JUAN GONZALEZ: Senator Barack Obama is back in Chicago after his overseas trip. We turn now to the story of how the senator from Illinois and the presumptive democratic presidential nominee was shaped by his years in Chicago and how he navigated the tough world of Chicago politics.

Ryan Lizza is the Washington correspondent for The New Yorker magazine. His latest article traces Obama’s political rise in Chicago. It’s called “Making It: How Chicago Shaped Obama.” He joins me now from Washington, D.C.

Welcome to Democracy Now!

RYAN LIZZA: Hey, thank you, Juan. It’s a pleasure to be here.

JUAN GONZALEZ: Well, Ryan, you had a fascinating article in The New Yorker magazine. It, to some degree, was overshadowed by the front-page cartoon that got all the attention.

RYAN LIZZA: Yeah.

JUAN GONZALEZ: But it really was one of the most in-depth looks I’ve seen at the rise of Barack Obama. And we’d like to spend time going in detail into that article and for you to tell us a little bit about how it was that, when he gets there — I think it was 1985 — he begins to — initially as a community organizer.

RYAN LIZZA: Yes.

JUAN GONZALEZ: Could you tell us a little bit about his — because he often refers to that experience in his speeches, but it was really a pretty short experience of about three years. Could you talk about what he was doing as a community organizer in Chicago?

RYAN LIZZA: Yeah. So, by 1985, he had graduated from Columbia University. And Obama had this sort of vague sense, as he writes about very eloquently in his book, Dreams from My Father — he had this vague sense that he wanted to go work in predominantly African American communities and sort of, you know,give something back. He had gone through a — I mean, it’s probably not much of an exaggeration to call it an identity crisis, growing up in Hawaii, a very multicultural place, with a white mom and a Kenyan dad, who had left him. And he was basically looking for a more authentic African American experience. I think that’s what drew him to Chicago.

And now, why Chicago, of all places in America? Chicago, you know, is — some describe as the capital of black America. And I think he was really drawn to that place. You know, it’s where Jesse Jackson is based. It’s where Farrakhan is based. It’s the sort of capital of black thought in America. And I think that’s one reason he wanted to go there.

The other reason is, it’s one of the few places where he was offered a job. And there were a few guys — one of them was named Jerry Kellman, a white, Jewish — and they were working in the inner city in Chicago, trying to organize the South Side, the Far South Side of Chicago, predominantly black, to — basically for things like job centers, and they were basically dealing with some plant closings. There were some steel plants that had closed outside Chicago and in Indiana that had really devastated the area. And so, these guys were looking — and they were having some trouble organizing in — on the South Side of Chicago, and they were specifically looking for an African American organizer to help them. And Obama applies for this job, and he gets it, and he moves to Chicago in 1985. That’s a long run-up to explain sort of where he was coming from and what brought him there.

When he gets there, what he does for about two-and-a-half, three years is work through the local churches on the South Side, which in a sense are all sort of independent operators. They weren’t working together. So one of the big challenges for Obama and the organizers he was working with was to get the Baptist minister on one street and, you know, maybe the Catholic priest on another street to start to get to know each other and work together to tackle some of these common problems. And so, a lot of what he did was go around to the churches, talking to the church leadership, and finding out what these guys had in common and how they could come together under an umbrella organization to deal with some of the problems from these steel plants closing.

At the same time, Juan, what’s happening in Chicago is a real — Chicago from '85 to ’88, the period when Obama was there, when he was first there, is a really fascinating, tumultuous political world. Harold Washington is the mayor. He's the first African American mayor in Chicago history, the first and the only one. And just when Harold Washington was getting his mayoral office organized in 1987 — he was elected to his second term — he drops dead of a heart attack. And then there was a very tumultuous period after that to find a successor to Harold Washington. Anyway, the point being that Obama was sort of watching real gritty urban politics up close, and it was something that, I think, stuck with him later in life.

So there are two experiences, I guess, in the ’80s. The one is the on-the-ground organizing he’s learning and the concepts he’s learning as an organizer. And the second is he’s watching the first African American mayor of Chicago deal with trying to run that city, and he also sort of watched this grand white-black coalition that Mayor Washington put together then completely fragment and fall apart after his death. So I think those are the sort of two main things he’s watching in the ’80s.

JUAN GONZALEZ: Now, he apparently doesn’t have a whole lot of success with the community organizing and eventually decides to go to Harvard Law School and then returns to Chicago.

RYAN LIZZA: Yeah.

JUAN GONZALEZ: But now, as your article lays out, he really has a bigger plan in mind when he returns to Chicago, and he deliberately goes not to the South Side, but to another neighborhood of Chicago, to settle in and to build political allies. Could you talk about that period?

RYAN LIZZA: Yeah, no, by the time he finishes Harvard Law School in 1991, he’s already telling friends that he wants to return to Chicago and get into politics. He had realized that community organizing was not an effective way to deal with the problems he saw. He wasn’t all that successful at it. The problems were too entrenched to really make much of a difference, as he once told me in an interview.

And so he settles in Hyde Park. Now, Hyde Park — let me just correct you — Hyde Park is on — it’s on the South Side of Chicago. It’s sort of an island in Chicago. It’s integrated, multicultural. The University of Chicago is this sort of anchor of Hyde Park. And then the surrounding area is filled with academics and students, and it’s a very progressive, integrated environment, like a lot of college towns. You know, you might compare it to Berkeley, California or Madison.

And he starts doing a couple of things. One, he meets his wife, and he gets married. Two, he joins a law firm, and the law firm that he decided to join was very much a political statement. He joined the firm that was in opposition to the longtime ruling family of Chicago, the Daleys. After Harold Washington died in — by 1989, Richard Daley was elected mayor. His father had ruled the city for a few decades, from — let me just get this date right — from the ’50s through the late ’70s. In 1989, his father was gone — excuse me, by the late ’70s his father was gone, but by 1989, a Daley is back in power. Obama joins a law firm that is sort of defined by its opposition to the Daley political machine. So, in other words, he was making a sort of a political statement.

And it’s about this time that he starts to sort of look around for an office to run for, and that happens in 1995. He gets his first chance to run for office. And do you want me to — Juan, do we have enough time to sort of tell that story of his first run?

JUAN GONZALEZ: I think it’s — yes, it is critical, in terms of being able to understand how he forms his political vision, yes.

RYAN LIZZA: Yeah. So, what happens, it’s very interesting. He — 1995, which, if you think about it, is really not all that long ago, there’s a woman named Alice Palmer, and Alice Palmer is a longtime local community leader, an education expert, someone with a lot of ties to the African American leadership of Chicago. Her husband, a guy named Buzz Palmer, he had actually started a reform group in the notoriously racist Chicago Police Department, a sort of group to sort of — of African American police officers. So, the Palmers were a family who had a lot of ties to the black establishment in Chicago. They were longtime activists, older than Obama.

Alice Palmer decides to run for Congress, and she decides to leave her — excuse me, she decides to leave her State Senate seat. And Obama decides that he’s going to make a run for that State Senate seat, since Alice Palmer is leaving. He starts going around to all of the key Democratic political operators on the South Side of Chicago and lining up support, and eventually he gets the blessing of Alice Palmer herself, and she endorses him as the replacement for her State Senate seat. And she goes off and runs for Congress.

Now, what happens is, she loses her congressional race very badly. She loses the primary to Jesse Jackson, Jr., who holds the seat to this day. She garners only about ten percent of the vote. And she decides that — she has second thoughts, and she decides that now that she’s forced — she’s, you know, looking at being out of politics altogether, she decides she wants her State Senate seat back. And a group of her supporters tell Obama that he now needs to back down, because Alice Palmer, even after she’s endorsed Obama for the seat, she’s going to return and represent the South Side in the State Senate again.

So, Obama is faced with this incredible dilemma: does he back down, does he bow to the support — to Alice Palmer and her supporters or not? And this really split — this just divided the political community on the South Side of Chicago in half. Some of the people who had backed Obama decided to go back to Palmer. Some of Palmer’s old supporters decided to stick with Obama. And there was a lot of pressure on Barack Obama to back down.

And what happens is, Obama decides to stay in the race. And not only does he decide to stay in the race, but he sends some of his political operatives down to the Board of Elections in Chicago to look at the petitions that Alice Palmer used to get on the ballot. They realize they’re filled with irregularities. They challenge these signatures. And Barack Obama gets Alice Palmer and all of his other opponents kicked off the ballot, and he wins his first race unopposed.

JUAN GONZALEZ: Ryan, I just want to say — we’re talking with Ryan Lizza, political correspondent for The New Yorker, about his latest article in The New Yorker about the rise of Barack Obama. You also mention in the article that, by this time, Barack Obama has become very good at cultivating important people —-

RYAN LIZZA: Yes.

JUAN GONZALEZ: —- or people that could help him on his rise in politics. And you mention a former Congress member who talked to you and said that whenever you mentioned an influential or important person in front of Barack Obama, the first thing he wanted to know was how can you arrange for me to meet them. Could you talk about that tendency in him?

RYAN LIZZA: Yeah. This comes up over and over again. I mean, you know, one of the points of this piece is, I wanted to sort of write a political biography of this guy, right? I realized he was not born on stage in 2004, and I wanted to really explain how this guy operates in the sort of messy world of Chicago politics. And I think it’s essential to understanding how he’s gotten where he is.

And Abner Mikva, a former congressman, former federal judge, former White House counsel for Bill Clinton, and also someone from Chicago, he sort of befriended Obama very early on in Chicago and sort of helped him in his earliest years meet people in Chicago. And he talked about Obama as sort of the ultimate networker. And all politicians are networkers. All politicians — all the good ones — are famous for remembering everyone’s name and sort of sussing out who the — where the sort of levers of power are, where the sort of key influentials are. And Obama was absolutely amazing at this.

You know, as a community organizer, one of the skills you learn — I mean, people hear the term “community organizer,” and they think of it as this sort of fuzzy-headed, you know, “Kumbaya” profession. It is not that at all. Community organizing, it’s, you know, best to think of it as labor organizing. This is hard — this is — you’re taught a very hardheaded approach to politics. And one of the things you’re taught is how to do something called power analysis. And this is something that Obama not only learned, but he taught in workshops all the way through the ’90s. And power analysis is about figuring out who’s got power and how to get it for yourself, so — and not necessarily in a crude way, but in a way to effect change.

So, anyway, like you say, Juan, Obama was very shrewd about understanding the power landscape of Chicago, understanding who the influentials were, and being aggressive about meeting them, introducing himself to them and making it known that he was someone who would be running for office and whose support — and sort of laying the groundwork for some of these people to support him down the road.

JUAN GONZALEZ: Now —-

RYAN LIZZA: And that was -— yeah, go ahead.

JUAN GONZALEZ: As he moves forward, obviously, he links up with what you call the Chicago — the independents in Chicago politics —-

RYAN LIZZA: That’s right.

JUAN GONZALEZ: —- or the reformers —-

RYAN LIZZA: Yeah.

JUAN GONZALEZ: —- that included David Axelrod. Could you talk a little bit about his relationship and the development of his long-term, now, relationship with David Axelrod?

RYAN LIZZA: Well, look, to simplify things, you know, you could look at Chicago politics, at least back when Obama first got there, as the independents versus the Daley machine, OK? So the Daley machine ran the town forever. You know, there’s no real Republican Party, so this is all intra-Democratic politics. Where Obama settled in Hyde Park, that was the home base of the independents. These are the guys that had been fighting Daley for years and years and years. By the ’90s, things were a little more scrambled. The son, the younger Daley, was more effective at co-opting some of the independents at reaching out to some of the African American leadership. So the old Daley-versus-the-independents dichotomy breaks down a little bit, but at least in Hyde Park, that’s the way that most of the leading political figures still think.

David Axelrod, interesting —- has an interesting history. He’s the preeminent political consultant in Illinois, and certainly in Chicago no one even comes close. He worked for Harold Washington, the great champion of the independents and the person who represented the independents’ greatest success. However -—

JUAN GONZALEZ: Was originally a Chicago Tribune reporter, wasn’t he, before that?

RYAN LIZZA: Exactly, exactly. He actually went to the University of Chicago, and he then wrote for a small community newspaper in Hyde Park called the Hyde Park Herald, and then he covered politics for the Chicago Tribune, before eventually entering into politics himself, worked for Paul Simon and then Harold Washington. But he then works for the younger Mayor Daley, so Axelrod is very unique, in that he was a top consultant to both Harold Washington and Mayor Daley in the middle of the independents movement and in the middle of the great enemy of the independents, Richard Daley.

So, by the time — so, Axelrod and Obama, in those early years, don’t really know each other. At that point in the early ’90s, Axelrod is a much bigger deal in Chicago politics than Barack Obama is, and they don’t really link up until about 2002, when Obama decides to run for the US Senate. And that was an incredible coup for Obama to get Axelrod on his side. It was a big multi-candidate primary. There were a lot of tempting — there was one wealthy candidate in there that Axelrod thought about working for. But eventually Obama lands Axelrod, and just by the fact that he had this sort of pre-eminent political consultant, it sent a signal to a lot of the donors and a lot of the political elite in Chicago that Barack Obama was a serious Senate candidate.

JUAN GONZALEZ: Now, even before he hooks up with Axelrod, though, he makes his decision to run against Bobby Rush for the House of Representatives —-

RYAN LIZZA: Yeah, in 2000.

JUAN GONZALEZ: —- and also then, at that point, according to your article, realizes where his major base of support is —-

RYAN LIZZA: Yeah.

JUAN GONZALEZ: —- that it’s not necessarily in the African American community of Chicago at that time.

RYAN LIZZA: Yes. That — you know, the 2000 race, I mean, the more I studied that race, the more I realized that that was the great turning point in Barack Obama’s career. You know, and a lot of politicians at Obama’s level have at least one loss that teaches them a lot. George W. Bush had a congressional loss in Texas, where he was sort of identified as the outsider and not an authentic country boy, and he never made that mistake again. Bill Clinton had a devastating loss in Arkansas.

Anyway, so the point is, one of the things he learned in that 2000 race against Bobby Rush, who’s a former Black Panther and a real icon in the black community in Chicago, I think he — it was a very tough race. There was a lot of, you know, “Barack Obama, you’re not black enough” accusations thrown at him. And I think he came out of that race thinking that his natural coalition was different than what was in — than a strictly majority African American congressional district. He had a lot of — he had a real tough time winning over the African Americans in that race. I mean, and he got pummeled. I think he lost by thirty-something points. And at that time, he’s doing a lot of fundraising among what they call in Chicago the lakefront liberals, a lot of wealthy whites north of Hyde Park. And I think he started to realize that he had this sort of appeal to people beyond just his South Side base, and at the very least, that if he could put a coalition of sort of black, white, liberal coalition together, that that would be a sort of natural base for him.

JUAN GONZALEZ: And eventually, then, he’s able to get his Senate district redrawn —-

RYAN LIZZA: Yes.

JUAN GONZALEZ: —- in the reapportionment to actually include much more of downtown Chicago and the wealthy areas of the city.

RYAN LIZZA: Yeah. You know, he got very lucky. He almost left politics after he lost that race in 2000 to Bobby Rush. But everything after that turns his way. The Democrats in Illinois were — won the right to redistrict the state, and like all Democrats in Illinois, Obama was deeply involved with the redrawing of his own district. In fact, one day in the spring of 2001, he sat down at a computer with sophisticated mapping software and began the process of redrawing his own district.

And his district changed in fundamental ways after that. He used to represent just an area in the south of Chicago that went east to west. His district changed; it now pointed north — it was a north-to-south district — and it included a huge chunk of downtown Chicago, including the famous Loop, which is the big business district; the Gold Coast; all — almost all of the Chicago Lakefront. He represented now all the museums, all the finest shopping areas of downtown Chicago, as well as his original Hyde Park base. So it was a very, very different district. It became whiter. It became wealthier. It became more white-collar. It became more Jewish. And it had one of the highest concentrations of Republicans in Chicago. And the folks that lived and worked in that district now would be the important donors for his US Senate campaign that started — that he started to run for in 2002. So it was a big dramatic change, and that redistricting really was a huge turning point in Obama’s political career.

The other thing that it did, besides the fact that his constituents now were so much different, the overall goal of redistricting in Illinois was to take back the State Senate for the Democrats. They gerrymandered the state, and they accomplished that in 2002. So, after 2002, Barack Obama, who had been a state senator since January of 1997 in the minority, where he couldn’t get much done, he’s now a state senator in the majority. And that allowed him to do — to actually get some things passed and get all of the issues — and get all of the things passed that he would then use as a platform for his 2004 Senate campaign. So that redistricting was incredibly important to his political career. I think you could make an argument that without that redistricting, he may not have been a real contender in that US Senate race.

JUAN GONZALEZ: And finally, Ryan Lizza, I’d like to talk a little bit about that famous antiwar rally —-

RYAN LIZZA: Yeah.

JUAN GONZALEZ: —- where Obama constantly refers to when he first took a stand against the Iraq — or the looming possibility of a war in Iraq, while other political candidates did not. But you talk about the rally, and specifically what he said at that rally and how calculated he was even then in the political message he was sending out.

RYAN LIZZA: Look, you have to remember, Obama was from Hyde Park. It’s one the most liberal State Senate districts in Illinois. He could have been as left-wing, as liberal as he wanted. But he wasn’t. He was always — and, you know, there are various reasons he wasn’t. I think genuinely he’s — he was a little to the right of some of his constituents. But I also believe that he had his eye on higher office, and he was careful not to be pigeonholed as too far out on the left.

And his speech at the antiwar rally is a good example of that. And just like redistricting, I think you can argue that if he hadn’t opposed the war in Iraq, he would not have been a plausible presidential candidate, because that was the key distinction, of course, with Hillary Clinton. But the speech was not a — what you might call a typical antiwar speech. He started off by talking about wars that he supported: the Civil War — he talked in almost glorious terms about the Civil War and World War II. Now, nobody opposes the Civil War and World War II, so they’re not exactly the riskiest things to support. But he was in front of a pretty, you know, partially pacifist crowd, and it is an antiwar rally, and he was very careful to point out that — where he disagreed with folks in that crowd. In other words, he was trying to push off the left a little bit. He was trying not to be defined as strictly an antiwar candidate.

At the same time, he made a — if you read it today, it still stands up very well. He made a very powerful case against the Iraq war at a time when a lot of Democrats weren’t doing that. But there were certainly some politics in mind. And if you talk to some of the people who were in that audience that day, one of the common things you hear is, “Wow, this guy is not just talking to us, he’s talking to either some statewide or national crowd. This speech seems pointed for the — seems more like for the history books than just for us here at this antiwar rally.” And this comes up throughout Obama’s political history. He often had his eye on the next rung of the ladder, if you know what I mean.

JUAN GONZALEZ: Well, Ryan Lizza, I want to thank you very much for being with us. Ryan Lizza is the political correspondent for The New Yorker magazine. His article is called “Making It: How Chicago Shaped Obama.” It’s a fascinating read.