Littell describes his friend as a man motivated by a strong sense of decency and a determination to do good for his friends, as well as those he didn't know.
"To a certain extent, there's a guy who wanted to do the right thing, had the tools to do the right thing and went out and did the right thing," Littell said.
John F. Kennedy Jr. and Rob Littell pose in this undated photo. Courtesy of Rob Littell.
But what may be most compelling about Kennedy is that he had very clear political ambitions, according to his friends.
"There is no question in my mind whatsoever he wanted to be president of the United States. He wanted to lead the American people and he wanted to do it from a position of strength that he didn't owe anybody," Littell said.
His creation of George magazine was part of his political plan and Littell said he remembered Kennedy's frustration when he heard Hillary Clinton was going to run for senate from New York.
"I remember him up at the vineyard showing me the announcement in The Post and he threw it down, the paper, in good humor," Littell said. "He said, 'She is taking my seat.'"
Kennedy never admitted any political aspirations publicly.
Politics is a path many speculated Kennedy would take, perhaps even toward the nation's highest office. But aside from politics, Littell said Kennedy had plans to become a father.
"His immediate excitement was about having a family in 1999," Littell said. "I talked about it with him. I talked about it with his wife.
"He was just a super sweet guy. He probably could have fit 15 kids on his lap and he would have been a hell of a dad," Littell said. "We are missing a great dad out there, I know that."
Had Kennedy lived, he would be 48 years old today and Littell believes he may have had a career path similar to that of President Barack Obama.
"I'm not sure I predicted that John would go for 2012, but things move quickly. Obama showed up, he had three years as senator, so they probably would have had a similar set of experiences. Obama is a smarter guy, but John has the world experiences and the same level of charm," Littell said. "It's fun to think about Obama versus Kennedy."
Littell thinks of many possibilities Kennedy could have had, but harbors some resentment toward his friend.
"I'm still angry at him. Frankly, he shouldn't have been up there and obviously he shouldn't have crashed," Littell said. "He hurt himself; he hurt other people and the victims were the ones who had to mourn. So, yeah, I'm angry at him."
"We loved the guy. I loved him. America loved him. He knew that and he wanted to give it back, which is a pretty neat thing about him," Littell said.
Kennedy had a vast impact on Littell's life.
"I remember John every day. I remember him as a great person and I remember him as someone that helped me get me through every day," Littell said. "I feel very lucky to have known him."