In a candid conversation with Larry King back in 1995, John F. Kennedy Jr. opened up about his thoughts on mortality. Despite acknowledging that he occasionally pondered his own death, John emphasized that it wasn’t something that occupied his mind too frequently. "It’s just not something that you keep in the forefront of your mind much,” John remarked. Now, twenty-five years after the tragic plane crash that claimed his life at the age of 38, along with his wife, Carolyn Bessette-Kennedy, and her sister Lauren, it’s impossible not to wonder what the future might have held for him. According to Steve Gillon, a close friend and author of America’s Reluctant Prince: The Life of John F. Kennedy Jr., John had every intention of diving into politics. "If things had 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,” Gillon exclusively shared with Closer.
Born just weeks after his father, President John F. Kennedy, secured his historic victory in the White House, John Jr. never experienced anonymity. Yet, despite the constant spotlight, he managed to lead a remarkably level-headed and down-to-earth life. “I have a pretty normal life, surprisingly,” John once said. During his time at Brown University, he dabbled in acting but ultimately graduated with a degree in American studies. It was during this period that he met Steve Gillon, who would become a lifelong friend and confidant. Gillon remembers their routine: "Once or twice a week, we’d jump into his little blue Honda to play racquetball and grab dinner afterward. He always called me Stevie.”
Gillon recalls John as a charismatic undergrad who always seemed to have a group of young women around him. But John was selective about his friendships, choosing those who saw beyond his handsome exterior and famous surname. “He had a role to play — John Fitzgerald Kennedy Jr., son of a slain president — but to truly become his friend, you had to set that aside and accept him on his own terms,” Gillon explained.
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Charting His Own Path: John F. Kennedy Jr.'s Journey
Throughout his life, John was driven by a desire to carve out his own identity, separate from the towering legacy of his family. Unlike many Kennedys before him, John chose not to attend Harvard, though he did follow in his father's footsteps by becoming a lawyer — some say to please his mother, Jacqueline Kennedy Onassis. After serving four years in the Manhattan district attorney’s office, John left in 1993. Just two years later, he co-founded George, a lifestyle magazine that sought to make American politics more engaging and accessible. “I think everyone needs to feel they’ve created something that was their own, on their own terms,” John once remarked.
