How A Sudden Plane Crash Ended The Lives Of JFK Jr., His Wife, And His Sister-In-Law

Published July 10, 2024
Updated January 8, 2025

One of the Kennedy family's most heartbreaking tragedies, John F. Kennedy Jr., his wife Carolyn Bessette-Kennedy, and his sister-in-law Lauren Bessette died in a plane accident on July 16, 1999.

Jfk Jr Plane Crash

dpa picture alliance/Alamy Stock Photo JFK Jr.’s plane crash took place in July 1999, just months after this photo was taken.

John F. Kennedy Jr. captivated the world for much of his life, but two moments stand out in particular. The first was when he saluted his father’s coffin at age three after the Kennedy assassination. The second was almost 36 years later — the tragic moment of JFK Jr.’s plane crash.

On that day, July 16, 1999, JFK Jr. took off from Essex County Airport in New Jersey alongside his wife, Carolyn Bessette-Kennedy, and his sister-in-law, Lauren Bessette, in his single-engine Piper Saratoga II HP airplane. JFK Jr. planned to drop Lauren off at Martha’s Vineyard and then continue on to Hyannis Port, Massachusetts with his wife for a family wedding.

But they never made it. When JFK Jr., his wife, and his sister-in-law failed to arrive at their destinations, their family members launched a five-day search that reached a heartbreaking end. On July 21st, the bodies of JFK Jr., Carolyn, and Lauren were discovered off the coast of Martha’s Vineyard.

So what happened on the day of JFK Jr.’s plane crash?

JFK Jr.’s Final Days Alive

By July 1999, 38-year-old John F. Kennedy Jr. seemed to have the entire world at his fingertips. The son of President John F. Kennedy and Jacqueline Kennedy, JFK Jr. had a beautiful wife, 33-year-old Carolyn, and he was the editor-in-chief of a glossy political magazine he’d started, George.

Jfk Jr And Carolyn Bessette Kennedy

MediaPunch Inc/Alamy Stock PhotoJohn F. Kennedy Jr. and his wife, Carolyn Bessette-Kennedy, after the White House Correspondents’ Dinner in Washington, D.C. on May 1, 1999 — just months before JFK Jr.’s plane crash and the couple’s untimely deaths.

But things weren’t as picture-perfect as they seemed. For starters, George was struggling. According to the book The Kennedy Curse: Why Tragedy Has Haunted America’s First Family for 150 Years by Edward Klein, George was expected to lose $10 million in 1999. And the time that JFK Jr. spent tending to the floundering magazine was just one of his alleged marital problems.

In the months before JFK Jr.’s plane crash, rumors abounded about his marriage to Carolyn. After their wedding in 1996, Carolyn, a former Calvin Klein publicist, reportedly struggled to handle JFK Jr.’s level of fame. She was hounded by paparazzi, and felt trapped in the couple’s New York apartment.

What’s more, the two disagreed over the matter of having children. JFK Jr. wanted them; Carolyn wasn’t as sure. According to Klein’s book, Carolyn told a friend: “I hate living in a fishbowl. John may be comfortable living like this, but I’m not. How could I bring a child into this kind of world?”

Meanwhile, Klein wrote that JFK Jr. complained to a friend that whenever he brought up children, Carolyn “turns away and refuses to have sex with me.” JFK Jr.’s frustration over the matter was such that he added: “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 July 1999, the two were reportedly living apart.

Jfk Jr's Death

Tyler Mallory/LiaisonJFK Jr. and Carolyn Bessette-Kennedy in happier times.

But then, Carolyn’s sister Lauren stepped into the marital fray. She invited JFK Jr. and Carolyn to lunch at the Stanhope Hotel on July 14, 1999. There, she encouraged Carolyn to accompany JFK Jr. to the wedding of his cousin Rory in Hyannis Port on July 17th. Lauren even offered to fly with them.

They planned to fly up just two days later, on July 16th. Sadly, all three would meet their deaths during JFK Jr.’s plane crash that very day.

Inside JFK Jr.’s Plane Crash In July 1999

On the day of JFK Jr.’s plane crash, JFK Jr. seemed to be in high spirits. The day before, he’d had an ankle cast removed. Though he was still in recovery from the broken bone (from a paragliding accident), it meant he could walk with a cane or crutches — and that he felt confident he wouldn’t need a co-pilot on his plane. He spent the day at the George office before making a quick trip to the gym. Then, JFK Jr. headed to the airport.

He and Lauren both arrived at Essex County Airport in New Jersey at around 6:30 p.m.; Carolyn arrived a bit later, at around 8 p.m.

Piper Airplane

FlugKerl2/Wikimedia CommonsAn aircraft similar to the single-engine Piper Saratoga II HP airplane that JFK Jr. flew on the day of his tragic death.

At the time, JFK Jr. was still something of a novice pilot. Though he’d earned his pilot’s license about a year earlier — and he had 300 hours of flying experience — JFK Jr. was still short of getting his instrument-rating certification. After JFK Jr.’s fatal plane crash, experts noted that this meant that he might have been an overconfident pilot.

Indeed, Carolyn reportedly lacked confidence in her husband’s piloting abilities, did not want to fly with him without an instructor present, and even allegedly said that she didn’t “trust” her husband when it came to flying. However, John F. Kennedy Jr. denied that she had any reservations, once remarking that she looked forward to flying just “as much as I do.”

In any case, Carolyn boarded JFK Jr.’s single-engine Piper Saratoga II HP airplane at Essex County Airport. The trio took off at 8:38 p.m.

By 9:26 p.m., the plane had reached Westerly, Rhode Island. But the aircraft failed to arrive at the Martha’s Vineyard airport as planned. Just 62 minutes into the flight, JFK Jr., Carolyn, and Lauren disappeared.

“There Is Always Hope”: Inside The Tragic Search For The Missing Plane

According to a timeline compiled by The Washington Post in the aftermath of JFK Jr.’s plane crash, the Kennedy family notified the Coast Guard at Cape Cod at around 2:15 a.m. that JFK Jr., Carolyn, and Lauren had failed to arrive. At about 4 a.m., the Coast Guard began to search for them.

That afternoon, debris from the plane washed up on Philbin Beach in Martha’s Vineyard. The debris included a headrest, a black canvas suitcase, and one of Lauren Bessette’s business cards.

“There is always hope,” Coast Guard Lt. Gary Jones told The Washington Post after the discovery. “But unfortunately, when you find certain pieces of evidence, you have to be prepared for anything.”

Coast Guard Answering Questions

USCGRichard M. Larrabee of the U.S. Coast Guard answers questions about JFK Jr.’s plane crash.

The next day, July 18th, more debris from the plane washed up on shore. By July 20th, the Coast Guard was able to locate the fuselage from JFK Jr.’s plane on the ocean floor at a depth of more than 110 feet. And on July 21st, the bodies of JFK Jr., Carolyn, and Lauren were recovered from the plane.

The three were found upside down and strapped into their seats. An autopsy later revealed that they’d died upon impact during JFK Jr.’s plane crash. At the time of their deaths, JFK Jr. was 38, Carolyn was 33, and Lauren was 34.

At JFK Jr.’s memorial service on July 23rd, his uncle Ted Kennedy eulogized him: “We dared to think, in that other Irish phrase, that this John Kennedy would live to comb gray hair, with his beloved Carolyn by his side. But like his father, he had every gift but length of years.”

The JFK Jr. plane crash was yet another tragedy for the Kennedy family, which had led to three untimely deaths. So what caused it?

The Debated Cause Of JFK Jr.’s Plane Crash

Jfk Jr's Plane Crash Wreckage

National Transportation Safety BoardThe wreckage from JFK Jr.’s plane crash, which caused the deaths of JFK Jr., his wife, and his sister-in-law.

The undisputed facts of the JFK Jr. plane crash are as follows: 14 minutes after the plane reached an altitude of 5,600 feet, it began to rapidly descend. At 9:40 p.m., the aircraft was at 2,500 feet. Shockingly, in less than 30 seconds, the plane dropped 700 feet — to 1,800 feet.

The plane was losing altitude at the equivalent of 53 miles per hour, a rate that was more like a “dive” than a “descent,” according to The Washington Post, and one that any pilot would struggle to recover from.

He did not make a distress call — so this all must have happened quickly.

So why did the aircraft descend so rapidly and crash? In 2000, the National Transportation Safety Board (NTSB) concluded that JFK Jr.’s plane crash was caused by “pilot error.” It stated that JFK Jr. was an inexperienced pilot who was unprepared for the conditions on the day of his death.

Though there were no weather warnings at the time, The Washington Post reported in 1999 that several pilots had reported unfavorable conditions over Long Island Sound and that “the in-flight visibility over the water was significantly reduced.” A pilot named Kyle Bailey — one of the last people to see JFK Jr. alive at Essex County Airport — told The New York Post that he’d canceled his own flight that evening out of concerns about the “hazy” sky. “It was a little bit hazy for me to fly over water,” Bailey recalled. “You can have a really clear day, and then the fog just rolls in in a matter of minutes.”

Ultimately, the NTSB report concluded that the crash was caused by the pilot’s “failure to maintain control of the airplane during a descent over water at night, which was a result of spatial disorientation.” JFK Jr. didn’t have enough experience to handle a solo flight on a “hazy” night, and he apparently became hopelessly disoriented in the dark and mist.

However, there are also darker theories about the cause of JFK Jr.’s death.

Tribute To Jfk Jr

John Mathew Smith & www.celebrity-photos.com/Wikimedia CommonsA tribute to JFK Jr. and Carolyn Bessette-Kennedy after their untimely deaths.

One suggests that JFK Jr. crashed the plane on purpose — that, faced with a crumbling marriage and a struggling magazine, he decided to end his own life. This theory states that the JFK Jr. plane crash was actually a murder-suicide. However, friends close to the couple deny this, stating that any marital strife would have been smoothed out eventually.

“Had he not crashed the plane, it would have been a meaningless few weeks of tension,” one told PEOPLE. “But it took on a life of its own because it was the last chapter of their life. One week they could have been at war, and the the next week they could be right back in love — we’ll never know.”

Another theory claims that JFK Jr. was murdered — possibly for seeking answers about his father’s assassination. And yet another theory states that he did not die at all, but is still alive somewhere to this day.

But while many of these theories have no evidence to support them, there is a lot we’ll never know about JFK Jr. What would he have done if he’d lived? Would he have continued to focus on his magazine? Or would he have entered the world of politics? Some believe that he would have eventually followed in his famous father’s footsteps, and run for president himself.

Sadly, we’ll never know what JFK Jr., Carolyn, or Lauren would have accomplished in their lives. On that hazy July evening in 1999, they perished in what experts called a “graveyard spiral.” It was another tragedy for the Kennedy family — and the Bessette family as well.


After reading about JFK Jr.’s plane crash, go inside some of the most convincing theories about who killed JFK — if it wasn’t Lee Harvey Oswald. Or, discover the tragic stories of Arabella Kennedy, JFK’s stillborn daughter, and Rosemary Kennedy, JFK’s forcibly lobotomized sister.

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.
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Fraga, Kaleena. "How A Sudden Plane Crash Ended The Lives Of JFK Jr., His Wife, And His Sister-In-Law." AllThatsInteresting.com, July 10, 2024, https://allthatsinteresting.com/jfk-jr-plane-crash. Accessed January 31, 2025.