My Friend John

updated 07/20/2009 AT 01:00 AM EDT

originally published 07/20/2009 AT 01:00 AM EDT

On a July night 10 years ago, Sasha Chermayeff joined her close friend John F. Kennedy Jr. for dinner in Manhattan. Afterward, as the two walked home through the city streets, Kennedy turned to her and said: "I really want to have a child."

Eight days later he was dead at 38. Kennedy, disoriented due to poor visibility, lost control of the plane he was piloting, a single-engine Piper Saratoga also carrying his wife, Carolyn Bessette Kennedy, 33, and her sister Lauren Bessette, 34, and crashed into the Atlantic on a flight from New Jersey to Martha's Vineyard. The sudden death of yet another handsome, youthful Kennedy shocked the world—and left many unanswered questions as to what might have been. "I always thought," says Sasha, who met John when he was 15, "that he would have achieved something great, something that would have had meaning to him and to other people."

Grief-stricken after John's accident, Sasha gathered up the letters, funny postcards and photos documenting their friendship and placed them in a cardboard box under her bed. But as the 10th anniversary of his death approached, Chermayeff, 49, now an artist living in upstate New York with her husband, Philip Howie, son Phineas, 16 (who was John's godchild), and daughter Olivia, 13, decided she was ready to share her private memories of John. "Why not remember him happy?" she says. "People really loved him. I certainly did, in the deepest part of my heart."

This personal collection reveals a man who was playful yet reflective, and one who was wrestling with his future and pondering his next steps—possibly into politics. "He had both the pros and cons of an incredible life," she says. "But also, all of the confusion. He wanted to ... develop and at the same time, step up to the plate to a very large legacy." The carefree teen she had first met in 1976 had become a thoughtful man. "Things were getting pretty clear. I don't think he was going to be wasting too much time," she says. "He had an awareness of life, and I think he was going to seize the moment. He was really poised for the next part of his life—and then he was gone."

A Wandering Man

John's letters, sent from all over the world, reveal a privileged young man searching for a mission. He traveled throughout Asia and Africa and lived in India for eight months after graduating from Brown. "At first he was in culture shock," says Sasha. "This was not the tourist circuit. He wanted to see the world first before he could figure out how to give back. There's one letter where he was sick for a week and had to take the bus to another town for lab tests. He'd make a joke about it, but he also knew it was par for the course for many people. [When] he was on third-class trains in the middle of nowhere ... he was able to come to terms with what he wanted to do." His travels also led to adventures of another sort. In one note from India, "he mentioned hooking up with a German woman whose English wasn't very good—he said the language barrier made things more interesting."

The Inner Circle

Sasha and John always celebrated their birthdays together. "If he got to know you, he loved you, and then you were part of his world," notes Sasha. "He got so famous that he kind of liked this intimate group of friends that he had known a long time. I think he was relaxed when he wasn't the central figure." John was also a frequent sleep-over guest: "He'd call me in the middle of the night saying he lost his keys and throw rocks at my window and then sleep on the floor."

Sexiest Man Alive?

Even though John—who sometimes signed his letters (above) "Juan"—and Sasha were never romantically involved, he was "stunningly gorgeous," she says. "Though he had every right to be, he was not vain. He was just at ease. He was really over it. Maybe everyone else wasn't, but he was like, 'Look, this is me.'" Still, he exercised for at least an hour a day, 365 days a year. It wasn't unusual for houseguests to wake up and find he had already completed an eight-mile run. "The guys felt a little bit of a need to keep up," she says, "and it was kind of fun to see them staggering along."

'They Were In Love'

"Being photographed, that bothered her," says Sasha of Carolyn Bessette, whom John began dating in 1994. "It was hard for her to adjust." And even though she was "very strong," the nonstop attention after the wedding shocked Carolyn. "It became clear that her life had completely altered," Sasha says. "He tried to help her with it, but he had 38 years of practice and she had 10 minutes. She would have come around if she had time." As for rumors of a troubled marriage, she says, "They were in love. It was not a show for our benefit."

'He Would Have Been A Great Father'

"Olivia had fallen asleep in his arms," recalls Sasha of this shot at left—her favorite—taken on a Hyannis Port boat ride in 1998. "The water got rough, and she just reached out to John. He was so proud. I think that seeing us with our children made him think, 'Yes, I can do this.' I used to say to him, 'Why do little kids follow you? Is it because you're handsome and a Kennedy?' The beauty is that kids are blind to all that. That's the expression you see there. He appreciated that."

Sasha sometimes also saw John's somber side. "He went through a lot of things that were painful for him," she says. "He'd been through so much, but he wasn't a big complainer." Once, walking with John and her son, who was 3 at the time, "I said, 'Oh my God. Phinney is the same age that you were when your father was killed.'" John replied, "You never get over it."

Flight School

Carolyn sent a postcard (above, right) from Vero Beach, Fla., where John took his flight training in 1998. He loved the freedom of flying, says Sasha: "He liked avoiding the whole airport scene, where he felt confined and trapped." In the card, she notes, "Carolyn said they were having a lot of fun in Florida. She said we'd all be flying up together to Martha's Vineyard by next summer."

Sasha and her family spent two long weekends with John just before his death. "The circumstances of his life forced him to hold onto those things that were important," she says. "He was looking for what he wanted to do in his life. He was going forward with clarity and not in a fog."

The Final Pictures

After John broke his ankle in a paragliding accident in late May 1999, he told friends he thought it was meant to be. His cousin Anthony Radziwill was dying of cancer and was about to move into John's house on the Vineyard for the summer. "John said the reason the accident happened was because he was just going to slow down and spend the rest of the summer sitting in a chair, next to Anthony," Sasha recalls. "There would be nowhere for him to go because he was in a cast. And this was going to help him face what was coming—the death of his close friend and cousin. He was very brave." Before the summer was over, however, John was gone.

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