MELISSA BLOCK, host:

This is All Things Considered from NPR News. I'm Melissa Block.

MICHELE NORRIS, host:

And I'm Michele Norris. We're going to spend some time over the next two days looking at Barack Obama's experience in Chicago and how that time helped shape him as a politician. Chicago is known as the City of Big Shoulders, famous for its pugilistic politics. That's a point of tremendous pride says Delmarie Cobb, a longtime Chicago political operative.

Ms. DELMARIE COBB (Political Consultant): This is Chicago. And we always say there's a little bit of gangster in everybody who's from Chicago.

NORRIS: But when Obama first stepped on the national stage in his run for the White House, he faced constant questions about his fortitude and his lack of experience in national politics. Is he tough enough? When attacked, will he cower? Or will he fight back and go for the jugular? So common were these questions that a popular New York Times columnist took to calling Obama "O-Bambi."

It's now widely believed that he toughened up in the course of a long nomination battle. But people in Chicago, like Delmarie Cobb who knew Obama long before he became a political star, say he's always had that warrior instinct.

Ms. COBB: You know, I don't think he was naive, by any means. And I think people are beginning to discover that there is nothing naive about him.

NORRIS: Case in point, his first election. It's a story that could well be called the political execution of Alice Palmer. Palmer was a friend and early mentor to Obama when he was working as a grassroots organizer after law school. She was a longtime and popular state senator on Chicago's South Side. In 1996, Palmer decided to make a run for Congress. Alan Dobry is a longtime political activist who lived in Palmer's district. He says Obama was the chosen successor.

Ms. ALAN DOBRY (Democratic Political Activist): Well, if you go to the U.S. Congress from being a state senator, who will replace you? Or are we just going to have some machine thug step in? And she says, no, I have this fine young man named Barack Obama. He seemed to be a more than acceptable replacement for Alice.

NORRIS: But Palmer lost in the primary for that congressional seat and decided that she wanted her old Senate seat after all. Her protege, Obama, would have to step aside. It was a test, a Darwinian dilemma. In order to fulfill his own ambitions, he would have to kill his friend's political career. Obama stood his ground and even went with one step further. Using an aggressive procedural move, he challenged the signatures on Palmer's nominating petitions. And he even went beyond that. He challenged the petitions for all three of his opponents. Now, mind you, it's not unusual for politicians to muscle rivals off the ballot, not in Chicago, explains longtime Chicago Alderman Toni Preckwinkle.

Ms. TONI PRECKWINKLE (4th Ward Alderman, Chicago): It's what you do in Chicago. My view is - and since I've challenged people and challenged people off the ballot - my view is, you know, you're not ready for primetime if you can't get your petitions in order and file them according to the requirements of the law. And if you fail to do that, then, you know, that's your problem.

NORRIS: And there was a problem. It turned out all the opponents had faulty signatures. Back in that '96 race, Alan Dobry was one of the people trying to verify signatures for Obama's campaign

Mr. DOBRY: And we looked at their petitions, and we saw that, Alice, her petitions were circulated by people named Pookie, for instance, who circulated that. We know what that means. It means somebody got a bunch of kids from the local high school to circulate the petition, and they put down the name as Pookie.

NORRIS: Obama's maneuver worked. He knocked all of his opponents off the ballot. He cleared the field and sailed on to an easy victory in the heavily Democratic district. Obama arrived in Chicago as an outsider, a guy who was raised in Hawaii. The move against Palmer proved to Democratic Party insiders that just maybe he had what it took to survive in Chicago, says Laura Washington, a columnist for The Chicago Sun-Times who's covered politics for almost three decades.

Ms. LAURA WASHINGTON (Columnist, Chicago Sun-Times): Chicago is a tough political town, bear-knuckled. Folks fight to get ahead. If he wanted to win, and if he wanted to be received as a tough cookie, he'd have to do what it took. I think that that election was what made his peers finally sit up and take notice. He was nobody until he knocked off Alice Palmer. And his peers, I think, secretly admired his ability to do that, even though some of those folks were supporters of Alice Palmer.

NORRIS: Even though Obama had earned his party's respect, he faced significant challenges. He still had to penetrate a political machine that usually required a hometown pedigree. He had no family connections, no neighborhood network. But he did know a lot about grassroots organizing. And as a student of Chicago politics, he picked up a key lesson. Politicians are as powerful as their patrons. Jerry Kellman knows this well. He hired Obama to come to Chicago and work as a community organizer. And over the years, he watched Obama build his network.

Mr. JERRY KELLMAN (Director, Institute for Spiritual Leadership): Barack is wonderful at finding mentors, but not emotional mentors or mentors to advance his career, but mentors he can learn from. He's just hungry, and he'll attach himself to all kinds of people. Not even people necessarily of status, but anybody who can teach him something.

NORRIS: Notice that Kellman said Obama is wonderful at finding mentors. That's an important detail. Kellman and many others told us that Obama doesn't wait for people to take him under their wing. He's much more assertive, tracking down powerful fundraisers and people that could help him maneuver for key committee assignments in the State Senate.

State Senator EMIL JONES (Democrat, 14th District, Illinois; President, Illinois Senate): Well, my first impression, really, of Barack, he was very intelligent but rather pushy at the time, you know.

NORRIS: That's Emil Jones, president of the Illinois Senate and one of the most powerful figures in Illinois politics. After winning a State Senate seat, Obama quickly pushed his way into Jones' good graces. And when Obama was contemplating a run for the U.S. Senate, he turned to Jones, using a combination of chutzpa and flattery.

State Senator JONES: He came to me, and he said to me, he said, you're the Senate president now. You have a lot of power. I said, what kind of power do you think I have? He said, you have the power to make a United States senator. I said, that sounds good and everything. I said, I had never even thought about it, which I hadn't. I said, if I have that kind of power, do you know of anyone I can make? And he said, me.

NORRIS: Now, this was a very gutsy move for a junior state senator, and a little history will help you understand why. Obama was ambitious, but he was far from a political star in Chicago's largely black South Side, a fact that had been made painfully obvious when Obama challenged incumbent Congressman Bobby Rush in the 2000 Democratic primary and lost badly.

So here was a young politician who couldn't win a congressional seat in his own neighborhood asking one of the state's political kingmakers to back him for a statewide race. Furthermore, Obama wanted Jones to help him leapfrog over a line of more established and much more powerful politicians. Bold, huh?

Well, it turns out, that's exactly what happened. One reason, Jones knew that even though Obama had limited appeal in his district, he had wide appeal beyond Chicago's largely black South Side. And Jones offered this story to make his point. Back when Obama was running for his U.S. Senate seat, Jones was traveling with the candidate in southern Illinois, an area known for being white, rural, and conservative.

State Senator JONES: You know, I'm sitting across the table from this little old, white lady, and she made the most profound statement. She said to me, you know, I'm 84-years-old. I certainly hope I live longer though. This young man - speaking of Barack - is going to be president one day. And I want to be around to vote for him. That was her first time meeting him.

NORRIS: That underscores another important lesson Obama learned in Chicago, the importance of building multiethnic coalitions. South Side black politicians traditionally build bedrock black constituencies by standing up to the white establishment. Obama embraced it. He was eager to lock arms with white leaders in politics and business says Chicago Sun-Times columnist Laura Washington.

Ms. WASHINGTON: When he was a state senator, he was raising money from folks outside his district, which was really unheard of at the time.

NORRIS: How did he get away with that? Because a lot of people view those sort of patrons and benefactors with great suspicion.

Ms. WASHINGTON: I think, at the outset, because he started when he was a state senator, he was so far under the radar no one was paying attention to him. He wasn't perceived as a threat to anyone.

NORRIS: In Obama's case, geography made a difference. His state senate district was in Hyde Park, a multiethnic enclave in the heart of Chicago's black belt. Hyde Park is home to the University of Chicago and much of the city's black elite. Emil Jones knew those financial, intellectual, and social power centers all could help Obama launch a credible Senate bid.

Mr. BEN CALHOUN (Political Reporter, Chicago Public Radio): There is this bubble of Hyde Park where things that aren't politically possible in other parts of the city are politically possible there.

NORRIS: Ben Calhoun is a political reporter with Chicago Public Radio.

Mr. CALHOUN: You don't have to become a precinct captain. You don't have to look for an opportunity to run for state rep and then run for state Senate and then maybe some - you know, decade down the line, run for Congress or the U.S. Senate. He was able to just - not do an end run, but to sort of go through the side door. He, you know, just sort of slipped around the normal ladder that Chicago politics requires people to slowly work their way up.

NORRIS: Hyde Park is an island of independence that seems to be always locked in battle with the Democratic machine that runs the city. Politicians from Hyde Park who dare to cozy up to that machine have a hard time rounding up re-election votes. Obama forged a new path. The more powerful he became, the more he embraced the machine, but very carefully, says Chicago reporter Ben Calhoun.

Mr. CALHOUN: If you look at his relationship with machine politics in Chicago, you see a very careful and well-planned relationship. He made certain alliances. He made certain endorsements. He embraced people when he needed to. But at the end of the day, he also always maintained a certain buffer between regular machine politics. But he only did that by getting to know it and getting to know what that machine wanted and how it worked.

NORRIS: So he didn't get oil on his hands?

Mr. CALHOUN: Exactly.

NORRIS: While we were in Chicago, we talked to many people who helped launch Obama's early career. They're proud of the Democratic nominee and pleased that they share a piece of history. But as to those lessons - how to be tough, how to work the system, how to survive - several people expressed a certain discomfort about how Obama used that Chicago education as a star continued to rise. Hyde Park political activist Alan Dobry.

Mr. DOBRY: I'm afraid he learned to go along. Or as a fellow I know, another committeeman, Bull Jive Taylor, used to say to me, Alan, why don't you go along? It will be so much easier. Everything would be so much smoother. And I think Barack learned to go along. It may get him elected president, but it doesn't make me happy.

NORRIS: Dobry is supporting Obama, but he's not exactly enthusiastic.

Mr. DOBRY: And so I will vote for him, but not - how should I say it? - full out he's the second coming or something, but rather that's the best we can do.

NORRIS: You expected more? Or something different?

Mr. DOBRY: Well, when he started out and we worked very hard for him, I thought we were getting something a little different.

NORRIS: Tomorrow, we'll take a look at how Obama came to Chicago and how he used what he learned as a community organizer to launch his political career. Next week, we'll look at how John McCain's background in Arizona and Washington has shaped who he is today. And, as always, there's more stories about the candidates at npr.org.

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