The Heartbreaking Story Of Lauren Bessette, JFK Jr.’s Sister-In-Law Who Perished In His Plane Crash

Published December 30, 2024
Updated January 21, 2025

On July 16, 1999, 34-year-old Lauren Bessette boarded her brother-in-law's plane alongside her sister Carolyn for what was supposed to be a short trip to Martha's Vineyard — then their flight ended in tragedy.

Lauren Bessette

Greenwich High SchoolBy all accounts, Lauren Bessette was bright, adventurous, and caring.

On July 17, 1999, a beachcomber at Philbin Beach in Martha’s Vineyard came across an unusual find: a business card for a Morgan Stanley financial executive named Lauren Bessette. The name almost certainly rang a bell. Lauren’s sister, Carolyn Bessette-Kennedy, was married to John F. Kennedy Jr. But the card had washed up on the beach for a terrible reason.

The evening before, Lauren, Carolyn, and JFK Jr. had taken off from Essex County Airport in New Jersey in John F. Kennedy Jr.’s plane. JFK Jr. planned to first fly to Martha’s Vineyard, to drop off Lauren, and then continue to Hyannis Port, Massachusetts with his wife to attend a family wedding.

The flight, however, went horribly wrong. On the night of July 16th, it crashed into the ocean off the coast of Martha’s Vineyard — killing all three onboard.

In the decades since, the focus of the story has largely been John F. Kennedy Jr. and Carolyn Bessette-Kennedy. But what about Lauren? Though she’s often relegated to a footnote in history, she has a story all her own.

Lauren Bessette’s Sparkling Life In Hong Kong And New York City

Lauren Bessette And Carolyn Bessette

Bessette FamilyLauren Bessette and Carolyn Bessette.

Lauren Bessette and her twin sister Lisa were born on November 5, 1964 in White Plains, New York. Their younger sister Carolyn was born just 14 months later. The girls eventually moved to Old Greenwich, Connecticut, after their parents got divorced and their mother remarried.

After graduating from Greenwich High School in 1982, Lauren majored in economics at Hobart and William Smith Colleges, then briefly worked at Morgan Stanley before pursuing an MBA at the University of Pennsylvania’s Wharton School of Business. She graduated in 1991, then returned to Morgan Stanley. Lauren began working in the company’s Hong Kong office in 1994, and she did so well that she was promoted to vice president in 1996.

Lauren — fun-loving, brilliant, and fluent in Mandarin — struck her colleagues and friends as someone who was bright and adventurous. But it was her sister, Carolyn Bessette, who caught the attention of the world.

Lauren Bessette's Sister Carolyn

ZUMA Press, Inc./Alamy Stock PhotoCarolyn Bessette, Lauren Bessette’s younger sister — and JFK Jr.’s wife.

Back in the United States, Carolyn had started seeing John F. Kennedy Jr., the son of President John F. Kennedy and Jacqueline Kennedy Onassis. To outside observers, the glamorous couple seemed to enjoy a whirlwind courtship, which eventually led to a fairytale wedding in 1996.

But behind the scenes, things were fracturing. Rumors spread that Carolyn was using cocaine; both Carolyn and JFK Jr. allegedly had extramarital affairs. Carolyn struggled to adjust to the public scrutiny of being a Kennedy, and JFK Jr. was frustrated at her reluctance to have children.

By mid-1999, the couple were reportedly living apart.

Jfk Jr And Carolyn Bessette Kennedy

MediaPunch Inc/Alamy Stock PhotoJohn F. Kennedy Jr. and Carolyn Bessette-Kennedy were reportedly having issues in their marriage before their fatal flight.

Lauren Bessette, who had moved back to New York City in 1998, working in Morgan Stanley’s Manhattan offices, tried to be a peacemaker in the marriage. At a lunch at the Stanhope Hotel on July 14, 1999, Lauren encouraged Carolyn to accompany JFK Jr. to the wedding of his cousin, Rory, which was scheduled on July 17th at the Kennedy family compound at Hyannis Port. Fatefully, Lauren even offered to fly with them.

Carolyn agreed — and the plan was set. They would take JFK Jr.’s plane and fly Lauren to Martha’s Vineyard on July 16th, then continue on to Hyannis Port for the wedding. But they never made it to their planned destinations.

How John F. Kennedy Jr.’s Plane Crashed In 1999

Piper Airplane

FlugKerl2/Wikimedia CommonsA plane similar to the single-engine Piper Saratoga II HP airplane that JFK Jr., Carolyn Bessette-Kennedy, and Lauren Bessette flew in on July 16, 1999.

On July 16, 1999, Lauren Bessette, John F. Kennedy Jr., and Carolyn Bessette-Kennedy met at Essex County Airport in New Jersey. Lauren and JFK Jr. arrived around 6:30 p.m.; Carolyn arrived later, closer to 8 p.m.

JFK Jr. was purportedly in good spirits that day. The day before, he’d gotten a cast on his ankle removed (he was recovering from a paragliding accident). This meant he could walk more easily — albeit with a cane or crutches. And JFK Jr. loved to fly. Despite rumors that his wife had reservations about his flying hobby, JFK Jr. 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.”

Though JFK Jr. was considered something of a novice pilot, he declined an offer from one of his flight instructors to accompany him during the short flight from New Jersey to Martha’s Vineyard and Hyannis Port.

The trio boarded JFK Jr.’s single-engine Piper Saratoga II HP airplane and took off at 8:38 p.m. But about an hour into the flight, something went terribly wrong. The plane started to plummet, diving from 2,500 feet to 1,800 feet in less than 30 seconds. Not long after that, it crashed into the ocean.

Plane Crash That Killed Lauren Bessette

National Transportation Safety BoardThe wreckage from the plane crash that killed JFK Jr., Carolyn Bessette-Kennedy, and Lauren Bessette.

At Hyannis Port, JFK Jr.’s family grew concerned when he and Carolyn didn’t arrive as scheduled. They alerted the Coast Guard at Cape Cod to the situation at 2:15 a.m. on July 17th, and authorities soon began a search for the plane. But just hours later, some troubling debris washed up on the shore of Philbin Beach in Martha’s Vineyard: a headrest, a black canvas suitcase, and one of Lauren Bessette’s business cards.

On July 20th, the missing plane was located in the ocean at a depth of 110 feet off the coast of Martha’s Vineyard. The next day, the bodies of JFK Jr., Carolyn Bessette-Kennedy, and Lauren Bessette were discovered, still strapped to their seats. JFK Jr. died at 38, Carolyn at 33, and Lauren at 34.

They had all died upon impact.

As the tragic news spread across America, many headlines seemed to focus on the loss of JFK Jr. and his wife — as the plane crash appeared to be yet another example of the so-called Kennedy curse. That said, some headlines didn’t mention Carolyn at all. And hardly any focused on Lauren.

Lauren Bessette’s Forgotten Story

Newspaper Article About Jfk Jr's Death

Steve Skjold/Alamy Stock PhotoA copy of Newsweek mourning John F. Kennedy Jr.’s death. Lauren Bessette received far less attention.

In the aftermath of the tragedy, most of the world’s focus was on what had caused JFK Jr.’s plane crash. Despite ominous theories that JFK Jr. had crashed the plane on purpose to escape a failing marriage and his struggling magazine, George, or that he had been murdered for seeking the full story about his father’s assassination, a National Transportation Safety Board (NTSB) investigation determined that the cause of the crash was “pilot error.”

The investigation found that JFK Jr. had failed “to maintain control of the airplane during a descent over water at night, which was a result of spatial disorientation.” Later on, his lack of experience, foot injury, and decision to fly without an instructor were also considered as possible factors.

Still, it was JFK Jr. — and not the Bessette sisters — whose death received the most attention. He was seen not only as a beloved public figure, but as a possible heir to the Kennedy political dynasty. Even Carolyn, though also publicly mourned, was mostly seen through the lens of the Kennedy family.

This reality was not lost on those who knew and loved Lauren Bessette — and who wanted her name to be remembered as well.

“As a community, we need to show our support,” one of Lauren’s high school classmates, who came to pay his respects at Lauren’s funeral, remarked to The New York Times. “The Kennedys have more than enough support, and Carolyn was recognized through them. The focus hasn’t been equal, and this is a nice way to remember Lauren as an individual.”


After reading about Lauren Bessette, who died alongside her sister Carolyn and brother-in-law John F. Kennedy Jr., go inside the curious mystery of what happened to President John F. Kennedy’s brain. Or, go inside some of the most eyebrow-raising theories about who really killed JFK.

author
Kaleena Fraga
author
A staff writer for All That's Interesting, Kaleena Fraga has also had her work featured in The Washington Post and Gastro Obscura, and she published a book on the Seattle food scene for the Eat Like A Local series. She graduated from Oberlin College, where she earned a dual degree in American History and French.
editor
Jaclyn Anglis
editor
Jaclyn is the senior managing editor at All That's Interesting. She holds a Master's degree in journalism from the City University of New York and a Bachelor's degree in English writing and history (double major) from DePauw University. She is interested in American history, true crime, modern history, pop culture, and science.
Citation copied
COPY
Cite This Article
Fraga, Kaleena. "The Heartbreaking Story Of Lauren Bessette, JFK Jr.’s Sister-In-Law Who Perished In His Plane Crash." AllThatsInteresting.com, December 30, 2024, https://allthatsinteresting.com/lauren-bessette. Accessed February 4, 2025.