An Early Setback

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    Cassandra Butts   Harvard Law classmate

    A close friend and former classmate at Harvard Law School, Butts served as deputy White House counsel in 2009. She discusses their long friendship and talks about how Obama's unusual background has informed his approach to politics and policy. This is the edited transcript of an interview conducted by producer Michael Kirk on July 10, 2008 for The Choice 2008.

    ... Did he call you somewhere along the line and say: "You know what I'm thinking about doing? I'm thinking about running against Bobby Rush"?

    Did he consult about the decision? I think that he'd made the choice that he was going to run against Rush. Objectively, it wasn't a bad choice, because at the time, Rush had been weakened by his run against Mayor [Richard] Daley for the mayor of Chicago, and had lost pretty significantly, and had even lost to Mayor Daley in his district.

    Objectively looking at that, you know, you could say that there's a weakness there. And so I think that the assessment wasn't necessarily incorrect.

    But you have to appreciate at that time, I was working for Dick Gephardt [D-Mo.], who was the minority leader in the House of Representatives. And so Bobby Rush was a member of our caucus. And I knew what a challenge it was to mount a race against an incumbent, to mount a primary challenge against an incumbent.

    And I also appreciated that that was exponentially more difficult in a district that was predominantly African American. In African American districts, usually the member who is generally African American stays for quite a while, and to mount a primary challenge is just very difficult.

    So I think that before he got in touch with me, he had made a decision that he was going to run. And I don't think that anyone was in a position to talk him out of that run. And again, objectively, it wasn't a bad choice.

    But he just got his ass handed to him.

    Of course there's an irony that he couldn't win a congressional seat, but he could win the U.S. Senate. There's an irony there, obviously. But it's also just really informative to the broadness of Barack's appeal and his reach, and that the coalition building that we talked about, his experience and Mayor Washington's experience, and his recognition that you had to bring together coalitions. And he was able to do that with the U.S. Senate race, but he wasn't able to do that obviously in the House race. ...

    What did Bobby think of this upstart?

    I think he saw him as an upstart. I think he definitely saw him as someone who was more privileged than his experience had been. As you appreciate, Bobby Rush cut his teeth as a Black Panther in Chicago, and obviously Barack's background and experience was quite different. And so, you know, I think he saw him as someone who was an upstart, who was green and who had a lot of talent, but not necessarily -- he wasn't favorably disposed to Barack, to put it mildly.

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    Obama's Ambition

    Cassandra Butts   Harvard Law classmate

    A close friend and former classmate at Harvard Law School, Butts served as deputy White House counsel in 2009. She discusses their long friendship and talks about how Obama's unusual background has informed his approach to politics and policy. This is the edited transcript of an interview conducted by producer Michael Kirk on July 10, 2008 for The Choice 2008.

    What did he take away from Rush? I mean, you always learn more when you lose than when you win. Did he ever talk about what it was that he learned from that experience?

    I know it was obviously incredibly informative. He didn't talk about it in great detail, about what he learned from the experience and how instructive it was for him in future races. But I think that it certainly allowed him to learn his strengths and weaknesses as a candidate, what he needed to improve on, how he needed to improve his pitch as a candidate.

    Again, he didn't really dwell on the loss as much as, you know, he internalized it and it became an important part of how he has thought about future races. But he didn't talk a lot about it. That's just generally not Barack's style.

    What's up with this guy? Is it, like, naked ambition? What's going on with him? I mean, he's so young. He's so green. And all of a sudden, bam, bam, bam.

    No. You know, he obviously describes himself as being restless and being ambitious. It's not naked ambition at all. It's not that he feels that if he doesn't run, then, you know, the world's going to fall apart. But he really believes that he has something to offer and that he can make a difference, and he can make a difference in the way people live their lives. I think as he continues to believe that, he'll continue to offer himself in public life. And that's where we are today. He's held that belief obviously through the good and the bad.

    It's not ambition to see himself in the limelight, you know? I think if left to his own devices, Barack, as I indicated, Barack would be a writer. He would be in a profession that was more -- well, I was going to say thoughtful [Laughs] -- in a profession that allowed him to be more thoughtful and to be more reflective.

    I think one of the challenges of running for president -- and this is one of the things that I impressed upon him when we were going through the session of, you know, these are the things that you've got to be prepared for -- is that you don't get a lot of time to reflect on what's going on. And that is very much Barack's personality. He wants to reflect and distill what's happened during the course of a day, and you don't get a lot of chance to do that in a presidential campaign.

    But it isn't an ambition that he must see himself in the limelight; he must see himself as the leader. It is that he really does genuinely feel that he has something to offer.

    Just an example, this notion of his ambition: I campaigned in New Hampshire and [former Sen.] Bill Bradley [D-N.J.] endorsed Barack at that point, and came to New Hampshire to do some campaigning for him. ...

    And he said that you see politicians and they're in front of a crowd, and they're soaking up all the energy from the crowd, and they're getting big, and they're swelling up, and that what attracted him to Barack was that when Barack is in front of a crowd, he isn't absorbing the energy that they're giving him and getting larger and becoming puffed up. He reflects that energy back on the people who are in the crowd. He energizes them.

    I thought that that was incredibly insightful. And it does go to this notion of, what's his ambition? And it goes back to him as a community organizer and the kind of leadership style that he has, that he reflects the energy and that ambition back to the people who are out there in the crowd. It isn't him soaking in their energy and being the kind of leader that is the only one on the stage. He has this ability to bring people in the process where they really feel that they're part of the process and that they can make a difference. And that's, I think, his skill as a politician.

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    Gerald Kellman   Hired Obama as a community organizer

    He is the community activist who gave Obama his first job in Chicago, organizing black neighborhoods to push for local change. This is the edited transcript of an interview conducted by producer Jim Gilmore on July 24, 2008 for The Choice 2008

    You explained why he ran for Congress, because it was one of the few opportunities for a black politician. What's the lessons learned when he loses? I mean, he's a bit despondent for a while. But when you look at it, when you talk to him during that period of time, what does he gain from that?

    There's a couple of things. 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, and 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.

    And at some point, he ends up looking at a office where his gifts for working with different people together and bringing diversity together will be helpful to him, rather than a minus, as it was in the congressional campaign, where his broad sense of narrative and of getting to the roots of issues rather than the more superficial ward heeler, if you will, kind of issues are much more important.

    So the only option left to him is the option that he has gifts for, which is 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.

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