• Highlights from this interview
• First impressions of a young Obama
• How he found a sense of roots, community in Chicago
• Why he pursued a law degree at Harvard

How did you meet Barack Obama?

We had put an ad in a number of newspapers for a community organizer in South Side of Chicago, and Barack sent me a résumé. We then did a phone interview. And based on that phone interview, I decided I wanted to interview him in person. I was going to New York City anyway; my dad lived on the Upper West Side. I arranged a meeting in a coffee shop on Lexington Avenue, offered him a job, and he said yes.

The way it's been written is, you get off the telephone with this guy; you don't even know quite what his race is. So take us to that telephone call.

At this point, I'm looking for anybody who might be a good organizer. But I particularly need somebody who's African American because I'm doing the organizing in the large African American portion of the area we're organizing, and it's tough to get doors opened. It's tough in terms of the way ethnic politics play out in Chicago. We really need somebody who can be identified as an African American organizer.

And I talked to Barack, and there's really no way to tell if he's African American or not, except somewhere in the conversation he indicated some kind of interest in some African American activities at Columbia. So I thought he was. But when we're through the interview, I'm looking at the name, which is Obama, and I see he's from Hawaii. I'm fairly convinced that he must be Japanese. ... So I really did not know much about him initially, but my job was to learn as much as I could about him in the interviews.

So you sat down with him in a diner. Tell me about that meeting.

... The surface impression was that he was personable. For 24 years old, he seemed relatively stable emotionally, fairly confident.

What was important for me was his motivation. The whole purpose of this interview for me was to ascertain his motivation, because we had not had good experiences with people who were as young as he was in organizing. They would burn out very quickly. ... And the fact that someone had been successful in previous endeavors, including in their academic career, was not necessarily a plus in terms of the organizing, because young people who have been successful would, for the first time in their life, encounter significant failure, and they would often unravel on us.

So I wanted to see whether his motivation made sense to me and that he'd be able to withstand some of that stuff in the early stages learning the work. And the way I needed to do that was to get as much of his story as possible. The organizing itself was always based on a narrative, which gave Barack a good jump start with the work, getting to know people's stories and building a relationship with them around [those stories], and then challenging them to move out of that story, to change their life along with other people in the present.

So it was natural for me to try to pull Barack's story out of him, and I did. And based on that story, I was convinced that he had a good shot at doing the work. What I noticed about his story, that I responded to, were three things. First of all, Barack was, to my mind, an outsider. He had been a foreign kid. He'd been American growing up in a foreign country. He had traveled back in high school without his mom to Hawaii. He was biracial; he was certainly identified as someone who was black and African American. There were very few people like him in Hawaii. He had moved around a lot, and he just had the experience of being an outsider. ... For the work we were doing, people were poor; people had faced racial discrimination. They're certainly outsiders. So Barack used his own experience of being an outsider ... to identify with other people. ... And he was reflective. So that was the first thing.

The second thing is he was very idealistic. What Barack really wanted, I thought at the time, was to be a civil rights organizer. ... He had been inspired by the civil rights movement and by Dr. [Martin Luther] King in particular. That sort of inspiration, idealism, was particularly powerful for a young man who was half African and who was trying to figure out how to put the various pieces of his identity together.

And finally -- and this is true of him today -- he was very hungry to learn. He really took the job to learn how to do this kind of grassroots work. And what he did in the interview, which is what I always would look for, is he sort of turned it around on me. I mean, in addition to my asking him a bunch of questions, he wouldn't let me get out of there without [his] asking me a bunch of questions. ... His questions were really pointed toward what would he learn, could we teach him anything. ...

How would a kid like him at that point, 24, and with his interests, be drawn to a city run by Harold Washington, [Chicago's first black mayor]?

I want to be clear, because people get this wrong: Barack was not interested in electoral politics. And his first experience with elected officials in Chicago, if he was interested, would have probably drummed that out of him, because there [were] a lot of things to make you cynical about elected officials in the city of Chicago. ...

I think that Harold Washington made it clear to people that Chicago had a major black community. I don't know that Barack knew the data, but in fact, the largest single black community in the United States was the one he came to work in, the South Side of Chicago, almost a million people. ... And I think that the fact that Chicago had elected an African American mayor in Harold Washington sort of emphasized with Barack that he was coming to a city where blacks were a major presence and had some significance.

And when he writes about this period of time, he's struggling to figure out his identity in a lot of ways. Did that come through?

... Certainly he's figuring out how he proceeds with all his diversity. I mean, Barack not only is racially diverse, but he's able to hold different ideas together. But the world doesn't always do as well as he does. And so where does he fit in?

When people usually ask about figuring out his identity, they usually start with Dreams [From] My Father and the racial issue. What was happening at that time, ... he was having conversations with his half brother and sister who had come to the States as graduate students, so for the first time he was learning something about his father, and that was very important to him. ...

How introspective was this guy?

... When he first got to Chicago, his job was to learn to listen. And he's a naturally good listener. He would go out with me, and we'd do six or seven conversations a day. He'd watch me, and then I'd watch him. In those conversations, he'd be looking for narrative. And very quickly he was out on his own, just talking to people, day after day. Then at the end of the day or late in the evening, he'd come home, and he'd take his notes ... and then just put it together: How do these things connect? How do these people connect to each other? Who are they? What are some of their aspirations? What are they facing in the community?

So he's doing that for the people he's working with. And of course when you do that for other people, you naturally begin to do it for yourself in a very systematic way. So he was linking narrative to community to power. That was his job. And in doing so, naturally, whatever skills he learned doing that, he turned on himself. ... It was a very significant period of growth, I think, for him, his two years in Chicago.

And part of the lesson, I suppose, in becoming a good community organizer is to figure out how one attains power. What are some of the lessons that he had to learn about power and how one attains it?

I think a lot of that was learned later in his electoral career as a politician. But certainly what he learned is that what the stated reasons for people doing things were not necessarily the actual reasons. ... Barack came to Chicago very idealistic. Part of our job was to make him more practical. He left idealistic, but he left with a strong streak of practicality; that if you're not practical, you don't do anybody any favors. ...

The other lesson he needs to learn -- I forget the expression -- but it's something like, you work in a world as it is, not as you [would like it to be].

Well, that's interesting, because Barack has turned that on its head. One of the things that I think it's important to understand about Barack's organizing career is that he was sort of a hybrid organizer. He was [a Saul] Alinsky organizer, ... but he also was a civil rights organizer. The difference is that the civil rights organizer organizes a movement based on idealism, and the Alinsky organizer talks about self-interest. ... And what you would learn from that is that: Don't pretend the world as it is is the world as you would like it to be. Get realistic.

Well, in this [presidential] campaign, Barack has used the phrase, and what he said is that you can take the world as it is and make it the world as we would like it to be. And the campaign has been run, to a very large degree, on appealing to people's aspirations, their hopes, not simply their naked self-interest. ...

How did you first hear about [the Rev.] Jeremiah Wright?

Barack is meeting lots of pastors, and he's getting to know the church. He would have to go to lots of services on Sunday. One way to get the pastor to feel good about you is to show up at church on Sunday, and you get introduced to the congregation. So he would write up in his reports, and we would talk about them and who they were and what they were doing.

And how was Wright viewed at that point?

Well, Trinity is a very activist congregation, and on local issues, they've done a wonderful job. ... Most of all, they do wonderful work with youth, and that was always an attraction to Barack. Barack clearly perceived that young people are at risk in these kinds of communities. And Trinity's work on the self-esteem of young people, getting the kids to not defeat themselves, to take their studies seriously, not to accept the image that society might offer them as young black kids but to understand their potential and self-esteem, not to depend on the easy way but to work hard. ...

Pastors were absolutely essential to the work that he was doing. But he's written and other people have written about the fact that it wasn't easy. When he first got there, he was sort of questioned as being the outsider. What was the problem that he encountered, and how did he start dealing with that?

There is a tendency of people to protect their turf, so both local politicians and local pastors -- who can act like politicians -- were threatened by Barack organizing something else in their community. And he had to convince them that this something else was something that was for them and not just in competition with them.

... He [was] called a pawn of Jews and Catholics, certainly an outsider. This whole issue of "Is he black enough?" began to arise, and other scurrilous kinds of things. But the source of that were people being threatened by the loss of their little power base and also by change. And we see that today. I mean, Barack has been threatening to some people, leaders in the black community who have developed a certain way of doing things. And now Barack has challenged all of that in terms of how we move forward with race relations.

Explain that, the whole [Rev.] Jesse Jackson thing. ... What's your perception of that, what he represents compared to what the old style [of] black politics represented? Why is that an important issue to understand?

I don't want to answer that question without going back to the beginning, which is, just briefly, [Dr. Martin Luther] King. And King often talked about forming the beloved community. ... King's issue wasn't to get black people their piece of the pie, but rather it was to build one community where we would all be treated equally and be affirming of each other. And that ... inspired Barack. ...

Barack had had this experience of being part of a large black middle-class community in Chicago and seeing people succeed. Michelle and he, for example, neither needed any help at all to get into university. She went to Princeton and Harvard and excelled from a very modest background ... by hard work and by what her parents taught her. And so the affirmative action as it was had reached its limits. But it had been [the] bread and butter for years of a number of leaders, [probably] including Rev. Jackson.

And Barack comes along and says that it's no longer race, but rather it's just getting equal access to the starting line. Class and income and who your parents were -- all these things count. We need to stop dividing people, find ways to talk about them together. And if we do that, not only will African Americans do better, but everyone will do better together. And that's the kind of conversation we need to have if we're going to move forward now. ...

That's not where the issues and the leadership of the black community had been. So that was very threatening, and behind his back, people might call him names. But it was where the community was. ...

But less threatening to a white voter or white middle-class [voters], therefore having the chance to be a transitional figure.

Well, all this is filled with irony and humor. People who are affluent, who have worked their way up in life and achieved something, whatever their race, whether Hispanic or black or white, identify with Barack. He's very much one of them. He's someone who started from modest means and has met tremendous success. ...

But his policies are geared toward stopping the redistribution of wealth toward the rich and being compassionate for the poor. So he gets people's support who have less money and less status based on the fact that his program is one of not putting them at the bottom of the ladder anymore. ...

Back to the churches for a second. ... Did he understand that in fact he needed to become more involved with the community and with the churches?

An organizer has to keep some distance from the community. That's what we were taught -- [at] least a community organizer. Civil rights organizers, on the other hand, would be very much of the community and from the community. And personally what Barack found in Chicago was a home. From the time he got here, people received him very graciously. He was a skinny young man, and in some of the communities he worked, there were a lot of single moms, single grandmothers, and they wanted to take him in and feed him and fatten him up. He was an eligible young man. They wanted to introduce him to their daughters and to their granddaughters. ...

I think that a lot of what happened in Chicago was taking the theoretical and the book knowledge and making it real. Barack knew that the church had sustained African Americans from the very beginning; that when there was no place else to turn, that's where they would turn for hope. ... So Barack understood that this was the central institution where people gathered for community and for justice and when they were in trouble, either collectively or personally, to find God. ... But it was somewhat academic for him. He had to relate to it personally. ...

... I don't think this thing works itself out until he meets Michelle. He's not really part of the congregation at Trinity until he's moving toward a family. ...

When do you see the first spark of interest in electoral politics?

I don't really know he's going to go there until he tells me he's leaving organizing; he's going to go to law school. But when he tells me that, he tells me why, and it makes sense: what he wanted to see was large-scale change, and community organizing changes small issues in people's lives, and we transform people's lives in terms of teaching them skills and giving them hope they didn't have before. But it structurally was not going to change racial discrimination; it was not going to change poverty in the United States. There simply would not be enough power there. That [change] would only come through electoral politics. ...

Why did he think he needed the law degree from Harvard?

Barack was part of ... a very grassroots world, the world of the streets, so he understood that part of the world. But you also as president have to deal with the wealthy and powerful. ... Barack didn't have that experience. ... He had the experience of being an outsider. He didn't have the connectedness to the levels of public policy and academia and government that other people might have had. And to do that, he needed to connect with one of the major universities, and law school made a lot of sense to him. ...

... The second reason that he gave me when he told me he was leaving -- and understand, we're at Harvard at the time. We're attending a conference on the black church, which is sponsored by the Harvard Divinity School, and we're walking around the campus. He was just getting to know his father's biography in a more detailed way. I mean, his mom really wasn't in touch with his father. ... But his half brother and half sibs were beginning to come over to the States and to Europe to visit, to go to graduate school. ...

And the story as he understood it was that his dad had been overly idealistic and not practical. They had fallen on the outside of the government in Kenya, and not only had he been ineffective at dealing with his own ideals, but he ended up ... destitute financially. And although Barack didn't have much interest in wealth, he had a strong interest in having a secure income to marry and raise a family. He did not want to follow in his father's footsteps. He wanted to be more practical in his choices and more practical in terms of how he might bring change to the country. So his perception of who his father was figured in that. ...

When he comes back from Harvard, how is he different? Has he changed?

Remember, he doesn't go off to Harvard and disappear. Every vacation is spent in Chicago. He's always coming back here. This is his home now, and more so once he meets Michelle. ...

You know, he's very much the same person, with the exception of probably meeting Michelle and moving into that phase of his life. His roots begin to sink much deeper. ... He becomes anchored in a new way in marriage and with those kids. And he's able to move out into the world with a lot more confidence and a lot more perspective, because [he] married a woman who doesn't buy into everything he says, who will challenge him in a variety of ways. And that's very healthy. ...

Let's talk a little bit about the congressional [race against Bobby Rush]. ... What are the lessons learned when he loses?

... One is that Barack doesn't do well with ethnic politics. You know, you're running in an Italian district. Who's more Italian, or who's more Jewish, or who's more Irish, or who's more black? He does not do well with that. Barack's gift to the world is diversity and being able to live in different worlds at the same time, different kinds of people.

And here he is trying to hone himself into the representative of the black community. He moves from Hyde Park, which is a much more racially diverse Senate district into a much more black congressional district. He loses doing ethnic politics; he does badly with it. And he also gets caught in some of the narrow, self-interested kinds of local politics that will happen in that kind of race. ... He's just stronger in a larger arena. He's weaker in that small arena. He's not weak one on one, but the more self-interested and narrow things become, the more he has to turn himself inside out in order to make that appeal. And he simply wasn't good at it.

What is your take on him? Every two years basically, he was jumping to the next large step on the ladder toward amazing power. Where does he get that from?

I think we read that back into the timeline, rather than it being the reality. When Barack returned to Chicago, it was to eventually run for the United States Congress. I mean, that was clearly the position that he wanted and he aspired to. And if part of the road to that was working in the state Senate, that was part of it. ... The jump to the Senate wasn't something he orchestrated. It was thrust upon him because there was nothing else left. Politically his back was to the wall, and if he was going to go anywhere, it would have to be to the U.S. Senate as a major public figure.

But once he begins to go to the Senate, ... it isn't everything that Barack planned. It's things that happened to Barack, and he was able to step up and respond to them. And the presidential race, well, Lord knows he was worried about being elected to the Senate, not president of the United States. And then he gets invited to give the speech at the Democratic convention. And suddenly I walk into a supermarket, and half of the magazines -- and it doesn't matter what they're dealing with; maybe, for all I know, he was on Field & Stream -- have Barack's picture on it. He becomes a media phenomenon.

What does he do with that? Does he lose himself? It's very easy when you haven't been famous and suddenly you're being fawned after to kind of lose perspective. He handles that very well. He keeps his feet on the ground. And people say, "You should run for president of the United States." And he probably laughs. And then people who are close to him and respect him say: "You need to run for president of the United States. You can win. We need to move out of the national nightmare we're in."

So when he takes on this next role that he's always taking on, and the presidential role, does he see it as opportunity or obligation? How does he view it?

I can just say what I know of Barack, and this is [that the] largest influence on Barack is his mother, and his mother imbued him with a strong sense of achievement, that he should be the best at whatever he does. But she also imbued him with a strong sense of service. This is a woman who, when I met Barack, was in Bangladesh developing microeconomic lending programs so women could have spinning wheels in Bangladesh. ...

Nobody runs for president of the United States unless they're ambitious. Anybody who thinks otherwise is silly. And Barack does want to be the best. He wants to achieve personally, but he's also got this strong, strong sense of service to others. And so they coexist in this career. ...

When you look back on it, at that young man that you sat with in the diner in New York City when he was 24 years old, and what you see now, what is your opinion of the evolution that he's gone through?

He's very much the same person, but he's taken these little lessons of organizing in Chicago and he's transferred them to a national and now an international stage. What an organizer does is take people who don't see eye to eye, who may not even like each other, and get them to work together. Well, the underlying theme of this campaign is that if we can't do that domestically, we're in gridlock. [If] we can't do that internationally, our future is in jeopardy.

... He was always willing to challenge powerful people, but he was never confrontational in doing it. He was a very polite young man. So this thing about disagreeing without being disagreeable, that was stuff he honed in Chicago and he believes in, that there's no reason to tear somebody down, even when you're in conflict with them. He's very much the same person that he was, but clearly his skills, the people he has to deal with, that's increased exponentially. And the reason I think he's done well with this is one more characteristic he had in those days, [of] course, that he is a quick learner. ...

When was the last time you talked to him?

It's been a long time.

Doesn't call you for advice anymore?

He hasn't called me for advice for years -- nor should he.