His death marked the end of a dynasty. Just before 10 p.m. on July 16, 1999, the Piper Saratoga plane John F. Kennedy Jr. was piloting plummeted into the Atlantic Ocean off the coast of Martha’s Vineyard, Massachusetts, instantly killing the political scion, wife Carolyn Bessette, 33, and her sister Lauren Bessette, 34. Investigators determined that the amateur pilot — who’d broken his ankle in a paragliding accident six weeks earlier — suffered from spatial disorientation while descending in the foggy night. Takeoff had been delayed almost three hours after John and his sister-in-law got stuck in traffic en route to a New Jersey airport and Carolyn insisted on getting a pedicure. Divers discovered their bodies, still strapped into the wreckage, five days later.

Now, nearly 25 years later, the world remains fascinated by the doomed fairy tale of the political prince. In the decades since the tragedy, heartbreaking details of the love and loss have emerged about the dashing son of the late President John F. Kennedy and his style icon wife, Jacqueline Kennedy Onassis, with people close to the heir of the political dynasty and founder of the buzzy magazine George continuing to reveal secrets of his too-short life. “I don’t believe John ever fathomed that he would die at 38,” friend Lisa DePaulo told one outlet. “He didn’t buy into things like the Kennedy Curse.”

Despite the trauma that plagued his family, John enjoyed a charmed if complicated life. “Jackie was fiercely protective of her children and was determined to give John and his sister [Caroline Kennedy Schlossberg, 66, now the U.S. ambassador to Australia] as normal a life as possible,” a source exclusively tells In Touch. “After JFK’s assassination, she did everything she could to shield them from the spotlight,” including moving them from the fishbowl of Washington to NYC, “where she felt they could have a more anonymous life. She did not pamper them — John even rode the public bus, with Secret Service men following behind.”

No longer the little boy saluting his father’s coffin, John moved to Rhode Island for college. “Jackie pushed hard for John to go to Brown and even filled out his application for him because he was away in Africa,” recalls the source, noting, “John had a passion for world issues and civil rights, his father.” He was an outgoing student with a curious mind, “but when it came to his studies, he lacked discipline — at one point he ended up on academic probation,” adds the source, who says though John went on to law school at NYU, “for him, college was more about having fun and exploring than it was about getting perfect marks.”

After moving back to NYC, he became a tabloid fixture, making headlines when he finally passed the bar exam on his third try. “It made a rough situation that much worse,” says the source. “The frenzy around his love life was unbearable at times.”

Yet John relished his role as America’s most eligible bachelor. He was linked to a slew of famous women — including Sarah Jessica Parker, 59, Daryl Hannah, 63, Brooke Shields, 59, Cindy Crawford, 58, and Madonna, 65, who a pal says left him racy voice messages. There’s even speculation that JFK Jr. enjoyed a spark with Princess Diana two years before her death. The duo enjoyed a secret meeting in her suite at NYC’s Carlyle Hotel in 1995 when John tried, unsuccessfully, to convince her to pose for George. The magazine’s creative director, Matt Berman, who wrote the 2014 memoir, JFK Jr., George, & Me, said that John had remarked how tall, shy and demure she was and had confessed, “She’s got a great pair of legs.”

But the love of his life was Carolyn. Though the public had an image of the former Calvin Klein publicist — whose fashion prowess rivaled Jackie’s — as “icy,” “cold” and a “shrew,” in real life she was “warm and effervescent,” Elizabeth Beller, author of the new book Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy, told ABC News. John never forgave himself for failing to introduce Carolyn, whom he dated on and off for two years before they wed in 1996, to his mother before Jackie’s death at 64 in 1994. “Jackie was quite sick [with non-Hodgkin’s lymphoma] and it wasn’t a moment to [meet] a new girlfriend,” Beller explained, “but he told many friends … one of his biggest regrets in his life was not introducing them, because that… hurt Carolyn.”

Though she was his great love, their marriage was struggling before that fateful plane ride. “They were going through a rough patch,” says the source, pointing to reports they’d tried marriage counseling, argued over Carolyn’s cocaine use and were even living apart in those final days. “They were at odds over having children — he was ready to start a family and she wasn’t sure she wanted to bring kids into their world,” explains the source.

Inside the Private Life of John F. Kennedy Jr. and Carolyn Bessette 25 Years After Their Deaths
Arnaldo Magnani/Getty Images

According to John’s friend Steven M. Gillon, he “struggled his entire life to have an identity that was separate from his family. He always said, ‘I don’t want to do what people expect me to do. I want to do something different.’”

But the historian and friend of the charismatic attorney for two decades believes JFK Jr. — who he’s said explored running for a N.Y. Senate eat and had ambitions to run for governor — had dreams of eventually making it to the White House like his father. “I think about it often, how much better off our country would have been had John not made the foolish decision to take his plane up on the hot humid July evening,” Gillon has said. “The one thing John will always share with his father is this sense of what might have been.”

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