In 1995, John F. Kennedy Jr. admitted to Larry King that he did sometimes think about his own death, but that didn’t stop him from living his life. “It’s just not something that you keep in the forefront of your mind much,” John said.

Twenty-five years after the plane crash that ended John’s story at age 38 — and claimed the lives of his wife, Carolyn Bessette-Kennedy and her sister, Lauren — it’s hard not to wonder what might have been. “John had every intention of getting into politics,” Steve Gillon, a friend and the author of America’s Reluctant Prince: The Life of John F. Kennedy Jr., exclusively tells Closer. “If things turned out differently, he might have run for governor of New York in 2001. I think he probably would have run for president in 2008.”

Born just weeks after his father, John F. Kennedy, won the White House, John never knew anonymity, but grew up levelheaded and down-to-earth despite all the eyes upon him. “I have a pretty normal life, surprisingly,” said John, who dabbled in acting as an undergrad at Brown University but graduated with an American studies major. Gillon, who would remain a lifelong friend, started out as a workout buddy. “He always called me Stevie,” says the historian, college professor and author. “Once or twice a week, we’d get in his little blue Honda to go play racquetball and have dinner.”

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The handsome undergrad “always had a gaggle of young women around him,” remembers Gillon, but John chose his friends from the people willing to look beyond his handsome appearance and famous family name. “He had a role to play — John Fitzgerald Kennedy Jr., son of a slain president — but to become his friend, you had to cast that aside and accept him on his own terms.”

John F. Kennedy Jr. Becomes His Own Person

Finding his life’s purpose beyond his family legacy would be a theme throughout John’s life. As a young man, he broke with Kennedy tradition by not attending Harvard, but he did become a lawyer — some say to please his mother, Jacqueline Kennedy Onassis. After four years in the Manhattan district attorney ’s office, he left in 1993. Two years later, John cofounded George, a glossy lifestyle magazine that attempted to make American politics sexy. “I think everyone needs to feel they’ve created something that was their own, on their own terms,” John said.

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Gillon became a contributing editor at George and helped by writing editorials. “John spent his entire life trying to develop his own identity,” he explains. “That’s why he avoided politics for as long as he did, because he didn’t want to just live the life other people wanted him to live. He wanted to live his own life.”

Yet John’s charisma, ease with public speaking and generous heart made him a natural leader. He was just beginning to realize that perhaps he was born to be a political contender. “He had spent the day in Harlem skating with a bunch of underprivileged, minority students,” recalls Gillon, to whom John confided his aspirations over dinner. “He said, ‘What people need is hope. They need to know that the future can be better than the past. I could do that, I could give them hope.’”

John F. Kennedy Jr. Was a Special Friend

Gillon misses John’s optimism, enthusiasm and sense of humor the most. “He made you feel good,” he says. “He was so upbeat and had such a positive view of life that it was contagious.”

And although he liked to tease his buddy, John would do anything for him. When Gillon complained to John that the History Channel, where he worked as a commentator, wouldn’t consider him as a program host, John stepped in. “They said John F. Kennedy Jr. called and said he would do a 30-minute interview on what would have been his father’s 80th birthday under one condition, that I be the one that hosts it,” recalls Gillon. “That’s the kind of guy John was. He is responsible for my entire career at the History Channel.”

Because he died so young, John’s story will always be one of lost promise. “By the time he turned 38, he knew he wanted to go into politics — not because his family expected him to and the public wanted him to, but because he discovered it himself,” says Gillon. “He also showed that someone who is born into this family where all these expectations are imposed on you could still turn out to be a normal person.”

Gillon feels certain that John would rather be remembered for the way he lived his life instead of how he died on that foggy night in July. “I think he would want people to remember him as a caring, kind and thoughtful person,” says Gillon. “As someone who loved life and who enriched the lives of a lot of people: I think that is his legacy.”