• Highlights from this interview
• Why youth are drawn to Obama's message
• The African American politics Obama confronted in Chicago
• The tactics and hurdles during Obama's early political years
• How politics has changed for a new generation of African Americans

Take me to Obama's 2004 Democratic convention speech.

That is a speech that he had given, in large measure, in the 2000 congressional run. It was a very familiar speech to me, having been his deputy campaign manager on the congressional race. There were some new wrinkles, obviously, about his more biographical information and the stuff about the red states and the blue states. ...

... I was literally watching it on television and, like, reciting it. And I was calling a friend of mine who helped to organize his clergy committee in 2000. Both of us were cracking up that this was the same speech that he used to give to crowds of, like, 10 people or in some church on the South Side, where no one knew how to pronounce his name and they were just meeting him for the first time. ...

Were you surprised by the success of the speech?

No. Having worked with Barack for as long as I did, I knew that if Barack had the right opportunity to show who he is, and his vision, he would move the country. He had been moving the crowd -- to use a sort of hip-hop expression -- for a long time. And it was just a matter of having the right venue, the right message, and being in the right time.

Our politics have been focused on narrow strips of the electorate and pushing the right issues to motivate those folks, as opposed to a broader message and theme about the notion of an American identity and the notion of a shared responsibility, our sense of a collective identity and a collective responsibility and an individual responsibility to each other. And I think people were hungry for that.

What were your expectations at that moment for what he would be doing in the near future and how far he would go?

There was a lot of debate. There were people who were thinking, at that exact moment, he should be running for president. That night, when I saw the speech, I can't recall thinking, OK, in 2008 he runs for president, but I knew that he was on his way.

To me, it was a validation of the work and the hopes that many of us had placed on him very early on, when it wasn't clear that he would even be on that stage. I can remember times when he ran for Congress and when he was a state senator, you struggled to get the press to cover your press events; people didn't know who he was. So it was a great moment.

When did you first meet him? How did you start working with him?

I met him in the fall of 1995. I met him at his campaign kickoff for state senator, which was at the Ramada Inn at [Lake Shore] in Hyde Park. It was also the place where Harold Washington declared his candidacy for mayor in 1982. So it was sort of a place that has certain political resonance to independents on the South Side of Chicago, or at least used to. ...

I'd just turned 22. I was working for a small social service agency on the South Side, trying to sort things out. Next thing I knew, I was knocking on doors for him, volunteering, getting my friends up on Saturday mornings. There was like a crew of us, and we would go knock on doors for him and circulate petitions.

When I was in graduate school, I prevailed upon him to hire me to work in his district office, answering phones, stuffing envelopes, constituent service-kind of things.

There are a lot of people who talk about his ability to bring in the youth vote in a way that has never been seen. But you're saying that really, this was something he had the ability to do from the beginning.

I can't speak for everyone. I can speak for myself when I was 22. I was born, obviously, after the modern civil rights movement sort of had ended. There wasn't anything to really be involved in that you felt had the opportunity or the possibility of changing the world in which you lived in a sort of structural and meaningful sense.

And what Barack has the ability to do, and has always had the ability to do, is to take what could be seen as sort of your bread-and-butter political speech or political campaign and transform it into a broader movement and conversation about what kind of society we want to live in, what are our responsibilities to each other, and creating the sense that you could be in a part of changing history. ...

There are a lot of people that talk a lot about the generational differences, especially in African American politicians in Chicago. When you look at Obama, do you see this as sort of the torch being passed to a next generation? How do you view the differences in style, in emphasis, in focus of Obama, which has caused him a lot of trouble with a lot of older black politicians all throughout his career?

... I think a lot of times in African American politics, the politics tend to be about symbols as opposed to being tied to a concrete reality. ... He was focused on real, substantive issues, as opposed to "We're going to fly a red, black and green flag, and we're going to use some Swahili words, and I'm going to wear dreadlocks, and you're going to wear a garb, and we're going to have a cultural discussion." But this was really about, how do we change our society? ...

My mother is a black nationalist, so I come from a nationalist background. I got dragged to Kwanzaa celebrations when nobody went to Kwanzaa celebrations, and a lot of guys walking around in black leather jackets and big afros and black sunglasses. I grew up with all of that. And it always felt, to me, that it was more about creating a psychological defense against white racism than necessarily a political program to change the structural barriers and obstacles to the full inclusion of African Americans into American society. And so that's what I wanted to participate in. And that's what I felt Barack Obama was about. ...

I think there are specific sorts of data points where that was a very real issue. So if you look at 1995 and 1996, when Alice Palmer decides that she wants her state Senate seat, ... and then you look at [Obama's] run against [Congressman and former Black Panther] Bobby Rush in 2000, ... those are very specific data points where there was certainly conflict with the older generation. ...

So Palmer doesn't do so hot in the [1996] congressional race. What happens? Do you remember anything? Were you involved in any of the discussions or hearing that there was something going on, that people were coming to talk to Obama and trying to get him to withdraw?

Yes, I was aware of that. And the guy who was really in charge of the petition challenge was Ron Davis, and I was one of Ron Davis' young acolytes. ... And he was like: "Well, Alice is going to get back in this thing. She's got people out on the streets circulating petitions. We're going to have to be ready."

And what I recall about that time is that Barack wasn't thrilled about it. He didn't relish the idea of having to fight Alice Palmer. But he was also someone who took integrity very seriously. "Look, here was the agreement, you know. [Editors' Note: Read differing views on this agreement from the Chicago Reader and the Chicago Tribune.] I've gone out and raised money, opened up an office, recruited people, put my name out there. And I'm supposed to take that back because you now want to change the agreement we already had? That just doesn't make a lot of sense."

And I thought it was profoundly unfair, and I thought it was wrong. ... I wanted to be part of an effort to defend Barack, so I went down to his office and looked at the petition, and late into the night checked them against the key book and did what I had to do. ...

So he wins. He goes to Springfield. What are some of the problems that he encounters, as far as some of the older --

I think the perception was that he was on some level disrespectful to older leaders by not accommodating Alice Palmer's request [to bow out of the race]. Alice Palmer was a beloved activist in some of the progressive and nationalist circles. Those folks were not pleased with what happened. And she was well liked by her colleagues. ...

But you know what? These seats are not entitlements. There are rules and procedures. And so I personally didn't really get it. I still don't get it. And so I think that that established [him], and it sort of put him on the radar screen, as somebody who was going to follow his own path, and not going to be intimidated or knuckled under by other folks. ...

What's the run for Congress [against incumbent Bobby Rush] about? And what high wall does he have to climb once he goes back down that trail?

Well, to set the context, Bobby Rush had run for mayor in 1999, and that mayoral bid did not go particularly well. And I think there was a feeling that Bobby Rush could be beaten in a Democratic primary. ...

... Sometimes the only way that you can advance is to make it clear to people that you want to be advanced, and one of the ways that you do that is to run for higher office. ... I think he was looking for ways to move up and to put his name out there, and I think the congressional race was the way to do it. He didn't lose his state Senate seat at the time, so it made a lot of sense, too. ...

So what happened?

Well, we lost badly, 2-to-1. I was the deputy campaign manager and the field director in that race. I think there are a couple of things that went wrong with the race. One, I don't think that we had as fine-tuned a message as we could have had. [Two,] I think that Bobby Rush had some really horrific tragedies happen to him personally that increased his sympathy with the electorate.

His son was shot.

Huey Rich was shot and killed in the winter of 1999. His father also passed in 2000, early in 2000. And then I also think that Barack wasn't well known enough to make the case that you should fire this congressman and give this young guy a shot. You know, Bobby Rush had a longstanding history with the African American community as a member of the Black Panther Party, as a leader in the Harold Washington era, and in like two seconds, Bobby Rush could explain his bona fide[s] to the African American community in a way that it was a little bit more complicated for Barack.

But I think there was a lot of good will that came out of it. There were a lot of people who said: "You know what? I like the kid. I'm not going to vote for him this time, but I like him, and he should keep doing what he's doing." ...

The "not black enough" allegation -- what was going on with that? How dirty did it get?

It was real bad. And there was an article in the Chicago Reader, which is essentially the Chicago version of The Village Voice, where a number of black nationalists and other observers in the African American community made all sorts of allegations about Barack being a tool of Hyde Park and the University of Chicago, which are both code words for both whites and Jews. And there was a lot of that in the race.

But to me, black identity is deployed as a political tool when it is expedient. So when Obama, if you look in 2003, when he's the only credible African American candidate in the U.S. Senate race, and facing white candidates and a Latino, clearly in that context he's black enough to gain the support of the African American community. It's only sort of "blackness" in a relative term. Is anybody black enough? I mean, how black am I, compared to a guy who served with the Black Panther Party? I don't know. ...

Did he also understand, after this race, more about his constituency?

... I think what he ... figured out was that he was going to have to find the right office to run for. It was going to have to be the right time. He was going to have to cultivate other allies and expand his base of allies and networks. I think that he recognized that he put himself out there on the radar for higher office later on. I mean, part of the way it works in Chicago is that you sometimes run for something, you don't get it, but people know that you're somebody who's thinking about something down the road, and it makes you more interesting. ...

What were the steps toward higher office?

There wasn't a direct path. I can remember in 2001, there was a group of Democratic activists that met. Sen. Dick Durbin [D-Ill.] had this group called 200 for 2000, so it was all these young Democratic activists. And another Obama aide by the name of Dan Shomon printed up these buttons that said "Obama Statewide 2002." So there wasn't an office; it was just like "Obama, Something, Statewide 2002." ... And I don't think that the right opportunities aligned themselves in that cycle. So he was patient. Later in 2002 or early 2003, he decides he's going to go for the Senate seat. ...

You just said something a second ago which a lot of people would laugh at, that this is a man who was patient. He seems to have moved up the ladder at an enormously fast pace. Do you see that?

... I don't think that there was a sort of "Ah, this is the moment when it became clear that he was going to be the U.S. senator and then the Democratic presidential nominee in 2008," or some plan in some secret room in Hyde Park someplace where all this was plotted out. But Barack is and was an extremely talented politician, legislator, thinker. And the question was not "if"; the question was "when, how and for what?" And so it was about answering those questions and having the right alignment of support early on for an office that would make sense. And, you know, I think that that's where the U.S. Senate race becomes very important. ...

Another important thing happened in 2001, which is kind of behind closed doors.

The map?

The map. It's written about in The New Yorker thing. But it is interesting.

Not the whole story, though.

Tell me the whole story. Why was that important? Because what it does is it defines his future in a lot of ways.

I think it defines his future in that the Democrats end up with the majority in the Senate and are now in a position to drive a legislative agenda. ... [M]any of the bills that Barack passes in 2003 were bills and ideas and concepts that he had been talking about or introducing and sitting in the Senate Rules Committee, because the Republicans certainly weren't going to let them see the light of day.

So I think the redistricting is important from the perspective of the broader context of empowering the Senate Democrats and making Emil Jones the president of the Senate and the guy who controls the Rules Committee, the guy who controls the floor, and the guy who can let Barack pass his bills.

For the record, at the time, I was the vice president of programs at the Chicago Urban League. The Urban League and a number of other civil rights organizations worked together in this coalition called the African American Working Group on Reapportionment, and we drew African American districts for Cook County. We drew Barack in that long end district.

We didn't draw those districts to benefit the Democrats, but we were very concerned about how the Republicans had drawn the map in the 1990s. ... We wanted to expand African American political power. ...

OK. There's [a prominent community organizer Saul] Alinsky rule which is sort of interesting in how it defines what he understands, which is, "Operate in the world as it is, not as you would like it to be." Explain that. ...

Well, it's the corollary of "Politics is the art of the possible," right? ... It's very easy to be ideologically pure, but that's not how stuff gets done. You have to see the world as it is, who wants this, why they want it.

I mean, it's part of what community organizers do. It's called a power analysis. ... When you do your analysis, that helps you figure out what actions you're going to take to fix the problem. You have to live in the world as it is and not as you wish it to be. And it's very difficult to do that and not become captive to a cynicism about what can't be changed. And I think what is good about Barack is that he keeps his foot in the world as it is, at the same time while he tries to change the underlying conditions that [make] that political reality a reality.

So what does that mean? Look at what he's done in the gas tax. It would be very easy for him to say: "You know what? I'm with you. We've got to get rid of the gas tax because it's just an unfair burden on American taxpayers who are trying to commute to work, and da da da."

And the reality is, is that we need the gas tax in order to pay for roads. And, you know, the gas tax is not going to provide that much relief. It's a cheap political gimmick. And so instead of just sort of pandering, he's like, "Look, I believe I can make the argument to the American people and engage the American people in a dialogue about this issue, and they will understand what I'm trying to get across." ... And his opposition to the gas tax, at the end of the day, didn't hurt him. His opposition to rolling back the gas tax did not hurt him.

Part of being an organizer, too, is sort of an educative function. And we haven't had, I think, the kind of president in this country who's really sort of educated the American people about difficult issues. ... I think Barack has the potential to be like the next FDR in terms of explaining, in those fireside chats, and really engaging people in real conversation about what the limits of government are, what the responsibilities of government are, what the responsibilities of citizens are to each other and to themselves. And I'm excited about that.

When you were working for him, ... how did he act? Did he go around and sort of teach people how to organize?

I can remember the town hall meetings, where you'd get like 15 people on some Saturday morning in some sort of church basement in a community room. And he would take people's questions very, very seriously. He would say: "Look, here is what I support. Here is what I'd like to do. Here are the obstacles. Here's what I'd like to do to change those obstacles. And here's what I need you to do to help me do that. And let's be honest. This is a very difficult hill for us to climb. Here's what I would measure as sort of a step toward reaching our ultimate objective."

... He would really take the time to have a real conversation with people in these meetings and forums when he knocked on doors about what was really happening. I used to drag him away from people's front stoops, because he would just talk with them. I mean, he would answer their questions, I mean -- and ... there was something honest and real about the interchange and the way he operated.

Explain to me the anger of a [Rev.] Jesse Jackson to Obama.

So here's the way I would understand it, is that if Barack were white, the assumption would be that Barack could not directly appeal to the African American electorate, that he would have to use gatekeepers to secure the African American vote. And in this kind of situation, Barack can appeal directly to the people without a filter, without a gatekeeper. And, in fact, those who used to control, or at least significantly influence, African American political opinion and African American political behavior now find themselves in a situation where Barack, the presidential nominee, has the initiative.

So Jesse Jackson can't go out and criticize Barack Obama for whatever policy differences he may have with him, because he knows that the same constituency that supports him is supporting Barack Obama. So what do you do? I mean, it's difficult. That's my analysis.

What's your view of the theory that [author] Shelby Steele throws out there, that Jackson was all about using white guilt to progress, to push forward an agenda that was necessary, while Obama works on a different level? ...

... What I think Steele has wrong is that Jesse Jackson has a different kind of politics that is more ideologically on the left, that calls for a greater degree of government intervention, and that is much clearer about the need for race-based policies to address problems, and not using white guilt as a problem, but using actual bona fide data that demonstrate the massive structural inequalities between some African Americans and whites in this country.

I think what Barack's strategy is, is to emphasize the common challenges that black and white Americans face. And in the process of addressing these common challenges, whether it's access to health care or unemployment or high fuel prices, or the need for foreign policy that defends the entire country and protects us and makes us safe, you are able to address some of those structural inequalities without highlighting the fact that that's what you're doing. ...

Where are we generationally? This seems to be what some people sort of say is a passing of the torch, racially as well as generationally -- white, black, both. ... Where are we? What does he represent? Where are we going?

I think that what Barack represents, in a very tangible way, and what I think he shows is just how "American" black Americans are. ...

Barack is the promise of the civil rights generation, that if we can get access to high-quality institutions, if we can get into Columbia and Harvard Law and get the opportunity to serve on the Harvard Law Review, that there are outstanding things that we can do. So I don't see it as an "us against them" sort of thing. I see it as, hopefully, a continuation of the arc toward justice that Dr. [Martin Luther] King used to talk about. ...

As a young black politician, how have things changed? I mean, older ones, you know, if you're old and you look at what has changed in the idea of Obama running for president right now, [it] is an amazing fact. When you look at it, how do you see it?

I see it as absolutely amazing. Where I grew up in Warrensville Heights, Ohio, there were concrete barricades that connected the streets in my middle-class African American suburb to the mostly white, at the time, Shaker Heights, Ohio, so that cars couldn't travel between the two communities, except for the major thoroughfares. The high school I went to, there were 20 African American students. I was called "nigger" when I was 15. I have experienced racism in my lifetime.

And so this is very surprising to me. I mean, I thought that maybe I'd be in my 50s or 60s before I would see something like this. My mother was interviewed ... and said, "I never thought, in my lifetime, I would see this." So what it means for me is that my daughter, who is 9 months old, I can legitimately tell her that there's nothing in this world that you can't do. And my parents couldn't tell me that.