Episode 17: John F. Kennedy Jr. Plane Crash

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What do you get when you combine a successful member of a famous family, a novice pilot, a stressful career, and relationship woes? In this episode of Take to the Sky: The Air Disaster Podcast, Shelly takes us through the story of the plane crash that claimed the lives of John F. Kennedy Jr., his wife Carolyn, and her sister Lauren. What should have been a quick flight in a private plane turned into a devastating loss for one of the USA's most famous families- but what caused the fatal crash? You might be surprised by some of the reasons things went wrong—both inside and outside of the cockpit!

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John F. Kennedy Jr. is Born into Famous Kennedy Family

It is the year 1999. Everyone was having a meltdown about Y2K ruining computers. PayPal was called one of the worst business ideas of the year. DVD players were just starting to edge out VHS players. And the Euro was first introduced. And, also, in 1999, John F. Kennedy Jr. and his wife Carolyn Bessette-Kennedy are a global media obsession. 

John was born on November 25, 1960 to the newly elected President John F. Kennedy and his wife, Jacqueline Bouvier Kennedy. And being a Kennedy, especially in the 1960s, meant being a part of a family that was equally famous and infamous. 

The Kennedys are a large, Irish Catholic family, headed up by Joseph P. Kennedy, who was a former bootlegger and failed diplomat. The President’s older brother, Joe Jr., died a war hero. And when that happened, all of Joe Sr.’s aspirations of having a Kennedy in the White House fell to John Sr. (referred to here as “JFK”). And when JKF was elected President in 1961, he asked his brother Bobby to join his Cabinet as Attorney General. The Kennedys seemed, on the outside, to be an ideal American family: young, stylish, charismatic, and powerful. 

The Kennedys Endure as Icons Through Assassination Tragedy

The world sees pictures of John Jr. as he grows up over the next two years in the White House, waiting for JFK to disembark Air Force One, running into his father’s arms and giving him hugs and kisses, and playing underneath the Resolute Desk in the Oval Office. Many Americans feel like they know John through these pictures, and he is nicknamed by the press as “John-John.” Though his family apparently never used that nickname with him.

And then, of course, in November of 1963, President Kennedy is assassinated while traveling in a motorcade in Dallas, TX. This event makes world news and shakes the American public to its core. It is just one of the many untimely Kennedy deaths the public will come to witness throughout time. The many untimely tragedies that impact the family become known as the supposed “Kennedy curse”.

One the most iconic pictures taken of John Jr. – and perhaps one of the most iconic photos of the 20th century – show three-year-old John saluting his father’s casket in 1963. This image made him an absolute media obsession all around the world. 

John F. Kennedy Jr. Grows Up Amidst Intense Media Coverage

As he grows up, John is hounded by photographers. But he learns to tolerate the constant media attention, and even in some instances, demonstrates some real grace under pressure. 

With that attention came the pressure of being someone the world wanted John to be versus who he wanted to be. The world had essentially transferred the expectations and love for JFK to John – whether he wanted it or not. He is often pictured in tabloids on the arm of this actress or that actress, and one headline even made fun of his failure to pass the NY state bar exam with the headline, “The Hunk Flunks.” Eventually, of course, John passes the bar on the 3rd try and works for several years as prosecutor in the Manhattan District Attorney’s office. 

According to close friends, he never wanted to be famous for just being famous – he wanted to be known for accomplishing something of his own. He wanted to be a person of substance. 

Before he could settle the question around what that might mean for him, tragedy strikes yet again, when John’s mother, the former First Lady Jacqueline Kennedy, dies of cancer in May of 1994. This is just 4 months after her diagnosis. Which is also when his cousin, Anthony Radziwill, who is also his best friend and like a brother to him, discovers that he, too, has terminal cancer. 

When Jackie dies, John shows a stoic public face, but to his friends, her death has a huge impact on him. He is shocked at how quickly the cancer consumed her. John realized, through his own losses, whatever you had, you could lose in a second. This drives him to set out to make his own mark on the world. 

John F. Kennedy Jr. Creates First Political Magazine, George

In the late 90s, politics was migrating into popular culture in a way it hadn’t before. With the presidency of Bill Clinton, which, like him or hate him, brought a youthful vibe to politics. Some media pundits even said Clinton captured the public’s imagination the same way JFK had in the 1960s. As a result, there was a lot of voting campaigns that specifically targeted youth, such as MTV’s Rock the Vote campaign. 

Reading the current climate converging around culture and politics, John gets the idea for his own magazine, George, with his partner Michael Berman, who helps John find investors to boost the project. 

In creating George, John was driven by a passion for destroying the bipartisanship of politics. During his inaugural press conference for the debut of the magazine in 1995, which was held very intentionally at Federal Hall in New York City, he said, “We want to make a magazine uncolored by a single partisan point of view.”

And initially, the magazine is a success. The first issue sold out its entire 500,000 copies. Yet, with everything else John endeavored to do, the magazine was clouded by extremely high expectations and a lot of skepticism. Many in the press want to know if John’s political magazine project is really a step toward politics. While John seems ambivalent with the press about his desire to enter politics, those close to him said that he indeed always thought politics would be his final destination. 

JFK, Jr. Marries Carolyn Bessette 

In 1996, John marries Carolyn Bessette, a former model and publicist for Calvin Klein. She has two older twin sisters, Lauren and Lisa. Carolyn met John in 1994, when they began dating. Everyone close to John said they could tell immediately that he was madly in love with Carolyn and that they felt strongly he thought she was “the one”. They wed in an ultra-secretive ceremony on Cumberland Island in a remote part of Georgia on September 21, 1996. 

George Magazine Plagued by Challenges

On the surface, things look good for John. But his life was anything but storybook perfect. 

First, despite its initial success, George the magazine is now struggling as sales are down by one-third. The first misstep that leads them down the path of decline comes two years prior in 1997, when John was supposed to interview Fidel Castro in commemoration of the Bay of Pigs event from 1962. But when he got to Cuba for the interview, Castro refused to be interviewed and basically gave a six-hour monologue on American imperialism. 

When John returned to the magazine empty handed, his business partners went crazy because they had sold ad space in anticipation of this high-profile interview by John with his father’s political archnemesis, Castro. Soon after, advertisers start pulling out. And the next big misstep was when John and his staff chose not to cover the Clinton impeachment trial in 1998, which was perceived as showing a bias toward wanting to protect the President, a sentiment that went against was George was supposed to stand for in the industry. 

Over the next couple of years, the magazine gets thinner and thinner with less advertisers. In 1999, there is now huge pressure on John to identify a turnaround strategy before investors pull out. The magazine’s publisher has asked John to create a business plan for turning it around, which includes a digital strategy that John wanted to pursue as the future of George. 

Intense Media Coverage of Carolyn Bessette Adds to Mounting Pressure

Second, John and Carolyn are rumored to be having marital difficulties. One of the key challenges is the intense media scrutiny on Carolyn. While being in the spotlight was familiar to and even tolerated by John, Carolyn was reportedly deeply distrustful and resentful of the media attention that their presence garnered. Friends think John might have underestimated how strong the interest in Carolyn would be before they wed and what impact that would have on her. There was a sense that those in media did not think she was good enough for John, and because of that unkind and unfair sentiment, she quickly garnered a reputation of being “difficult” and “emotional”. And friends being interviewed for the A&E documentary say that this created tension in their marriage as Carolyn took out her anger on John, and John didn’t understand her anger. In February 1999, they decide to seek couples therapy.

JFK Jr.’s Closest Friend and Cousin Battles Terminal Cancer

Third, John is dealing with the impending death of his cousin Anthony, who was diagnosed with a rare sarcoma in 1994. It’s actually a miracle he’s still living in 1999. Carole, Anthony’s wife, said that John just refused to believe that Anthony would die. John steps in and gets him the best doctors and the best treatment, thinking he can solve this problem. But sarcoma is a very rare cancer and clinical trials are not helping Anthony’s tumors reduce in size. John reportedly told his chief of staff, Rosemary Terenzio, “I don’t know if I can get through this.” Anthony was the one person in the world that knew all of John’s secrets and he knew Anthony’s. They were like brothers. John was deeply burdened by the fact that he did not know how he was going to survive this loss. And to him, he feared this loss would be the one that might finally break him. 

Day of Crash: Kennedy, Wife, and Sister-in-Law Depart for Martha’s Vineyard

These are the things happening in John’s life when, on July 16, 1999, he arrives at Essex County Airport in New Jersey. This airport is known to the many wealthy Americans who have private planes there, and it’s only an hour from Manhattan, which made it a convenient choice for John and his passengers, which include his wife Carolyn and her sister, Lauren. 

Lauren makes the brief walk over from her office, and she and John climb into John's white Hyundai convertible to make the drive out to New Jersey's Essex County Airport. It’s a Friday, and the normally 40-minute trip takes an hour-and-a-half with rush hour traffic clogging the roads. They arrive at the airport around 6:30 PM. 

The plan for the flight is straightforward: John will drop Lauren off in Martha’s Vineyard while he and Carolyn continue by air onto Hyannis Port where they will stay at the Kennedy family’s compound to attend the wedding of his cousin, Rory Kennedy, to Mark Bailey. 

His plane is a Piper Saratoga. He reportedly bought his first plane, which was not this one, because he hated flying commercial because of the press at the airports. And of course, he loves the freedom that flying brings. As a pilot, John is certified to fly under visual flight rules, or VFR, which means he will fly using the natural horizon and visual cues. 

While Lauren is already there at the airport with John, Carolyn is not. John inquires where she is, and he soon discovers that she took a last-minute shopping trip in the city. It being a Friday evening, John is immediately frustrated because now he knows they are going to arrive even later. They were supposed to depart while there was plenty of daylight left. When Carolyn arrives two hours later, around 8:30 PM, it is already starting to get dark.  

JFK, Jr.’s Plane Goes Missing, Search Initiated

John immediately begins his pre-flight checks, and then at around 8:48 PM, the plane departs and quickly gets to cruising altitude, which for a plane of this size is 5,500 feet. At around 9 PM, the Kennedy plane leaves the mainland coast behind as it starts to fly out across water toward Martha’s Vineyard.

By 10 PM that night, air traffic control (ATC) from Martha’s Vineyard has had no contact with the plane. While it was not unusual for flights to be overdue, hours passed, and then, by early morning, their families as well as ATC accept the chilling truth: John, Carolyn, and Lauren are missing.

At around 3 AM on July 17, the Federal Aviation Administration (FAA) calls the Coast Guard to initiate a search at sea for the missing plane. When the Coast Guard begins their search, they have a heightened hope of finding all three still alive. 

Soon, the local military and law enforcement join the search, which is massive and highly unusual in scope for a typical missing small plane. And even private citizens come out with their small boats to help in the search. But of course, this is the son of an assassinated president, which means that everyone is paying extra close attention. Later, President Clinton, the FAA, and Coast Guard receive criticism for the special treatment that the missing Kennedy plane received from rescuers. In fact, the Coast Guard at one point wanted to call off the search and President Clinton told them, according to his own words, to get back out there at it and they would find them. 

Meanwhile, the public is stunned at hearing that John’s plane is missing. Many remain hopeful that somehow, against all odds, they will be found alive. No one can seem to believe that this would happen to them – the unfairness of it really struck the public’s imagination. 

But the next day, searchers find debris off the coast of Martha’s Vineyard, including part of a nose wheel, seat cushions, and one suitcase. Upon identifying the debris as belonging to John’s plane, the search soon shifts from rescue to recovery. 

The American public is yet again horrified and transfixed at the most current Kennedy tragedy: John F. Kennedy Jr. is likely dead. 

NTSB Investigates Cause of Kennedy Plane Disaster

The NTSB commences their investigation while the plane is still missing and are treating it as a fatal air accident almost from the start. Immediately, given that it is John Kennedy’s plane, investigators are concerned it may be a deliberate criminal act. FBI shared with NTSB that John Jr. has been the target of three kidnapping threats, the latest one just 4 years earlier. Investigators need to consider, was this plane shot down, or did it get bombed?

Since John did not file a flight plan, the FAA must look at the radar system to see where the plane traveled because small planes of this size, when flying under visual flight rules, are not required to file flight plans. 

When the FAA examines the radar data, here is what they find: John’s plane is flying in line with the coast, and then it starts to fly toward Martha’s Vineyard. Then suddenly, it starts to fly away from Martha’s Vineyard, which is odd since that was their first stop. About 30 miles outside of Martha’s Vineyard, the plane makes a series of baffling maneuvers. First, it descends, next it turns right and climbs again, then it’s level for one minute before it makes a sudden left and right turn, followed by a steep dive, plunging about 100 feet per second toward the ocean. For obvious reasons, the NTSB think this is a highly unusual pattern.

John F. Kennedy Jr., Wife, and Sister-in-Law Perish in Plane Crash

Four days after the plane goes missing, the Navy locates the wreckage of the Piper Saratoga with all three bodies onboard, still strapped into their seats. The plane was found only at a depth of 120 feet beneath water. 

And then on the morning of July 22, John and Carolyn’s ashes are scattered at sea from the Navy destroyer USS Briscoe off the coast of Martha's Vineyard. A memorial service was held for Kennedy on July 23, 1999, at the Church of St. Thomas More, which was a parish that Kennedy had often attended with his mother and sister. The invitation-only service was attended by hundreds of mourners, including President Bill Clinton, who presented the family with photo albums of John and Carolyn on their visit to the White House from the previous year. 

Eventually, 75% of the Piper Saratoga is recovered from the sea floor. The NTSB’s first task is to determine if the plane hit the water intact or if it broke apart in midair. After studying the reassembled wreckage in a hangar and studying the images of how the plane rested on the sea floor, they realize the plane hit the water intact. They also locate all four corners of the plane, which we as know from so many other investigations, is a key indicator of this fact as well. 

The media is now in overdrive and the NTSB admittedly feels the crushing pressure placed on them to investigate and find out what has stolen America’s prince. And to make matters worse, the paparazzi are paying good money to anyone who has images of the crashed plane, so investigators take extra security precautions in securing the underwater image from the crash scene. 

NTSB Rules Out Mechanical Causes of John F. Kennedy Jr. Plane Crash

Since small planes like John’s plane are not required to carry recorders (the so-called black boxes), the NTSB examines the wreckage and tries to deduce what happened based on the way each piece has or has not been damaged. They observe that the right wing is more damaged than the left wing and it has this accordion-type crush pattern, indicating that the right wing hit the water first. And the roof is also badly damaged while the floor is not. This evidence gives them an idea of what the angle of impact might have been – that the plane banked right and then hit the water almost upside down. Investigators now know HOW they hit the water, but not WHY. 

The NTSB first wants to know, was this crash caused by anything mechanical or technical? They look at engine failure as a potential culprit, which would explain the strange maneuvers the plane was making right before it crashed – if the single engine lost power, then that would detriment the flight controls. When they examine the engine, they see the propeller blades were bent in a way that indicates the engine was working when the plane went into the sea. Engine failure is the not the cause. 

Next, they look at the system controls and the complicated cable system that helps the pilot operate and steer the plane in-flight. When they separate all the cables and lay them out, they find that none of the cables snapped prior to impact; the only damage that exists is the standard damage that happens during the impact of a crash. Investigators also check the attitude indicator, which if that were malfunctioning, would have given the pilot a false sense of direction and of what was level. But this, too, seemed to be working effectively all the way up until the moment of impact.  

NTSB Investigates Pilot Error as Possible Cause of JFK Jr. Plane Crash

This leaves them with the final factor: the pilot. 

NTSB must identify what caused this human performance error. To understand that, they must understand what John’s mental state was at the time of the flight, and so they retrace everything he did over the final 3-4 days of his life. 

On July 16th, John was still on crutches, having had surgery on his ankle after a glider accident, and on this day, he had gone to the doctor to have the cast removed and have a boot placed on his foot. Pilots need both hands and feet to fly since the rudder is controlled by the feet. But when investigators look at x-rays of John’s ankle, they see it was indeed healed and strong enough for him to fly with the boot on. 

The NTSB next hears of rumors that John and Carolyn’s marriage hit a rocky patch. Investigators explore if this fact was placing a strain on John, and if so, was it so much so that it may cause him to be distracted. Again, Carolyn has a reputation for being demanding and difficult, although, close friends say that she was strong-willed and did not treat John with kid gloves. And John allegedly really loved that about her, but this same behavior also created friction in the marriage. And lastly, is the precarious financial situation of his newspaper, George, which was in jeopardy of losing its funding unless he could come up with a business plan for switching to digital. 

Taking all of that into consideration, investigators wonder, was there also the added pressure of flying your own plane? When looking at John’s record, they find he has just about 300 flight hours, which means he is not a total rookie but he’s still learning. John had taken lessons on and off for the better part of 17 years, but had little experience flying on his own. His solo time in the cockpit equaled only about 70-75 hours. And, during these 17 years of flight instruction, he also had about 11 different instructors. The NTSB finds this is highly unusual – most people who learn to fly stick to one instructor, especially during the instrument rating portion of the training. 

But John was no ordinary student: as a Kennedy, he is what his friends described as “chronically busy”. That meant he would take a lesson whenever and wherever he could with whomever was available so he could work it around his very busy schedule. This raises questions around the quality of the instruction and how much learning transfer actually occurred. 

Investigators next discover that on the day of the crash, his primary instructor offered to fly with him, but John said no thanks. The instructor said he had this feeling that John really wanted to do it himself. 

John was only qualified to fly using VFR. He had started to work toward his instrument rating but had not completed it. That’s the harder thing to do, because it involves using only instruments to fly instead of looking outside the aircraft, especially while flying over open water at night, like he did that night.

Investigators wonder why John had chosen to fly into the weather on the night of the crash with it being so foggy. They found he checked the weather at 6:34 PM when he first got to the airport. But Carolyn’s last-minute shopping trip set them back two hours. The weather had deteriorated by then. There was a significant haze over the horizon and visibility was especially bad under 6,000 feet, and John was flying around 5,500 feet. These are certainly conditions that would be too dark and hazy for someone only flying on VFR. 

They check his radio on the plane to see what frequency he was dialed into, if any, for weather updates, and NTSB finds that his input was off by one number, so he was not getting updates as he would needed to have gotten on the weather inflight or before he started out. 

John F. Kennedy Jr. Became Disoriented, Lost Control of Aircraft

To the NTSB, a chilling conclusion is taking shape. This is the story of a man in over his head, personally and as a pilot. 

Investigators deduce what happened on the flight: with these hazy conditions, he would have no way to tell which way was up or down. Instead of following the coastline, he has to shift out onto the water to make it to Martha’s Vineyard. Visibility is getting worse as they continue to fly, and this is when he starts to descend over the water, getting closer to Martha’s Vineyard. Now, all that visual reference is gone – there are no lights or any other distinguishing features from the coast to help navigate.

The NTSB deduce John may have tried to check the weather again, but since the radio was on the wrong frequency, he may have looked away for a while, trying to figure out why the frequency wasn’t making any sound. And while that happens, he slips into that first bank. 

What happens next is fatal: spatial disorientation. Basically, this happens when a pilot’s perception of direction does not agree with reality. It usually happens when flying into poor weather conditions with low or no visibility. Under these conditions the pilot may be deprived of an external visual horizon, which is critical to maintaining a correct sense of up and down while flying.

According to Aviation Accidents.net, approximately 80% of the private pilots in the United States do not have an instrument rating, and therefore are prohibited from flying in conditions where instrument skills are required. Not all pilots abide by this rule and approximately 40% of the NTSB fatal general aviation accident reports list continuation of flight into conditions for which the pilot was not qualified as a cause.

In this scenario, with John, maybe he looks back from his radio to his instruments – they are telling him he is banking, but his mind, disoriented, tells him another thing. It is in this moment that John would have had to have disregarded what his brain told him and only go with his instruments. And because of his lack of experience, he likely didn’t trust his instruments. He tries to make corrections, but they don’t line up with his artificial horizon. And so, he makes the wrong turn,  and all of a sudden, he is in a steep dive that will cost him, his wife, and his sister in law their lives. 

The Legacy of John F. Kennedy Jr.

During the public memorial service for John, his paternal uncle, Ted, stated: “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.”

There is obviously not a memorial related to this crash, but on September 19, 2003, the ARCO Forum at Harvard University's Kennedy School of Government was renamed to the John F. Kennedy Jr. Forum of Public Affairs. An active participant in Forum events, John had been a member of the Senior Advisory Committee of Harvard's Institute of Politics for fifteen years.

JFK Jr. Death and the So-Called Kennedy Curse

Obviously, this is a major loss to the Kennedy family who have seen so many others pass on early. In fact, John and JFK are only a few of the Kennedys to have suffered an untimely death. 12 Kennedys since 1944 have died in accidents, suicide, or from being killed (murder and from war). And interestingly enough, several members in addition to John Jr. have been involved in plane crashes: JFK’s sister Kathleen (John’s aunt) perished in a plane crash in 1948; in 1955, Ethel Kennedy, who married Robert Kennedy Sr., lost both her parents in a plane crash in Oklahoma; and in 1964, Senator Ted Kennedy was injured in a plane crash that killed one of his aides and the pilot. 

Despite the celebrity and the Kennedy tragedy surrounding John’s death, this crash brings a lot of visibility to the dangers of spatial disorientation. 

And, we cannot forget the Bessette family who lost not one but two daughters in this crash. Ann Freeman, Carolyn’s mother, sued within a year of the crash. In a public statement on the one-year anniversary, she said, “The loss of these three young people whom we loved very much has forever changed our lives. We continue to struggle with our grief.” The Kennedy and Bessette families negotiated to reach a settlement. While the final amount was undisclosed, sources say it is close to $15 million. 

And THAT is the story of the crash that killed John F. Kennedy Jr., Carolyn Bessette Kennedy, and Lauren Bessette.

Show Notes:

Shelly and Stephanie shared a few memorable disaster stories from previous trips—and we want to hear yours! Send us your travel tales of woe through our contact form or social media channels. We'll share a few during upcoming podcast episodes!


Written and produced by: Shelly Price and Stephanie Hubka
Directed and engineered by: Crosse deStreit, Salmon Pond Studios
Sound editing by: Stephanie Hubka
Graphic design and website by: Adam Hubka
Music by: Mike Dunn
John F. Kennedy Jr. Plane Crash

Reconstructed plane from the John F. Kennedy Jr. crash. Image Source: Alethonews.com

John F. Kennedy Jr. Plane Crash

John F. Kennedy Jr.'s aircraft, a 1995 Piper Saratoga. Image Source: Boston Globe

John F. Kennedy Jr. Plane Crash

Rescuers searching for the aircraft and passengers. Image Source: Reuters

John F. Kennedy Jr. Plane Crash

Flowers outside of a makeshift shrine honoring John F. Kennedy Jr., his wife Carolyn, and his sister-in-law Lauren. Image Source: Reuters