The son of an American President, his wife Carolyn Bessette and her sister Lauren perished in 1999 when the plane they were traveling in crashed off the coast of Martha’s Vineyard.

A scion to a family many Americans considered the closest thing to homegrown royalty, John F. Kennedy Jr. lived his final days fraught with concerns: his political/pop culture magazine George was floundering, a recent ankle injury required him to move about with the aid of crutches, one of his closest friends and relative was fatally ill, and his marriage to Carolyn Bessette was strained to the point they were reportedly living in separate residences.

Kennedy, 38, died when the plane he was piloting crashed into the Atlantic Ocean off the coast of Martha’s Vineyard on July 16, 1999. Also onboard were Bessette, 33, and her sister Lauren, 34. There were no survivors.

The deaths were quickly labeled as another example of a tragedy the extended Kennedy family seemingly must endure, including the assassination of Kennedy’s father in 1963, his uncle Ted Kennedy surviving a serious plane crash in 1964, the 1968 assassination of his uncle Robert Kennedy, and numerous other incidents linked to their name.

“There are more of us than there is trouble,” Robert is quoted as saying on the day of his brother’s escape from the plane crash in ’64. “The Kennedys intend to stay in public life. Good luck is something you make, and bad luck is something you endure.”

John F. Kennedy, Jr. and his wife Carolyn Bessette Kennedy arrive at the annual John F. Kennedy Library Foundation dinner and Profiles in Courage awards in honor of the former president's 82nd birthday, May 23, 1999, at the Kennedy Library in Boston, MA.

John F. Kennedy Jr. and Carolyn Bessette Kennedy arriving at the annual John F. Kennedy Library Foundation dinner and Profiles in Courage awards in honor of the former president's 82nd birthday on May 23, 1999, at the Kennedy Library in Boston, MA. The couple died less than two months later.

Kennedy's magazine and marriage were going through rough patches

By mid-1999, Kennedy was facing major decisions about the future of George, the magazine he launched with much fanfare in 1995, a year prior to his marriage to Bessette.

George was expected to lose nearly $10 million in 1999, according to The Kennedy Curse: Why Tragedy Has Haunted America’s First Family for 150 Years by Edward Klein. Michael Berman, a founding partner in the publication, had recently exited the business, publisher Hachette was reportedly losing interest in the title and Kennedy was looking for alternate sources of financing for the venture.

The magazine was also a source of contention between Kennedy and Bessette, who believed George was receiving most of her husband’s attention. Kennedy’s focus on the magazine required him to spend long days at the office, leaving his wife alone in the paparazzi-besieged Tribeca apartment they shared. Bessette hated the media intrusion in their life, something Kennedy Jr. had experienced since birth.

“She couldn’t take it,” recalls Kathy McKeon in her book Jackie’s Girl: My Life With the Kennedy Family. “She wasn’t brought up with it. John was, Carolyn wasn’t… She said, ‘I’m terrified of them,’” McKeon, former personal assistant to Kennedy’s mother Jackie, writes.

Almost three years into their marriage, Kennedy was keen to have children but Bessette was unwilling, according to author Klein, who writes that Kennedy dreamed of having a son. “I hate living in a fishbowl,” the publicity-averse Bessette is quoted as having said to friend. “John may be comfortable living like this, but I’m not. How could I bring a child into this kind of world?”

While coping with marriage issues and a troubled business, Kennedy was also deeply saddened by the news his cousin and best man at his wedding to Bessette, Anthony Radziwill, was gravely ill with cancer.

Bessette's sister organized a lunch to help reconcile the couple

According to Klein's book, on Wednesday, July 14, Kennedy, Bessette and her sister, Lauren, had lunch together at the Stanhope Hotel orchestrated by Lauren, who was concerned the couple was living apart. The book also claims it was over lunch Lauren had suggested she fly with them Friday evening.

The day prior to the fatal plane crash, Kennedy visited his orthopedic surgeon at Lenox Hill Hospital. He was there to have a cast removed from his ankle which had been broken weeks prior in a paragliding accident. Though free of the cast, his ankle was still tender, requiring continued use of crutches.

The cover of the 'New York Daily News' featuring John F. Kennedy Jr. and Carolyn Bessette after their plane crashed on July 16, 1999

The cover of the 'New York Daily News' featuring John F. Kennedy Jr. and Carolyn Bessette after their plane crashed on July 16, 1999.

JFK Jr. got his pilot's license only a year prior to the crash

On the morning of July 16, Kennedy reconciled with Bessette over the phone, writes C. David Heymann in American Legacy: The Story of John & Caroline Kennedy. The plan for the evening was to fly to Hyannis Port, Massachusetts, via a stop at Martha’s Vineyard to drop off Lauren. Kennedy and Bessette were scheduled to attend the wedding of Kennedy’s cousin, Rory Kennedy.

Kennedy and Lauren left Manhattan for the Essex County Airport in New Jersey – where Kennedy’s high-performance Piper Saratoga light plane was waiting – a little after 6:30 p.m. Carolyn arrived separately, sometime after 8 p.m. Coinciding with sunset, the Federal Aviation Administration cleared the plane for takeoff at 8:38 p.m.

Kennedy, who attained his pilot’s license a year previous, was in the pilot’s seat of the plane he purchased less than three months prior. The Bessette sisters sat side by side behind him. Following takeoff, Kennedy checked in with the control tower at Martha’s Vineyard, but the plane was reported missing after it failed to arrive on time.

State Police hand GPS coordinates to Environmental Police for a dive site concerning the JFK, Jr. recovery effort approximately two miles southwest of Gay Head.

State and Environmental Police during the JFK Jr. plane crash recovery efforts off the coast of Martha's Vineyard on July 19, 1999.

The weather and Kennedy's 'failure to maintain control of the airplane' were factors in the accident

Following an exhaustive search, fragments of the plane were discovered July 19. A day later divers found the remains of the shattered plane strewn over a broad area of seabed. The search ended July 21, when the three bodies were recovered from the ocean floor.

The National Transportation Safety Board determined pilot’s error was the probable cause of the crash, due to Kennedy’s “failure to maintain control of the airplane during a descent over water at night, which was a result of spatial disorientation. Factors in the accident were haze and the dark night.” Autopsies conducted on the evening of July 21 revealed the victims had died upon impact.