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Ahead of History-making Speech, Writers Look at Obama’s Career

August 28, 2008 at 6:25 PM EST
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Ahead of Thursday's eagerly-anticipated speech during which Sen. Barack Obama will accept the Democratic nomination and become first black American to lead a major party into the fall elections, a panel of Chicago writers discuss the Illinois senator's career path.
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RAY SUAREZ: We’re joined now by two Chicago writers who’ve long covered Barack Obama.

David Mendell is the author of “Obama: From Promise to Power.” He was a staff writer for the Chicago Tribune for 10 years.

And Laura Washington is a columnist for the Chicago Sun-Times, who’s followed Obama since his days as a political organizer in Chicago in the 1990s.

And, David Mendell, you often hear, even today, that people don’t know Barack Obama. But very few Americans have written two best-selling memoirs by their mid-40s and had you write a biography about him, too.

How come people still say that at this point?

DAVID MENDELL, Author, “Obama: From Promise to Power”: Well, I think he just doesn’t fit neatly into any one demographic. He is a biracial man from Hawaii who was raised in a white family, has spent time in Indonesia, has bounced around the continental United States, went to college in L.A., New York, Boston, and then landed in Chicago.

So he’s a hard character to get your arms around. And I think people don’t have a good sense of what that is, what he is, after that unique biography.

RAY SUAREZ: Even after almost two years of pretty intense scrutiny, Laura?

LAURA WASHINGTON, Chicago Sun-Times: Intense scrutiny, but there’s been an incredible fanfare. He’s been awash in the celebrity that the Republicans have criticized him about.

You go back and think about that day when he announced in Illinois, in Springfield, that freezing cold day, and 17,000 or 18,000 people showed up, and they were crazed with excitement about him. He’s taken on sort of this mythic, iconic stature throughout the country.

So people — and because of that, I think people attach to him whatever their own dreams and whatever their own beliefs are. Some people believe in him because he’s a black man. Some people believe in him because he’s been overseas. Some people believe in him because he’s young. Some people believe in him because he talks about change.

And so everyone thinks he is who they want him to think, but, really, no one knows who he really is.

RAY SUAREZ: Well, David, in your book, you used words like “imperious, mercurial, self-righteous, extraordinarily ambitious.” It seems there’s more to know about this guy in your book.

DAVID MENDELL: Well, yes, those are certainly characteristics he has. He can be a little bit imperious, especially with reporters and those who kind of invade his world. This whole celebrity thing was a very uncomfortable fit for him at the beginning.

As much as he sought it out, as ambitious as he is for both he and Michelle, his wife, it was a — you know, it freaked him out at the beginning. And he’s had a — it’s been a learning curve for him to figure out how to deal with that over this period of time, so…

Chicago has been home base

Laura Washington
Chicago Sun Times
He did, in the sense that he didn't wait his turn. That's why he got beaten so badly by Bobby Rush. Even when he was in Springfield as a state senator, he was running around trying to propose legislation. Imagine that.

RAY SUAREZ: Well, Laura, Chicago has been one of the crucibles of black politics in America, the way it's done. Does he fit into that in, in any sense, from the 60 years since Bill Dawson, the 20 years since Harold Washington?

LAURA WASHINGTON: That's exactly why he went to Chicago. He knew he had high political ambitions when he came to Chicago. He picked the city because of the reform tradition it had, because of the bossism tradition it had, because of a huge black middle class, because of the huge black political class.

He came during the period of the Harold Washington era, where he was the reformer, the person who was fighting city hall, but was fighting city hall after having been part of the political establishment. And he saw that as a model he could follow.

The fact that Harold Washington built a coalition to get elected, Barack Obama's built a different kind of a coalition but, indeed, he's brought together disparate groups of people. And he saw Harold Washington and what was happening in Chicago as a model for that.

RAY SUAREZ: Did he have to rock the boat with the older leaders?

LAURA WASHINGTON: He did, in the sense that he didn't wait his turn. That's why he got beaten so badly by Bobby Rush. Even when he was in Springfield as a state senator, he was running around trying to propose legislation. Imagine that.

That's not done in Springfield. You have the bosses decide what the legislation is going to be, and they tell you where to stand and how to vote.

And here he was. He's pretty much of a policy wonk, and he had a lot of ideas, and he didn't want to wait his turn to propose them. And a lot of people expected him to wait his turn. And that rocked some boats.

RAY SUAREZ: Well, David Mendell, we're also looking at a guy who's about to run for president, or has been running for president, who's never had a tough Republican challenger before.

DAVID MENDELL: That's true. He's never run in a Republican race. He had Alan Keyes and a Republican who dropped in his U.S. Senate race. So he basically spent that whole time just trying not to drop the ball himself.

He used an extraordinary amount of self-discipline, because that race was fraught with peril. There were some sexual allegations on the other side of the ticket there.

But he kept focused and kept plowing ahead steadily. But his ideas and how he would match up against a vigorous Republican challenge, we haven't seen that yet.

LAURA WASHINGTON: You don't see that from anybody in Chicago. Chicago is, of course, a Democratic town. There's one Republican in the entire 50-member city council.

And so I think that's one reason why you haven't seen someone like him or seen a Chicagoan prevail, because they've never been tested that way.

RAY SUAREZ: So has he learned in the last two years? Have you seen him change in approach, in method? Or has he stuck with something that's been working for him for a while?

DAVID MENDELL: Oh, there's no doubt he's changed since I was running around with him in the campaign van with just me and him and his driver. He was kind of winging it back then. Things were much more organic, and he had all these ideas. And when he stood up before a crowd, they just kind of flowed from him.

But now, of course, I see him when he stands up before a podium, and he pulls out a script, and he reads it. That's just -- you know, those are the parameters of a presidential contest. You have to stick to your message of the day.

So he's matured as that kind of candidate. But it's -- you know, he's a little more shallow in a way, too, because he can't converse with an audience the same way he could previously. He has to stay on his script.

Avoiding risks to succeed

David Mendell
Author
Well, I think that was the most genuine moment I've seen in the campaign. That was the speech that sounded like the Barack Obama I knew when he was running for the U.S. Senate, where I could see his language and what he really felt.

RAY SUAREZ: Shallow or more guarded because of the political near-death experiences with the pastor, with the speculation about his background, with race identity, and whether he was too much or not enough?

LAURA WASHINGTON: He's not going to take any risks that he can't afford to at this point. And he's already been through the crucible, as you said.

The reason why he chose Joe Biden is because that was the most regular, most reliable, most acceptable vice presidential candidate he could have named.

He has a cadre of, like, three or four people who work with him who know him inside and out, and those are the only people he trusts, and those -- people like Valerie Jarrett, for example. And they guard him through that whole -- they keep him away from the risks.

And it's sort of like, for example, the race issue, as you mentioned, the preacher, that was the last time he really had to talk about race, because he had to get that preacher problem out of his hair.

But he's not -- you're not going to see him talk about race. You're not going to see him talk about African-Americans or blacks, because that is too risky of a strategy for him at this point.

DAVID MENDELL: Well, I think that was the most genuine moment I've seen in the campaign. That was the speech that sounded like the Barack Obama I knew when he was running for the U.S. Senate, where I could see his language and what he really felt come out in that race speech.

RAY SUAREZ: He has to succeed the way a lot of the modern generation of black politicians succeed, getting a large share of white votes this time. This is something different, isn't it?

LAURA WASHINGTON: It absolutely is. He's shown he can do it. He did in the primaries. That's the reason that he is standing before us tonight.

But he still has to crack some of those working-class white voters that we've heard so much about in some of the swing states, people who just don't -- those are the people who really don't know him, who really don't get him.

And I don't know that he's come up with a way of doing that yet. I think we'll hear -- we'll see how he does with that message tonight.

But I think that he's just such an unknown to that group of people. People talk about Hillary Clinton voters. A lot of those voters were not Hillary Clinton voters; they were anti-Obama voters. And he hasn't figured out how to get to those people yet.

RAY SUAREZ: Laura Washington and David Mendell, good to talk to you both.

DAVID MENDELL: Thanks for having us.

Obama ran effective timely campaign

Mark Shields
Syndicated Columnist
You know, the idea that you're going to wait four years -- I mean, Joe Biden ran in 1988. I mean, Democrats are different from Republicans. You get one shot on the Democratic side.

JIM LEHRER: Thanks, Ray.

And let's pick up on that, Mark Shields, David Brooks.

Mark, from Springfield to tonight, 19 months, a campaign, how would you characterize his campaign, his campaign for this nomination?

MARK SHIELDS, Syndicated Columnist: Well, first of all, every campaign is inevitably a mirror reflection of the candidate, both in shortcomings and strengths. I mean, remarkably disciplined, a campaign almost free of infighting, no public bickering...

JIM LEHRER: Infighting within the staff?

MARK SHIELDS: Within the staff. I mean, it made it very difficult to cover for journalists, because there was nobody leaking. Most campaigns are like a colander. I mean, you pour it in and leaks come out just in every direction. So in that sense, it was incredible.

At the same time, it was an instinctive campaign, because the cautionary counsel he received was, "Wait. Go back. Run for governor. Establish your credentials." And he understood and those around him understood the central truth: The ball comes around once. You better grab it when it comes.

You know, the idea that you're going to wait four years -- I mean, Joe Biden ran in 1988. I mean, Democrats are different from Republicans. You get one shot on the Democratic side.

John McCain ran twice. Ronald Reagan ran three times. George Bush ran -- his father -- ran three times before they finally got to the presidency, got the nomination. Bob Dole ran three times. With Democrats, it's once and out.

JIM LEHRER: You never hear of these guys again.

MARK SHIELDS: You never hear of them again. And Barack Obama, they seized it.

Obviously, the anti-war was the key. It gave him his uniqueness in the field, gave a chance for him as a compelling messenger to make his case. And make it he did, to audiences upon audiences, and enlisted them with a fervor and a passion that was unmatched in this year.

Pragmatic and hopeful election

David Brooks
New York Times
And in the piece before, if you noticed, his University of Chicago Law School office, he had Harold Washington on the wall, not Jesse Jackson. He is a professional politician.

JIM LEHRER: David, we, the three of us, talked about this campaign throughout, of course, every Friday night. And you commented -- you made comments all the way through, Hillary Clinton was running a good campaign at first, and this, and whatever.

What strikes you now, looking back on the 19 months, of what Obama did or did not do?

DAVID BROOKS, Columnist, New York Times: Well, the discipline that Mark talked about, the niceness. The people around him are genuinely nice people, the policy people, like Samantha Power, who left, or Austan Goolsbee, the political people, like David Axelrod. They're genuinely nice people, which was not always true of the Clinton people, to be honest.

But what strikes me looking back was the adaptation. The beginning of the campaign, it was really about spiritual uplift. It was about you and how we were going to be better and more hopeful.

And then, as the campaign progressed, it became -- because of the Clinton struggle, it became much tougher. It became more pragmatic. It became more bread-and-butter.

And then, when he broke his pledge on the campaign finance, I think it hit another even pragmatic level, much more ruthless.

And the thing that strikes me about Obama looking back, which I didn't appreciate in the beginning, is in Chicago in those days, in the 1980s, there were two black leaders who were really the big leaders, Jesse Jackson and Harold Washington.

And I would remember they would speak back to back. Jackson was the activist; Harold Washington was a professional politician.

And in the piece before, if you noticed, his University of Chicago Law School office, he had Harold Washington on the wall, not Jesse Jackson. He is a professional politician.

I always thought -- he thought of himself as a professional politician. He was going to do whatever it took to win. And so that ruthlessness, which a lot of us like me didn't see at the beginning, it was always there, but that ruthlessness has come out.

He'll do what it takes to win. And that's meant a certain amount of bobbing and weaving.

MARK SHIELDS: One man's ruthlessness is another man's purposefulness. I mean...

DAVID BROOKS: Yes, I didn't mean that pejoratively.

MARK SHIELDS: Yes, I know. I know. And I don't think David did. But the Harold Washington thing is awfully important.

I thought in Elizabeth's piece, I thought what was also fascinating was you realize how much luck plays in this thing, Jim. He challenged Bobby Rush. I saw Bobby Rush today in this city. He's a congressman from the South Side to this moment.

If Barack Obama had won that race, he would be a congressman from the South Side of Chicago, because it would have prevented him from moving statewide, because his political base would have been an overwhelmingly African-American base.

And the likelihood of his seeking and winning a Senate nomination from an overwhelmingly African district would have been remote.

JIM LEHRER: Interesting point. OK.