On the evening of July 16, 1999, John F. Kennedy Jr. took off from Fairfield, New Jersey in a single-engine Piper Saratoga plane that he piloted himself. His plan was to drop off his sister-in-law in Martha’s Vineyard, then continue on with his wife to Hyannis Port, Massachusetts to attend his cousin Rory Kennedy’s wedding the next day. But he never made it to the wedding because the plane crashed, killing John, his wife Carolyn Bessette-Kennedy and her older sister Lauren Bessette.

The death of JFK Jr. was a major news story, not only because the 38-year-old was the son of former president John F. Kennedy, but because of the uniquely public history of unexpected deaths in the Kennedy family. JFK Jr.’s father was assassinated in 1963, as was his uncle Robert F. Kennedy, in 1968. Just two years before JFK Jr.’s death, his cousin Michael Kennedy died in a skiing accident.

“It seemed incomprehensibly cruel that John would actually live eight years less than his father…who was cut down at the age of 46,” Christopher Andersen, author of The Day John Died and The Good Son: JFK Jr. and the Mother He Loved, writes in an email to HISTORY. “[P]eople were also blown away by the Bessettes’ loss of not one but two children—and trying to comprehend how a family comes to terms with such a devastating loss.”

John Fitzgerald Kennedy Jr. was born on November 25, 1960, two weeks after his father won the presidential election. The public knew him as “John-John,” and saw pictures of him as a toddler playing under his father’s desk in the Oval Office. After his father’s assassination on November 22, 1963, John-John attended his father’s funeral on his third birthday. His mother, Jackie Kennedy, told him to salute his father’s casket, and a picture of him doing so appeared in newspapers and magazines around the country.

Although Kennedy continued to be a known figure whose name occasionally appeared in the news—in 1972, the Greek government charged eight people with plotting to kidnap him—he maintained a relatively low profile. That shifted in 1988, when he introduced his uncle Ted Kennedy at the National Democratic Convention.

After that, the media started covering him a lot more often. In September 1988, People magazine named the 27-year-old law school student “Sexiest Man Alive.” The next year, he graduated from law school and got a job as an assistant district attorney in New York City. His failure to pass the bar exam on his first and second attempts made headlines, with reporters noting that if he failed his third attempt, he’d lose his job. He passed in 1990 and remained in his position until 1993. Two years later, he launched George, a politics and celebrity magazine based in New York City (it folded in 2001, after his death).

During the early 1990s, tabloids covered Kennedy’s romantic relationships with celebrities like Sarah Jessica Parker and Daryl Hannah. In 1996, he married Carolyn Bessette, a publicist for Calvin Klein, in a private ceremony that the couple managed to hide from prying paparazzi. The media often focused on Carolyn as a style icon, but according to Elizabeth Beller, author of Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy, what people close to her remembered most after the 33-year-old’s death was her compassion for her friends and family.

Kennedy began to pursue his interest in flying in December 1997, and received his private pilot’s license in April 1998. By the time he, Carolyn and her sister Lauren took off for Martha’s Vineyard on July 16, 1999, he was certified to fly under “visual flight rules,” meaning he was able to use visual cues to guide him when weather conditions were favorable. However, he did not hold an instrument rating, meaning he was not proficient in using a plane’s instruments to navigate through low-visibility weather.

Around 6:30 p.m. on the evening of his flight, Kennedy viewed a weather forecast that indicated visibility would be good during his flight. Yet by the time he took off from Fairfield at 8:38 p.m., the skies were hazier and visibility was reduced. Kennedy likely became disoriented in the haze, as the National Transportation Safety Board concluded in a report it issued a year later, causing the plane to crash about an hour into its flight.

When Kennedy didn’t arrive at Hyannis Port that evening, a relative reported him missing. The next morning, the U.S. Air Force and the Coast Guard launched a search for the plane. Searchers identified a suitcase belonging to Carolyn’s sister Lauren Bessette on a beach in Martha’s Vineyard, where the the 34-year-old investment banker and twin sister of Lisa Ann Bessette had hoped to meet up with friends the evening before.

“As it became increasingly clear there would be no happy ending, there was shock, awe and a palpable sense of grief,” Andersen writes to HISTORY.

On July 21, U.S. Navy divers recovered the bodies of John, Carolyn and Lauren from the plane’s underwater wreckage. The next day, the Kennedy and Bessette families scattered their ashes in a private ceremony at sea.

“John’s death really amplified the mythology around the Kennedys,” Andersen adds. “They are the closest thing America has to a royal family, and John was their Crown Prince.”

Of course, the Kennedy family was not the only family that lost someone in the crash. Carolyn and Lauren’s mother, Ann Freeman, later reached a wrongful death settlement with JFK Jr.’s estate.