Politics JFK Jr.'s Inner Circle Shares Rarely Seen Photos & Touching Memories John F. Kennedy Jr. died on July 16, 1999, in a plane crash that also killed his wife and her sister. Here, friends remember the man behind the famous last name By Liz McNeil Updated on November 25, 2022 11:05AM EST Share Tweet Pin Email Trending Videos 01 of 13 A Forever Bond Sasha Chermayeff/AUGUST John first met his dear friend Sasha Chermayeff at Andover, the elite boarding school he attended as a teenager. Pictured: John and Sasha in 1992. "John always carried a lot of responsibility and weight," Chermayeff says. "I think he had his share of burdens. But in a manner that seemed fearless, he sought out a real life." 02 of 13 Great Expectations Sasha Chermayeff/AUGUST "No one will ever live a life like John F. Kennedy Jr," says Gillon, a historian, author of America's Reluctant Prince and a friend of John's since John's time at Brown University. "There's probably no one who's ever walked the earth that was the focus of media attention their entire life," says Gillon of John, seen here in 1978 at Andover. 03 of 13 A Life of Promise Sasha Chermayeff/AUGUST "There's many layers to the tragedy of his death," Gillon says. John, pictured on Martha's Vineyard in 1992, "had spent his life trying to figure out who he was and what he wanted to do," Gillon says. "And he finally figured it out in those last couple of years. He discovered that his calling was to go into politics." 04 of 13 A Loving Heart Sasha Chermayeff/AUGUST John was the godson to Chermayeff's son Phineas. (They are pictured here in 1993.) "Although there is pain and endless sorrow, I am always so glad to think of him, so glad I got to really know him and I feel blessed by that remarkable twist of fate," Chermayeff says. 05 of 13 No Shirt, No Problem Sasha Chermayeff/AUGUST John (in 1992 on Martha's Vineyard) was often teased by pals about his love of showing off his body. "He had all the physical attributes of a body builder," says Gillon, "but he was a really sensitive caring person inside." 06 of 13 'Alive to the Fullest' Sasha Chermayeff/AUGUST John (here in 1998 in Hyannis Port, Massachusetts, with Phillip Howie, Chermayeff's husband) "was openhearted, compassionate, warm," Chermayeff says. He was "alive to the fullest." 07 of 13 Soaking Up the Sun Sasha Chermayeff/AUGUST John in the summer of 1993 on Martha's Vineyard with actress Daryl Hannah, whom he dated off and on for several years. 08 of 13 Just John Sasha Chermayeff/AUGUST Raised in the spotlight, John carried his fame with natural ease, friends say. Here he is seen goofing off at a dinner party with Chermayeff (right) and her sister, Maro, in 1991. But, says Gillon, "John did not just lead a charmed life. He led a complicated life." 09 of 13 Carefree Memories Sasha Chermayeff/AUGUST John, with Sasha (right) and a few friends in New York City in 1988. 10 of 13 True Confidantes Sasha Chermayeff/AUGUST "John did things with his male friends — ski trips, kayaking, and many travels — but he confided in his female friends, especially Sasha," says Gillon, who befriended John after he became John's teaching assistant in a history class John attended at Brown. John (seen here with Chermayeff in 1988) "was also the best person to get advice from," Gillon says. "He had spent a lot of time analyzing himself and, in doing so, he had a better sense of other people." 11 of 13 A Fond Regard Sasha Chermayeff/AUGUST Chermayeff (here with John in 1991 at her birthday party) was close to both him and his wife, Carolyn Bessette Kennedy. "John and Carolyn were wonderful people," she says. "They fell in love and had a stunning, dream-like wedding. I don't know what would have come to pass ... no one does." 12 of 13 A Friend Remembers Sasha Chermayeff Chermayeff tells PEOPLE she hopes that "by sharing my images, people can see a genuine, loving and kind nature that was both John and Carolyn." (The couple is pictured here on Martha's Vineyard in 1996.) "I sincerely hope people can enjoy the photos and see a taste of something unique in all the perfection and imperfection that was their life," Chermayeff says. 13 of 13 The Way They Were Sasha Chermayeff From left: Carolyn and John on the beach at Martha's Vineyard with Chermayeff's son, Phineas, in 1996.