In 2008, when Obama first took office, The Maroon spoke with some of the people who knew Barack Obama as a professor or as a colleague while he was teaching in the law school. We reached out to a few of them to reflect on the eight years of the Obama presidency and look back on his time both as a professor and as President of the United States.

GEOFFREY STONE – Edward H. Levi Distinguished Service Professor at the University of Chicago

Geoffrey Stone was Dean of the University of Chicago Law School when Barack Obama became a lecturer. He is a member of the Board of Directors of the American Constitution Society and the Board of Advisors of the American Civil Liberties Union, and has frequently worked with Obama on national security issues. In 2008, we asked Stone how important Obama’s academic experience had been:
 

Geoffrey Stone in 2008: There is a sort of caricature of the kind of absent-minded professor, where someone could be so academic and abstract, but that’s not the experience Barack had, since he was not a full-time academic. But in meaningful ways his experience helped to reinforce and hone some skills and attributes that we see in him today and are in part a product of the experience he had with the University. Genuine intellectual curiosity, openness to listening to all sides to an issue… The culture here is very strong and fairly definable, and my sense is Barack brought those characteristics to bear in his teaching.

Chicago Maroon: We’re going to start off by asking literally the same question we asked last time: How does it feel to have been one of the people to hire the man that has become president?

GS: Well, it was a great honor to have gotten to know Obama and to have been one of those people who identified him when he was still just a law student as someone who had the kind of character and personal ability to eventually become president of the United States. I think that all of us here are very proud of the fact that he was a colleague for as long as he was.

CM: In the same article, you mentioned his “genuine intellectual curiosity, openness to listening to all sides of an issue… The culture here is very strong and fairly definable, and my sense is Barack brought those characteristics to bear in his teaching.” Do you still see these characteristics in his presidency?

GS: When you talk to people who have worked in the cabinet or otherwise, one of the things they constantly say is that he always asked questions, he was always curious, he always wanted to more deeply understand the complexities of issues. My own experience dealing with him as president, on national security issues was exactly that. So, I think that the kind of intellectual rigor that was reinforced in him in the time he spent here has stayed with him as president, and is very much a part of his intellectual leadership style.

CM: Following up on that, I’ve been reading some of the stuff that you’ve put out, especially these last two years, regarding Edward Snowden, regarding Merrick Garland, and you seem to identify a very strong partisanship in the House and the Senate, particularly on the part of the Republicans…how does this tie into what you identify as a general openness on Obama’s part?

GS: Well, I think Obama faced a determined, hostile opposition from the day he was elected that is extremely unusual in American politics, that members of the opposition party made it very clear from day one that for whatever reasons of their own, that they were not going to see compromise, they were not going to see common ground, they were going to do everything they could do to obstruct whatever goals Obama was bringing to the presidency.

The irony there to me is that Obama is by nature someone who seeks common ground, he’s not an ideologue, he’s not close-minded, he’s an incredibly reasonable person. It should’ve been very easy for Democrats and Republicans under an Obama presidency to have found common ground to solve some of the nation’s problems, but Republicans in the House and Senate throughout his tenure have simply refused to do that, and I personally find that appalling.

I think that’s a betrayal of their responsibilities, and it’s captured really perfectly by the response to the Merrick Garland nomination, where the President nominated someone who was clearly designed to be acceptable to the Republicans…older than any nominee in 40 years, which meant his tenure on the court would presumably be shorter, and more moderate than any nominee in recent memory. And that was clearly done by Obama as an effort to serve an easy path to a confirmation, and the Republicans said no, we’re not going to have anything to do with it, and they had no principled or legitimate path to doing that.

That typified, I think, the problems that the President faced during his tenure. I think it’s a real breakdown of the understandings of democracy, which is designed to create a culture in which there is opposition, but in which there’s also an effort to accomplish things.

JOHN BOYER – Dean of the College

John Boyer has been the Dean of the College since 1992, and has been a member of the faculty since 1975. He published *The University of Chicago: A History* with the University of Chicago Press in 2015.

We asked Boyer in 2008 how important he found Obama’s academic experience, particularly compared to Woodrow Wilson, and he characterized the two presidents as sharing some ideological similarities:

John Boyer in 2008: It seems to me that one could say that Obama shares two broad areas of talent and capacity with Wilson. Wilson is most famous for his internationalism, sometimes called Wilsonianism—supporting democracy abroad, rule of international law. And so, Wilson was a very much of an idealistic president. I think Obama comes from the same cloth. Not the same kind of idealism, but he thinks in terms of large ideals.

The second, which Wilson didn’t have enough of, is the pragmatism of a community organizer. I think that’s one of the most remarkable things about the campaign—it’s going to be the subject of doctoral theses—thousands and thousands of people playing the role of community organizers. It’s a tough pragmatism: Set aside ideology and broker compromise. It’s a side of him I’m not sure Wilson had, or had enough of.

CM: So, to start off, you mentioned in our original article that the Obama administration was basically making “thousands of thousands of people into community organizers.” Have you seen that sort of ideal followed-up in his presidency?

JB: That’s the world he came from. The life of the Springfield and then to the U.S. Senate and then to the presidency. I don’t know whether the level of community organization has increased in the United States…it probably has, whether there’s a cause and effect between his being elected or not….

He inspired a whole generation of younger people, or young people, to take an interest in civic affairs. You can take an interest in civic affairs in many ways apart from paying your taxes and voting, or by joining a local school board or whatever, but certainly community organizing is one prominent way of becoming involved in civic affairs.

I think this really in a sense gets us to the kind of larger impact of his presidency as a whole…. You probably have to go back to Kennedy, because of the personal charisma, because of the biography, because of the autobiography, because of the kind of person he was and where he came from, there was this kind of inspiration factor. A lot of it did translate into working in not just community organizing but local government. A lot of our students now who want to go on to do government work are interested in local politics, because they feel like they can accomplish something there.

CM: Not just Kennedy but also…there’s been this connection to Woodrow Wilson that a lot of people have brought up because of this sort of connection to an academic institution. How do you, as a historian, see any sort of comparison there?

JB: I mean, Wilson was the president of Princeton and a prominent faculty member there, and then became governor of New Jersey, so he had a lot more experience in what we’d call academic administration than Barack Obama did. I mean Barack Obama was a part-time lecturer over at the Law School.

I think the comparison with Wilson, or the more accurate or more plausible comparison would be that Wilson was this kind of an idealist in terms of international politics, and Obama seems to me was kind of an idealist in terms of domestic politics. Both were internationalists, but Wilson’s internationalism came at a very different time with WWI and the ravages of the war, the League of Nations and so forth. Obama’s internationalism has been more crisis containment and one could argue, I suppose, that it’s been more on the economic realm, expanding relations with China and the Pacific economies. So I think there’s some parallel there but I actually…the comparison with Kennedy is the stronger one. That’s why I think it’s interesting to follow up, cause some of these things don’t end up panning out.

And also, to be candid about this, it’s also youth. We forget that—I think that part of the magic that Obama had in ’08 was that he looked, seemed, and was young to young people or younger people, and that’s the same—my generation was inspired by Kennedy, I mean, he was older than we were, but he seemed like us.

CM: Your bike tour has often stopped nearby the Obama house, can you give me sort of a taste of what goes on there?

JB: Well, it’s the last stop, and we’ve never been able to get very close because of the secret service. After the 20th, I don’t know whether…what the rules of engagement are for former presidents, whether they’ll let us go closer or not.

We put that stop on the tour after he had been elected…. It was a way of saying something not only about him, but also something about Kenwood. This is a neighborhood that was once the kind of preserve of the wealthy elites of the city…. It was sort of like the Gold Coast or the Winnetka or the Kenilworth of the South Side. It fell on really hard times in the ’50s and ’60s, there was a lot of depopulation there and it came back in the ’80s and ’90s. The fact that Barack Obama and his wife bought a house there, invested in it…I mean this is part of a movement, you could argue, of upper-middle class, middle-class people back into Woodlawn, Kenwood. It’s interesting because today Kenwood is a flourishing neighborhood, almost all the houses are occupied by residential owners and so forth, with the exception of course of Mr. Obama, who doesn’t live there except for when he visits the city. 

RICHARD EPSTEIN – James Parker Hall Distinguished Service Professor Emeritus of Law and Senior Lecturer at the University of Chicago Law School

Richard Epstein has been teaching at the University of Chicago since 1972, and knew Obama during this time at the Law School. He is the Peter and Kirsten Bedford Senior Fellow at the Hoover Institution, dedicated to “advancing ideas that promote economic opportunity and prosperity, while securing and safeguarding peace for America and all mankind.”

In 2008, we asked Epstein what Obama might share with Wilson, another president with an academic background. Epstein recounted some of the mistakes of the Wilson presidency:

Richard Epstein in 2008: I hope Obama doesn’t make the same mistakes. He thinks you can impose taxes and achieve redistribution of wealth, and doesn’t look at alternative strategies people might employ. There’s a great deal of similarity.

Obama comes from academic experience on one issue, which is the race question, on which he’s very astute. But that’s 10th on the list of issues he needs to deal with. With all of those issues, the more you know about them, the less confident you are.

CM: In our original article, you said that Wilson “resegregated public service”, and was “able to drive corporations out of New Jersey by imposing a tremendous tax on them.” You said then that you hope that Obama doesn’t make the same mistakes, and I was just wondering whether you think he has.

RE: Epstein objected to Obama’s actions in essentially every policy area, including executive power, race and policing, foreign policy, trade, and health care policy.

So it is very difficult to come away with any particular area, domestic or foreign, in which you think the United States is better off today than it was when he came into office. When one thinks of this sort of optimism, you know, that this is the time in which the seas will cease to rise, well they continue to rise at the same rate as they have always done, and, you that we will have peace around the world, that was just completely misplaced. The man is just not a deep thinker. I mean, I know he kind of puts it on, but what always struck me about Obama, as I mentioned before, and we all knew him, and he was a good listener, and then when it was all done, you had your say, and you stop and then, well, what did he think? And you could just never figure that out.

Just…just a very hard man to read. And other people have said the same thing, and people used to say, well that’s just because he wants to preserve his options, well, I’ve come to believe that’s just because he didn’t know what he wanted to say about these kinds of issues.

So his legacy will be one which I think will not be viewed with favor. If you go back and listen to that 2008 debate, you’re going to hear Cass Sunstein eventually, who worked for the man, extolling his many virtues, you can hear me essentially demurring on all of these points. I just went back and listened to it and I think in fact I was too kind to him on too many issues, that he is in fact actually worse than I thought.

None of this is meant to be an endorsement of Donald Trump, about whom I have many reservations, but it is meant to be a condemnation of a president who had to be able to speak out more forcefully than he did. One of the things that Cass said in that debate was, well, he went to black churches and told them what they had to do, made it appear as though he was willing to speak truth to power, now it turns out he was silent when he had to speak the most, and we are weeping alone regardless.

It’s going to take a long time before we can heal the cooperative situation in the United States, in terms of our public policy. It’s also very clear that the Democratic Party has moved very far to the left. Ironically, I think that Obama is now to the right of people like Hillary Clinton, Bernie Sanders, Elizabeth Warren. I wish him well when it comes to trying to control those excesses, but I do think much of this stuff took place on his particular watch because he could not articulate a clear and powerful vision of what it was that the United States should do in matters of civic trust and civil order. Those are matters in which I think he fell down very badly.

And so you look at health, you look at race relations, you look at the economy, you look at trade, you look at the environment, you look at energy, you look at foreign affairs, I don't see anything that comes out as a strong positive for him. I think my views are to some extent shaped by my libertarian preferences, which are pretty strong and well developed, but I think even neutral observers whose politics are somewhat more conventional that my own would say that he did not succeed in making sure the middle held. There’s a famous line from William Butler Yeats, he said “the center will not hold”, and that’s exactly what seems to be happening in American politics.

DOUGLAS BAIRD – Dean of the Law School from 1994 to 1999

Douglas A. Baird served as Dean of the Law School when Obama was hired as a lecturer. He is an expert in corporate reorganizations and contracts. In 2008, we asked Baird how he felt being the former boss of the President of the United States:

Douglas Baird in 2008: It’s absolutely not sunk in yet. It’s really quite amazing. This is someone who 10 years ago, if you wanted to meet him, all you had to do was go to the Field House and he was playing a basketball game. All you had to do was go to the gym. Right now, I’m one of his 100,000 closest friends. He’s gone a long way.… What we can do is have some small vicarious thrill thinking we might have pushed him a bit. He could have started at any law school in the country and done fine. Those qualities that were inherent were what drew him to us.

CM: Can you identify Obama’s history with the University of Chicago on his four years as president?

DB: One of the things that’s changed over the last eight years is that now he is thought of by his friends and his critics as having started life as a constitutional law professor. If you look at the way sometimes he’s critiqued, they say, well he’s too abstract, he’s too remote, and he’s not political enough, and he’s not like Lyndon Johnson, he doesn’t get engaged in the messy business of politics, he’s too cerebral, he’s too much the law professor.

Now, other people, you know, celebrate the fact that he is a thoughtful, deeply intellectual man who understands core values and core issues. At the time he was running for office, you know, the republican attack on him was not that he was a constitutional law professor, but that he was a community organizer, which is just not…you know, it wasn’t true at the time, it didn’t actually capture him.

CM: What do you think do you think of Obama’s legacy, either on the Law School or more generally?

DB: Oh, I think history will treat Obama very well. I think a lot of people, especially younger people especially don’t remember this country was in, you know, this…awful shape at the time he became president. The economy was collapsing, the automobile industry was collapsing, the banks were collapsing, unemployment was sky high, and we had hundreds of thousands of people fighting wars we shouldn’t be fighting in Afghanistan and Iraq, and you can always critique someone and it’s very easy to do, but the reality is the really bad things our country was facing when he took office, he fixed, and I think history will give him a lot of credit for that.

I’m also very proud of the University’s role in informing him. I think that he has, again, whatever you think about him, I don’t know your politics, whatever your politics are, I think as a head of state, you know, bringing dignity into the office, I think he’s done his work impeccably. I think he’s really brought stature and class to the office and people are going to remember that, so, again, I think that’s something the University is going to take a lot of pride in.