Why Carolyn Bessette's Family Sued The Kennedy Family After Her Death

It is almost impossible to hear the name "Kennedy" and not to think of the popular Democratic president whose assassination in 1963 shook the world. The images of the famous Zapruder film, show John F. Kennedy and his wife Jacqueline traveling in an armed motorcade through the streets of Dallas, Texas, before the president is shot to death in broad daylight. But the assassination of JFK was only the most prominent of the many tragedies to befall the Kennedy family. Two of JFK's brothers also died in tragic circumstances, as did his son, the lawyer, journalist, and socialite John F. Kennedy Jr., a beloved figure in New York society who died when a plane he was piloting crashed into the Atlantic Ocean not far from Martha's Vinyard, Massachusetts, after taking off in poor conditions.

On board the flight were two passengers alongside Kennedy Jr.: his wife, the fashion publicist Carolyn Bessette, and Carolyn's sister, Lauren Bessette, who also perished in the crash. Their loss was devastating for both families, with the Kennedys releasing a public statement describing the pain they felt. However, tensions emerged in the years that followed concerning who exactly was at fault for the crash, leading to a high-profile legal battle in which the Bessettes sued the presidential family for wrongful death.

On July 16, 1999, John F. Kennedy Jr.'s plane took to the air from a runway in Essex County, New Jersey, en route to Martha's Vinyard, where he was due to drop off his sister-in-law before he and his wife Carolyn took off again to Cape Cod, where they were planning to attend a wedding. The aircraft was a Piper Saratoga, a light aircraft that Kennedy Jr., who had just 300 hours of flight experience under his belt, would steer by eye having yet to pass the exam to use flight instruments. The journey was around 200 miles, but despite the conditions and his relative lack of flight experience, Kennedy Jr. had declined to be accompanied by a flight instructor.

Conditions were dark and hazy, and as the aircraft approached Martha's Vinyard, the sky and the sea became interchangeable. It is believed that Kennedy, who issued no distress call, lost control of the plane which plummeted thousands of feet in the space of a few seconds, suggesting that Kennedy Jr. had become severely spatially disorientated. All three died on impact.

Shortly after the crash, a recovery team undertook the grim and grueling task of recovering the bodies from the bottom of the ocean, while the National Transportation Safety Board set about its investigation into why the deadly crash happened.

Carolyn Bessette had long been a target of tabloid scrutiny thanks to her relationship with John F. Kennedy Jr., and struggled with the attention she received as part of one of America's most famous couples. At the height of her fame, she was routinely criticized for her lifestyle and by those who believed that she had entered into the Kennedy family for personal profit rather than love. She was reportedly frustrated by the fact that some believed her achievements in life were down to her connections, rather than her talents.

Sadly, Bessette's reputation took even more of a hammering in the aftermath of the tragic crash. As noted by The Independent, one story that emerged in news outlets claimed that Bessette had delayed take off on account of a pedicure so that Bessette could have just the right shade of toenail polish. In doing so, it was said that her husband was forced to pilot at night, rather than in the daytime as originally intended, and Bessette was therefore responsible for the deaths of those onboard. 

Several figures close to the couple published "tell-all" books in the aftermath of the fatal crash, some of which painted unflattering portraits of Bessette. She was characterized as a demanding and unpredictable figure who cared more about using cocaine with her friends than she did about her husband, with many commentators also critical of her hesitancy when it came to having children. By the start of the 21st century, Bessette was held by many as the reason for Kennedy Jr.'s downfall, an impression that the Kennedy family did little to dispel.

Tangling with a dynasty as powerful as the Kennedys is no small venture, as the family of the late Carolyn Bessette was undoubtedly aware. Nevertheless, as the years passed and Carolyn Bessette's name continued to be dragged through the mud by various journalists, memoirists, and historians, the Bessette family decided that enough was enough. In 2001, it was widely reported that they had taken legal action against the estate of John F. Kennedy Jr. for the wrongful deaths of the Bessette sisters and that a judge had granted permission for the family to settle to the amount of $15 million, however, an attorney involved in the case told the Cape Cod Times, "I don't know where they got that number." The judgment was consistent with the findings of the investigation into the crash that found that the crash was the result of "pilot error," per The New York Times.

In 2019, Kennedy Jr.'s college friend, the historian Steven M. Gillon, published a new book, "America's Reluctant Prince," in which he was compelled to conclude that his old pal was wholly responsible for the crash that meant the deaths of three young people. Speaking to People, Gillon admitted: "He should not have gone up that night ... At the first sign of danger, he should have done what a lot of pilots did that night and flew inland, away from the ocean, spend the night somewhere and then pick up the next morning ... John bears the responsibility of his recklessness that night and John alone."