Kennedy Curse: Why Tragedy Has Haunted America’s First Family for 150 Years by Edward Klein. “John may be comfortable living like this, but I’m not. How could I bring a child into this kind of world?”
MediaPunch Inc/Alamy Stock PhotoJohn F. Kennedy Jr. and Carolyn Bessette-Kennedy reportedly had a strained marriage before their tragic deaths.
Meanwhile, JFK Jr. told one of his friends that whenever he brought up having children, his wife “turns away and refuses to have sex with me… It’s impossible to talk to Carolyn about anything. We’ve become total strangers. I’ve had it with her… It’s got to stop. Otherwise we’re headed for divorce.”
By mid-1999, the couple was allegedly living apart. But Carolyn Bessette-Kennedy agreed to attend a Kennedy family wedding with her husband that July. What’s more, she agreed to fly up in his plane, even though she’d reportedly expressed reservations about his flying abilities before.
How Carolyn Bessette-Kennedy And John F. Kennedy Jr. Died In A Tragic Plane Crash
On July 16, 1999, Carolyn Bessette-Kennedy met her husband and her sister Lauren at Essex County Airport in New Jersey. Though Bessette-Kennedy purportedly did not “trust” JFK Jr.’s piloting abilities, she had agreed to an arrangement by her sister, Lauren (who was reportedly hoping to help save the couple’s fractured marriage). JFK Jr. would fly Lauren to Martha’s Vineyard, and then he and Carolyn would continue on to Hyannis Port, Massachusetts, for the upcoming wedding of JFK Jr.’s cousin, Rory.
Lauren Bessette and JFK Jr. arrived at the airport around 6:30 p.m.; Carolyn Bessette-Kennedy arrived closer to 8 p.m. (Though rumors emerged that Bessette-Kennedy was delayed because of a long pedicure, Beller claims that there’s no truth to them.) Once Bessette-Kennedy arrived, the three of them boarded JFK Jr.’s single-engine Piper Saratoga II HP airplane and then took off at 8:38 p.m. for what should have been an easy flight.
FlugKerl2/Wikimedia CommonsAn aircraft similar to the one that JFK Jr. was flying when he crashed off the coast of Martha’s Vineyard in July 1999.
However, something went wrong during the flight. At 9:40 p.m., the plane started to plummet at an alarming speed, dropping from 2,500 feet to 1,800 feet in less than 30 seconds. The plane lost altitude at about 53 miles per hour, which was later deemed more of a “dive” than a “descent.”
That night, JFK Jr.’s plane crashed into the ocean off the coast of Martha’s Vineyard, where the Coast Guard discovered the wreck at a depth of about 110 feet on July 20th. On the next day, July 21st, the bodies of JFK Jr., Carolyn Bessette-Kennedy, and Lauren Bessette were recovered. They were found upside down and strapped into their seats, and they had all died upon impact. JFK Jr. died at age 38, Carolyn at 33, and Lauren at 34.
A National Transportation Safety Board (NTSB) investigation concluded in 2000 that the cause of the crash was “pilot error.” It found that JFK Jr., a relatively inexperienced pilot, had chosen to fly in hazy conditions without an instructor and had failed “to maintain control of the airplane during a descent over water at night, which was a result of spatial disorientation.”
National Transportation Safety BoardThe wreckage of JFK Jr.’s plane crash, which killed him, Carolyn Bessette-Kennedy, and Lauren Bessette.
In the aftermath, other theories about the crash emerged. They included that JFK Jr. had crashed the plane on purpose because of his ongoing problems with his marriage and his political magazine, that he’d been murdered, and even that he was still secretly alive somewhere. But ultimately, the crash was seen as just another tragedy to befall the Kennedy family.
Unfortunately, amidst that heartbreaking story, Carolyn Bessette-Kennedy and her sister Lauren are sometimes treated as footnotes.
The Murky Legacy Of Carolyn Bessette-Kennedy
After her death, a friend of Carolyn Bessette-Kennedy told The New York Times that she hadn’t missed the fashion world after her marriage because she had “plenty to do to adjust to being Mrs. John F. Kennedy Jr.” Indeed, that’s how Bessette-Kennedy is primarily remembered.
Her own story as an individual has often gotten lost over time.
But Bessette-Kennedy, who valued her privacy, was always difficult to know. Kennedy biographers like Edward Klein, who wrote The Kennedy Curse, described Bessette-Kennedy as a cocaine user who was unfaithful to her husband. Beller, in her 2024 book, portrays Bessette-Kennedy in a more positive light by describing her as empathetic, nurturing, and “a revelation.”
Even decades after her death, Carolyn Bessette-Kennedy continues to draw the eye — and inspire debates about her legacy. Her glamour, timeless style, and tragic story fits well within the Kennedy narrative. But any real truths about her were lost back in July 1999, when her husband’s plane went down.
After reading about the life and death of Carolyn Bessette-Kennedy, discover the forgotten story of Arabella Kennedy, John F. Kennedy and Jackie’s first daughter. Or, go inside the disturbing story of Rosemary Kennedy.
