A friend and classmate at St. Paul's School and roommate at Yale.

…Both of us had been there [St. Paul's] a couple of years already, but I didn't really know John well until that meeting. John was in Father John Walker's apartment, and I walked into the apartment … and Father John said, "Oh, this is Danny. This is John Kerry. He's feeling bad about himself, because he thinks people don't like him." Or something to that effect. And we laughed. We made him feel so silly about feeling that way that it immediately cheered him up and we became friends.

Why was he feeling badly?

Well, I think like all of us, in prep school, you get sort of low at times. I think he went to Father John and was talking about his life at the school and his relationship to classmates and so on. I guess he wasn't the most popular guy, I imagine. It's apparent that he wasn't the most popular guy. I think it bothered him. He didn't know why, didn't know what about him would engender that.

After meeting him and talking with him that evening, I said, "I think you're a great guy, you know? You shouldn't feel -- Who cares what they think? You know, you're fine."

Did he not fit in?

There was a society there that was the really core society of the school, which would be the boys who had families that had been there and who wore the right clothes and knew the right things and had a lot of money. And John, I don't think, is part of that society at all -- nor was I. I think he was more interested in just being able to talk seriously to somebody without any of that baggage. John just completely ignored the sarcasm and the sort of cliquishness that went on at prep schools in those days. It just wasn't his nature at all. …

Author of Tour of Duty - John Kerry and the Vietnam War.

…Well, first off, you have to look at his mother and father like you do when you do a biography of anybody. Richard Kerry not only was a pilot in World War II, but was a civil servant. He did not come from money. Real name was Kohn -- it got changed to Kerry. His father committed suicide. There was, on his father's side, a kind of bankruptcy that had occurred in the family.

He was simply getting paid civil servant paychecks when he was working in Washington or Berlin and Oslo -- not much money. Rosemary, his mother, did come from the Forbes clan of Massachusetts. It's called old money. But that old man had gotten worn down.

John Kerry only went to prep schools because he had an aunt who had the money to pay for his way into those prep schools. So here's somebody who couldn't afford to go to those. So while he was going there, he knew that his mother and father did not have the money to even send him there.

Look, you don't have to feel sorry for this person. He's coming from a pedigree of sorts from his mother's side of the family, and there's access to money. He was never without pocket change. But when you're in your teens and your peers are coming from these very wealthy families, you're going to spend your weekend at their mansions on Long Island or beautiful homes on Cape Cod.

Kerry was sort of a rootless guy, always staying in the extra bedroom of these houses. He was kind of feeding off of that establishment. Because of it, he seemed to be more of a striver. There was a feeling at prep school where Kerry was, that when you come from a lot of money, you come from a lot of wealth, you would carry yourself with a bit of detachment, and a bit of an air of superiority, or you didn't have to learn -- you came from a kind of trained aristocracy.

Kerry was always striving, always trying to be number one. Always trying to overdo it, in that he had an overachiever status. I saw this once when I wrote a book on James Forrestal, who had that same thing -- an Irish Catholic, and you watch his way through prep schools and into Princeton -- always pushing harder than everybody. It grates on some people. He wants to win the debate; he doesn't want to be the head of one club, but head of three clubs. ...

So Kerry is, from earliest age, we can determine, more openly ambitious than other members of this tiny little world he's in?

I think he's more ambitious than just about anybody that you would encounter. But that ambition comes out of a great love of history and politics.

I looked through his archive, and it's stunning to see the correspondence. In college at Yale, he has a letter from Claire Boothe Luce and a letter from Clementine Churchill, and photographs of himself with four or five U.S. senators. He has already had personal photos and encounters with President John Kennedy, and is dating Janet Auchincloss and is rooming with Harvey Bundy. It's extraordinary stuff when you go look through the scrapbooks of John Kerry in this period. He's somebody who is consciously putting himself in that milieu, when Richard Kerry and Rosemary, his parents, weren't really fully part of that.

It's not like the parent is sort of putting a booster rocket on the kid and saying, "You are a child of destiny." It's somehow coming from within him somewhere?

I think it's coming from his love of history and his great readings that he did as a child on biography, of reading a lot of Winston Churchill, who was his first early hero. It's the Churchill of the Boer War and that he could be the swashbuckling hero.

John Kerry has a very vivid imagination as a young person. I mean, he actually did go and take his bicycle from Norway to go camp in Sherwood Forest to be around the ghost of Robin Hood. His father's sense of New England patrician background comes a lot from Emerson and this incredible notion of self-reliance, and also Emerson's essay, which Bobby Kennedy loved, on what is a hero.

John Kerry wants to be the hero in his own drama. He likes King Arthur and the Round Table. He likes the young swashbuckling Churchill, and he loved the early antics of Theodore Roosevelt. He is going to become a great American hero of some sort, I believe, and it's through history and reading, more than [through] his father.

What his father gave him, though, was this notion of self-reliance. His dad used to blindfold him in the fog, put him on a boat in the harbor, and say, "Make your way back to shore without seeing," meaning, "I want to learn how to navigate by feel." Not many parents go to that extreme of teaching a kid the need for self-reliance.

John Kerry told me in an interview once how he used to go by himself and walk from Berlin, in the height of the Cold War, from their house. Walk to a train station, buy comic books and candy bars, and have to go commute back to Switzerland on a train by himself. He'd be looking out the window at Soviet troops with the guns, and he's all alone.

He got yellow fever when he was in Switzerland boarding school. He was dying for his parents to come see him, and his mom and dad never came to visit him. They were living in Berlin. ... It was very lonely. So he turned to history. He turned to figures in history. Books became a great friend to John Kerry as a young man.

When I've read this correspondence, there's one from Switzerland I read. It goes on for pages about every detail of what it was like there. He's somebody very well aware of the world of letters and the world of politics and the world of heroism. …

Fellow student at St. Paul's School and Yale.

…We've talked to people that went to school with him. And there was a feeling of not only being an outsider, but of being unliked, unpopular.

…he was high energy, as he still is. He sort of put his cards on the table, and said, "I want to do this, or I want to do that. I'd like to be a member of the hockey team. Or I want to maybe one day enter politics…." Or whatever he might have said. These were the kinds of things that kids at Saint Paul's generally didn't say. And so, I think his tone, and his energy, and his seriousness, but you know, it wasn't all seriousness, he was also a lot of fun… But still, there was a lot of seriousness, I think.

Some people have said that he was a striver. That's been used to describe him at that time. Others have described him sort of in the classic nerd sense.

I'd say he was probably both. And then a third quality as well, which is he just threw himself into whatever it was going on. And you know, he wasn't perfect at anything. But he was good at a lot of things. And he was a good athlete, a good musician. He was a good student. And he was certainly energetic around his friends.

So yeah, he was a nerd, in that he actually looked into his books, and studied them, and came out well. He was a striver later. I mean, not sure I would have necessarily said that was the case when he first was there. …

[To] understand John, or myself, or many of the other people from our generation who went ultimately into public service … we were captured by Kennedy. And especially at Saint Paul's. And there was something about Kennedy that seemed to make the outside world seem incredibly attractive and demanding.

… So, by the time I'm a senior and John's a junior, and the Kennedy era has really come, it was a pretty dramatic time. … And you know, at that stage, John really had become a striver in a political sense. He founded an organization that is called "The John Winant Society." I think it still exists. It was the school political organization. …

Older sister.

…There's a fearlessness about John that everybody remarks about. Did you see that when he was a child?

Yes. Yes. (laughter) He just kind of pushed all the limits. I do remember once, it was in Millis [Mass.], and he was just dashing through the house, got to the door and he was really anxious to just dash out. And he pushed his hand through the window and cut himself quite badly.

But he was just fearless. He was running out to go on some adventure. And you certainly see that in his athletics. I mean, he's on the edge of everything he tries. And it's something that he always said to all his siblings. It was--you really have to do the best you can. And it was testing himself.

He preached that to you.

He preached that to all of us, yes. Go out there and do the best thing that you can do. He really had a sense we have to go out there and be the best we can.

…

Your father. What kind of man was he, as a father?

My father was a very distant person, because as we learned later on in life, his father had committed suicide when he was three or four years old. And I think that made obviously a big impact on him. He grew up without a father. So I think in many ways he didn't have a model to kind of show him what to do. And I guess by the time Diana and Cam came along, that he kind of was getting it a bit more. But his personality was a very withdrawn personality. Right up until he died when he was 84, he was a difficult person to know.

And what impact did that have on his first son, do you think?

I think that he found he liked to compete with John. In sports. Perhaps that's why John is so good at a lot of the sports that he excels in, because my father kind of took him on, challenged him. They were great competitors. Especially in skiing.

But he had the distance, the lack of effusive sort of expression. Is that something that was difficult for John, do you think? It was difficult for you?

I think it was difficult for both of us.

And your mother?

My mother was a very, very warm and loving person. She was really incredible. She was the role model for all of us in terms of involvement in public service. She was a Girl Scout leader for many, many years. She volunteered in hospitals. She actually had been a nurse in France. And she was a conservationist.. …Public service was her life.

It is written about quite a bit that John is aloof. And we can argue about it. But I can't help but listen to you and think-- well, is this a reflection of your father?

I think both my parents were very, very shy people. And I think that there's a shyness in all of us. I think that Diana and I are perhaps more gregarious than John and Cameron are. Perhaps that's the nature of women, I'm not sure. But John and Cam are both remote, in some ways. I wouldn't use the word "aloof." But John, once you get to know him, is really a warm and open and funny human being. …

Brother.

…What kind of guy was your dad?

Extremely intelligent, powerful intellect, very involved in ideas--and both in his work and later on in his life, writing about American foreign policy. He would certainly challenge us at the dinner table. And my dad was somebody who appreciated a logical argument, and was quick to point out the errors in logic and one that wasn't logical.

So he, in contrast to your mother…?

My mother was less intellectual about her approach to things. And much more intuitive.

They describe two parts of John Kerry in a way.

Oh, absolutely. Very much so. I think the sense of services comes from both of my parents. …

Was your dad hard on John?

No, I wouldn't say that my dad nor either of my parents were hard on us. I mean, it's funny, we were never pushed. We always had the sense that somehow the things that we did or the things that we accomplished were expected of us. But it wasn't the sense that if you didn't achieve them, that there was pressure, a sense of any kind of sense of failure, disappointment from my parents. They were always very supportive in the things that we did.

There is a story that Douglas Brinkley talks about. Your dad putting blindfolds on you.

Actually, not blindfolds on us. He was blindfolding himself. You asked where John sort of got his drive. My dad could be pretty driven about things. And the story of him learning how to navigate -- he was learning how to do instrument navigation, so he put himself under a blanket to navigate strictly by instruments, while John was the lookout to make sure he wasn't crashing into anything.

In the boat and this was sailing?

In the boat, yes. Dad was an avid sailor. He sailed a boat across the Atlantic a couple of times. A small boat. Once, I think, about a 45 foot boat. And another time in a 35 foot boat. … John was on one leg of my dad's first trip. He and a group of school friends sailed from Bermuda to the States.

How do we account for how driven your brother is?

Some of that, I think, is just hard-wired. I think he was probably that way in the crib. I mean I think my mother has described him a little bit that way -- a kid who was active, in a hurry. That's part of just the way that he is. I mean if there was something that we got from our parents that produced that, I think both of my parents had kind of a sense of adventure-- they were adventurous in their lifetimes. And I think that my dad was a pretty competitive person. …

You also were a family with a lot of international living experience. How did that affect John's views of the world?

Well, we were very much exposed to the consequences of the World War and saw Europe in the wake of the war. And I remember going as a small child to the Normandy beaches -- there was still very much the evidence of war. You could see the burned out hulks of Jeeps and landing craft that were there. And the bomb craters. And you saw that across Europe. I remember when we moved to Berlin there was still bombed out and shot up and burned buildings. … And we were there in an era when America was still being greeted as the liberators. …And you'd stay in a hotel and there'd be a plaque there that said "This hotel was rebuilt with assistance from the Marshall Plan."

So we really saw the build-up of what some people call American soft power. The power of American ideals and involvement. …