Obama's Ambition

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    Tom Topolinski   High school friend

    A member of the "Choom Gang," Topolinski was a close friend of Obama from his days at Punahou high school. This is the edited transcript of an interview conducted by producer Jim Gilmore on June 30, 2012.

    The idea of leaving and going to Occidental and all, what was motivating him at that point?

    First of all, it is very easy to become complacent when you live in paradise. When the living is good and free and easy, it's easy to just kind of exist. But many of us did not feel just that. We wanted more out of life, and I definitely think that this was already a template for Barry, for him to follow. I don't think he would have been happy living in Hawaii his entire life. He was one of those that needed more. The same goes for me; I’m living here in Washington now because living in Hawaii was great, but it stopped becoming a growth experience. And it was all about growth.

    And I think Barry grew into his own, and the path that he did follow was always there. It was easily forgotten about in high school, but once we were released into the world at 18 years of age, I think a lot of us had flipped the page and said, OK, now we need to get on with life. And I think Barry did that very, very diligently. And I'm not surprised that he is where he is today. …

    When did you notice, oh, my God, my good buddy Barry is moving ahead in the world? Do you remember hearing things over the years that sort of impressed you and surprised you? ...

    You know, I had lost touch with Barry, and then one day about five years ago I had heard that he had become active in politics, had become a senator, and did well in the college part of that, getting his law degree. He had that intelligence. And so I was surprised, but then at the end I was like, not surprised at all.

    And then I heard something about his name and "presidential" being lumped in the same sentence, and I caught myself, and I was a little amazed, surprised, confused. And then as I read more and I got on the Internet and I did a little bit more Googling, and you're kidding, Barry wants to be president? How can this be? He was one of us! How does this happen? (Laughs.)

    To this day, I don't think it's hit me. Every time that I walk by the TV and see Barry on there, I don't know that I've connected with that yet. It just seems so surreal. And I mean that in a good way.

    In some aspects, one of his favorite words in high school was "veto," which is why you'll see in one of the pictures that some of us going like this or like this, which could be saying peace, but in our Choom Gang, it was "veto." We loved to get on someone who had an idea: "Hey, let's cut class and go to the beach." "Veto, I've got a test tomorrow." Barry was using that word freely at the time. …

    So did I see this coming? Not really. But now that I've seen him, I'm starting to realize he really is our president, and this is not a dream. But it's still surreal, very surreal. …

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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 mentioned that in connecting it to power, power is what this is all about in a lot of ways. Explain that.

    Well, I gave Barack two books to read. And the first book was by Robert Caro, who's written this wonderful multivolume biography of Lyndon Johnson. But I gave him The Power Broker about [New York City architect] Robert Moses, and how power is often exercised behind the scenes and the public doesn't have access to it, and it's exercised for all kinds of reasons other than the stated reasons, so sort of the dark side of power which he learned personally in Chicago, too.

    Other hand, I gave him Parting the Waters, Taylor Branch's first volume, biography of King and the civil rights movement, so maybe the upside of power at the same time and where they fit together.

    But yes, power. We were working with people who had no power, and what we were trying to do was at least level the playing field in terms of power. And I think that, as we move into seeing what Barack, what positions he takes on public policy, a lot of this is about leveling the playing field, not to seize power from one group and give it to another, but to give people an equal shot at the economic resources, the social resources. ...

    And part of the lesson I suppose in becoming a good community organizer is to figure out how one attains power. What are some of the lessons that are taught that he had to learn about power and how one attains it?

    ...Certainly what he learned is that the stated reasons for people doing things were not necessarily the actual reasons. And he came to Chicago, and the last of the great political machines, the Democratic organization, the regular Democratic Party of Cook County, was still very much intact when Barack got here. Harold Washington had been elected mayor, but the city council was controlled by the machine.

    And Mike Royko, the columnist of those years, said the city motto of Chicago was, "Where's mine?" And Barack learned that very quickly. It didn't matter who was the state representative or the state senator or the alderman -- that's the city councilman of Chicago. It mattered who the Democratic ward committee man was. He called the shots or she called the shots. Whoever is the official representative of the Democratic Party gave the marching orders to the public officials.

    And then when you met with people who were the ward committeemen, you needed to know something about them. You needed to know their side business. Were they an attorney? Did they sell insurance? Were they a real estate developer? Because often what they did was dictated by that kind of motivation. Who were their relatives, and who did they work for?

    It quickly dissuaded him of any illusions he had about self-interest and how it's used in the political process. Barack came to Chicago very idealistic. Part of our job was to make him more practical. He left idealistic, but he left with a strong streak of practicality; that if you're not practical, you don't do anybody any favors, and you and the people you're working for get their brains beat out. ...

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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

    When do you see the first spark of interest in politics?

    In electoral politics?

    Yeah.

    I don't really know he's going to go there until he tells me he's leaving organizing, he's going to go to law school, and he's going to do that.

    But when he tells me that, he tells me why. And it makes sense, that what he wanted to see was large-scale change. And community organizing changes small issues in people's lives, and we transform people's lives in terms of teaching them skills and giving them hope they didn't have before. But it structurally was not going to change racial discrimination. It was not going to change poverty in the United States. There simply would not be enough power there.

    That would only come through electoral politics. And that's what he said to me when he said he was going to leave. That was one of the reasons for leaving organizing. But I did not see that he'd go in that direction until he told me.

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    Related topics:
    Harvard Law School

    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

    Why the law degree? Why did he think he needed the law degree from Harvard?

    Barack was part of a world that most people running for president never impart, a very grassroots world, the world of the streets, so he understood that part of the world. But you also as president have to deal with the wealthy and powerful. I mean, most people only have that experience. I mean, I think probably George Bush was given the card, the Skull and Bones at Yale, probably when he was baptized.

    Barack didn't have that experience. He had the grassroots experience. He had the experience of being an outsider. He didn't have the experience of connectedness to the levels of public policy and academia and government that other people might have had. And to do that, he needed to connect with one of the major universities.

    And law school made a lot of sense to him. If he had a hero as a president, it would have been Abraham Lincoln from Illinois. Lincoln was a lawyer, and certainly many of the great figures in the Democratic Party, Roosevelt, Kennedy, you know, they had been attorneys. It was the logical choice for him to make. ...

    You said that his dad's legacy comes into play big time on his decision to go to Harvard. What did you mean by that?

    Well, the second reason that he gave me when he told me he was leaving -- and understand, we're at Harvard at the time. We're attending a conference on the black church, which is sponsored by the Harvard Divinity School, and we're walking around the campus. He was just getting to know his father's biography in a more detailed way. I mean, his mom really wasn't in touch with his father; there was nobody giving that information. But his half-brother and half-sibs were beginning to come over to the States and to Europe to go to -- and then to the States to visit, to go to graduate school from Kenya, and so he's getting the story.

    And the story as he understood it was that his dad had been overly idealistic and not practical. They had fallen on the outside of the government in Kenya. And not only had he been ineffective at dealing with his own ideals, but he ended up impractical and destitute financially.

    And although Barack didn't have much interest in wealth, he had a strong interest in having a secure income to marry and raise a family. He did not want to follow in his father's footsteps. He wanted to be more practical in his choices and more practical in terms of how he might bring change to the country. And so his perception of who his father was figured in that.

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    Laurence Tribe   Obama's Harvard Law professor

    (Text only) A longtime professor of constitutional law at Harvard, Tribe recounts the day "a tall, skinny kid" appeared in his office and said, "I'm Barack Obama. I'd like to talk to you about the Constitution." This is the edited transcript of an interview conducted on June 12, 2012.

    Read the full interview »

    He obviously loves the law, thinks about it, talks about it, teaches it even at the University of Chicago as a lecturer at least, but being on the bench didn't seem to be an avenue for him either. Or did it?

    It's not inconceivable. I mean, there have been presidents who have then been appointed to the bench.

    He's very judicious. He loves legal analysis. He can't avoid thinking about the legal intricacies of a problem. He's obviously been confronted with more difficult legal challenges, not only in the context of the drones and the sort of indefinite detention and military commissions, but also the question of whether the president can unilaterally raise the debt ceiling. All of these things have fascinated him, and he likes thinking through him.

    He believes in the rule of law, takes it seriously, doesn't think it's simply politics by another name. So I wouldn't rule out the possibility that he could be chief justice of the United States someday.

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    Laurence Tribe   Obama's Harvard Law professor

    (Text only) A longtime professor of constitutional law at Harvard, Tribe recounts the day "a tall, skinny kid" appeared in his office and said, "I'm Barack Obama. I'd like to talk to you about the Constitution." This is the edited transcript of an interview conducted on June 12, 2012.

    Read the full interview »

    The fascinating thing about him is it's obviously a potential ticket to ride in some way. You're president of the Law Review, you're a Supreme Court justice's clerk; I suppose you could get a great job in Wall Street or in New York if you want.

    Yeah, he had all those options. Not every president of the Harvard Law Review has all of those options. Some of them are very smart but not nearly as charismatic. Some of them are quite charismatic but not as deep. He had it all. And it was clear both because his grades were terrific, because he had worked and impressed, worked for and impressed a number of professors as being really quite brilliant, he had all of those options.

    I think Abner Mikva had made it clear. At that time Ab was a judge on the D.C. Circuit. He had made it clear that Barack Obama could work as his law clerk, and then had pretty much a clear entry to be the law clerk for the great justice William J. Brennan Jr. And I think he struggled for a while with whether he should pursue that path, which could have given him a few years after that of accumulating some real money on Wall Street before going back into community organizing and politics, or whether he should sort of skip all of those things.

    And he talked to a number of his teachers and mentors at Harvard. I was one of them. I think he said, "Do you think I'm making a mistake in not taking up the law clerk/Wall Street option?" And I had no hesitation in saying: "No mistake at all. I mean, unless it's something that you yearn to do, I don't think you need it. I think you have a passion, you have a commitment, and you know what you need to know. People learn a lot by being law clerks to great judges and justices, but you know much more than most of them do after they're done with that experience. And I think you should go ahead."

    I know some of my colleagues were hesitant. They thought he was moving too fast. They thought he ought to take those opportunities, but I didn't.

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    Related topics:
    Harvard Law School

    Laurence Tribe   Obama's Harvard Law professor

    (Text only) A longtime professor of constitutional law at Harvard, Tribe recounts the day "a tall, skinny kid" appeared in his office and said, "I'm Barack Obama. I'd like to talk to you about the Constitution." This is the edited transcript of an interview conducted on June 12, 2012.

    Read the full interview »

    Was there a goal? Could you sense from him that it was more than just academic? Was he formulating something? Was he getting a plan together or a worldview together? Did you have a sense of a practical ambition at the end of this?

    Oh, yeah. I mean, it was not an ambition that at least from my perspective was focused on a specific office or a specific path to power, but it was an ambition to make a difference.

    I meet all kinds of law students, very talented ones usually. Some of them have ambitions to do well in the world, to earn a lot of money, to exert some influence. They often try to hide those ambitions in more palatable terms in terms of doing good.

    This kid was not hiding anything. He clearly was at Harvard Law School to get a better sense of how things worked so that he could fold those ideas, that information into kind of an ongoing project of improving the human condition. ...

    The better he did at Harvard Law School and the more he impressed people, the more obvious it became that he could have had anything. But it was clear that he wanted to make a difference to people, to communities. How he would best make that difference, I don't know if it was clear to him. It wasn't clear to me. But it was clear that he was there with kind of a burning sense of obligation and ambition. And that made him quite distinctive. ...

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    Ken Mack   Obama's law school classmate

    (Text only) Harvard Law classmate Ken Mack recalls Obama's election to the Law Review, the Derrick Bell controversy, and the future president's love of basketball. This is the edited transcript of an interview conducted on June 13, 2012.

    Read the full interview »

    We talked to Laurence Tribe yesterday, and he tells the story of this young skinny guy in Levi's and a bomber jacket showing up at his door, and they spend a few hours, literally hours that first time walking through the constitutional law stuff. ... Is that a fairly typical interaction that he had with Tribe, or was it your sense that there was a sort of special thing going on there?

    I think with Barack and Tribe there was something special going on. I mean, first, Barack was a first-year student. 1Ls, as far as I knew, didn't work for Larry Tribe. He wouldn't hire you. And at some point in our first year, we heard that Barack and his friend Robert Fisher were working for Larry. And people were like: "Wow, that's very interesting. I didn't know that Larry hired 1Ls. He must see something really interesting in this guy." So I think the interaction between Barack and Larry was something special from the beginning. I think Larry saw something that really impressed him.

    What can you imagine it was?

    Barack was very well read in the world. He was intellectually well read, but I think well read in the sense of having a lot of different experiences.

    So when you talked about, I don't know, free speech or affirmative action or the things that we argued about in law school, he is somebody who could think about it on the more philosophical level, he could think about it on the legal level, and he could tell you some stories about how it worked for him out in the real world. And there weren't a lot of people who could put all those three things together. So you always got something out of the conversation with him on just about any topic.

    And who was Larry Tribe? For people who watch this film and don't know the importance or whatever of Larry Tribe saying, "OK, you can work for me," what was the meaning of that?

    Larry Tribe, when we were in law school, was, of course, the most important constitutional law professor in the country, probably the most important constitutional legal theorist of his generation. He was a singularly impressive person on campus.

    So, for instance, after law school, many people go clerk for a prestigious judge as a way of getting a little experience or getting a little bit of prestige or a little bit of both. There was always something called the Tribe clerkship, meaning after law school you could go work for Larry for a year, and that was regarded as just like clerking for a big-name judge. He was that prestigious.

    So for Barack Obama to get a gig with him early and to take long walks along the Charles with him is something special.

    Yeah, it was definitely something special. I mean, people understood that this was different, that this didn't happen to first-year students, and that Barack was clearly somebody who was singularly impressive, impressive enough to impress one of the greatest legal minds of his generation.

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    An Early Setback

    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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    Valerie Jarrett   White House senior adviser

    A close friend of Barack and Michelle Obama from their early years together in Chicago, Jarrett is now a senior adviser to the president. This is the edited transcript of an interview conducted by producer Jim Gilmore on Aug. 20, 2012.

    You become a real emissary to the president back then to power, Chicago power. And you were there for all the different steps that he takes in his political life. Why? What did you see in him?

    Oh, my goodness. I saw this amazingly talented young man who could be doing anything and who wanted to give back, and who was so interested in figuring out what was the right path to take where he could give back to the greatest degree.

    And let's face it: He could be a senior partner at a law firm anywhere in the country, but he chose this political life, and it was never for the short-term political goal of just simply getting elected; it was really more about what he could do once he was in office. So each step along the way I've watched him take on issues that he cared passionately about that are intended to improve society. And it's been an amazing journey, and I feel so privileged to have been able to share it with both of them.

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    Valerie Jarrett   White House senior adviser

    A close friend of Barack and Michelle Obama from their early years together in Chicago, Jarrett is now a senior adviser to the president. This is the edited transcript of an interview conducted by producer Jim Gilmore on Aug. 20, 2012.

    For that Senate race, you and Michelle got together and had a breakfast with other people, and the idea was to convince him not to run.

    Yes, we were going to gang up on him, and we brought together some folks who we thought would help us in ganging up on him and convincing him not to. And in the course of a couple hour breakfast we went from being strongly against it to me agreeing to being the chair of his finance committee.

    So he was able to move both of us a great deal in a couple of hours, and a big piece of it is because he had thought it through. He had figured out who he needed to help support him, what had he learned from the congressional race against Bobby Rush that he would improve upon in this race, and just an absolute willingness to put it all on the line. And if he lost, well, then that would be OK, too.

    And was one of the things that he had figured out was that he had a new coalition that would back him that perhaps he could be more successful with?

    Well, he did have the endorsement of some very key people in Illinois who were willing to go out early and support him, and that was very different than the congressional race against Bobby Rush, where he didn't have that kind of core support.

    He thought he could bring together a diverse coalition, and that that would be important to win in a state like Illinois.

    And he was willing to do the work. He was willing to travel all over the state and pound on every single door and not take anything for granted. He was all in, and when you go all in like that and you're willing to do it, it's hard for your spouse and for your friends to say, well, they're not all in with you.

    One last thing on this neck of the woods is that he seemed to have -- so the Senate race, the coalition behind it was white, was black, was rich, was poor, was Jewish, was Christian.

    City, suburban, downstate. He spent a lot of time, when he was a state senator I should mention, really going downstate. And when you're from Chicago and you go downstate, it's big news. You'd see banner headlines: "Chicago state senator comes to X small city in Illinois."

    So he had done that while he was a state senator, so he was more of a known quantity when he ran for the U.S. Senate. And I think his willingness to roll up his sleeves early on and spend that time downstate led to his benefit during the campaign.

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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

    What is your take on him? Every two years basically, he was jumping to the next large step on the ladder toward amazing power. Where does he get that from? ...

    I think we read that back into the timeline, rather than it being the reality. When Barack returned to Chicago, it was to eventually run for the United States Congress. I mean, that was clearly the position that he wanted and that he aspired to. And if part of the road to that was working in the state Senate, and that was part of it -- the point he's running for Congress, that's what he was pointing toward, probably once from the time he decided to enter politics, which begins probably with Harvard Law School.

    The jump to the Senate wasn't something he orchestrated. I mean, it was thrust upon him, because there was nothing else left. Politically, his back was to the wall, and if he was going to go anywhere, it would have to be to the U.S. Senate as a major public figure.

    But once he begins to go to the Senate, something else begins to happen for Barack, which is that he begins to have a team of people to collaborate with. I mean, Barack is brilliant at pulling together a team of people and getting them to work together, and to work with him. ...

    And then he gets invited to give the speech at the Democratic Convention. And suddenly I walk into a supermarket, and half of the magazines -- and it doesn't matter what they're dealing with; I mean, maybe for all I know, he was on Field & Stream -- have Barack's picture on it. He becomes a media phenomenon. ...

    So when he takes on this next role that he's always taking on, and the presidential role, does he see it as opportunity or obligation? How does he view it?

    Well, I can just say what I know of Barack, and this is, the largest influence on Barack is his mother. And his mother imbued him with a strong sense of achievement, that he should be the best at whatever he does.

    But she also imbued him with a strong sense of service. This is a woman who, when I met Barack, was in Bangladesh developing microeconomic lending programs so women could have spinning wheels in Bangladesh. I mean, a strong sense of service.

    Nobody runs for president of the United States unless they're ambitious. Anybody who thinks otherwise is silly. And Barack does want to be the best. He wants to achieve personally. But he's also got this strong, strong sense of service to others. And so they coexist. ...

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