In the spring of 2000, not long after Barack Obama was trounced in the Democratic primary for a South Side Chicago congressional seat, Daniel Fischel staged an intervention. Meeting with Obama in the main lounge at the University of Chicago Law School, where Fischel was then dean and Obama was a part-time senior lecturer, Fischel offered Obama some unsolicited advice. "I told him that it was obvious his political career was going nowhere," Fischel recalls, "and that he really ought to think about doing something else."

The particular "something else" Fischel had in mind was a full-time tenured professorship; to sweeten the offer, Fischel said the law school would even hire Obama's wife, Michelle, to run its legal clinic. Although the move would require Obama to give up his state Senate seat, Fischel tried to convince his junior colleague that Chicago professor might be a more natural role than Chicago politician for a cerebral guy like him. "I mentioned people who'd been faculty members like [Antonin] Scalia and [Richard] Posner and [Frank] Easterbrook and many others who had gone on to very distinguished careers outside of academia or in combination with academia," Fischel says. "I told him he could be a faculty member as well as a public intellectual."

Obama declined Fischel's overture, saying that he wanted to give elected politics another shot. And today, of course, it's hard to find any fault with the wisdom of that decision. Still, the episode is interesting not only as a counterfactual (how much does Hillary Clinton wish Obama had spent last December grading Con Law exams instead of stumping in Iowa?) but as a window onto Obama's relationship with those who don't share his ideology. The University of Chicago Law School, after all, is a famously conservative institution--the birthplace of the law-and-economics movement and the incubator of numerous conservative intellectuals; Fischel himself literally wrote (with Easterbrook) one of the fundamental books on law and economics, in addition to another book arguing that the government's prosecution of Michael Milken was unjust. Yet, eight years ago, there was something about Obama that made Fischel and other Chicago conservative legal scholars want Obama to be their colleague--and today, at least for some of them, maybe even their president.

Obama first came to the University of Chicago Law School's attention via one of its more celebrated conservative faculty members, Michael McConnell, who's now a federal judge on the Tenth Circuit Court of Appeals and reportedly was on George W. Bush's short list of potential Supreme Court nominees. Back in 1990, when McConnell was still teaching at Chicago, he wrote an article about church- state relations for the Harvard Law Review that Obama, who was then the Law Review's president, edited. As McConnell recently recalled the experience to Politico: "A frequent problem with student editors is that they try to turn an article into something they want it to be. It was striking that Obama didn't do that. He tried to make it better from my point of view." McConnell was so impressed with Obama that he recommended him to the head of Chicago's appointments committee at the time, Douglas Baird, a bankruptcy expert and a law-and-economics devotee. "Michael's a very smart guy who's basically a very good judge of horse flesh--he wouldn't typically recommend people," says Baird.

Baird approached Obama about a teaching job at Chicago during his third and final year as a student at Harvard. "You look at his background--Harvard Law Review president, magna cum laude, and he's African American," Baird says. "This is a no-brainer hiring decision at the entry level of any law school in the country." But Obama wasn't interested. Obama did, however, mention that he was writing a book on voting rights, so Baird arranged for him to become a Law and Government Fellow at the school--a position that provided Obama with an office and a modest stipend he could use in the course of his writing. When Obama came to Baird in the middle of his fellowship to report that his book on voting rights had morphed into the memoir that would become Dreams From My Father, Baird told him not to worry. "It was a good deal for us," Baird explains, "because he was a good teaching prospect and we wanted him around." Indeed, after the publication of Dreams, Baird, who was then dean of the law school, took another shot at hiring Obama as a professor. Obama, who was in the midst of successfully running for the state Senate, once again declined. But he did accept the law school's offer to become a senior lecturer--then a title held only by Posner and Easterbrook--and teach a reduced course load of three classes per year.

For the next eight years, Obama taught upper-level constitutional law courses on equal protection and voting rights. He was a huge hit with his students. According to the Chicago Sun-Times, which reviewed students' evaluations of Obama's courses, he was almost always rated one of their favorite instructors during his time at Chicago. Given the subject matter of Obama's courses, one might assume that students in the classes--which were electives--would have been disproportionately liberal. But Chicago's reputation for producing law professors tended to mitigate against that. "Anybody who's thinking they want to go into academia, conservative or liberal, kind of knows they have to take equal protection," says Kenworthey Bilz, who took equal protection from Obama in 1997 and is now a professor at Northwestern Law School. "I can very confidently say he didn't strike me as liberal or conservative."

Because of his political duties in Springfield, Obama scheduled most of his classes on Monday mornings and Friday afternoons--before or after the weekends he'd spend with his family in Chicago--which meant he rarely participated in the law school's famous faculty seminars and workshops. This caused a little grumbling among some of his colleagues. "He was at the law school but not of the law school, like Posner and Easterbrook," says Richard Epstein, the famously libertarian law professor. "He's not someone who came to lunch when the topic wasn't one of his choosing." But other faculty said Obama made contributions outside the classroom in other ways. Obama was particularly good at "bonding with students and being a forceful mentor with students," says Baird. "The hours he kept tended to be different. Frank Easterbrook doesn't get up before ten o'clock, where Barack would be there at eight o'clock. Students could have a cup of coffee with him at eight o'clock, and many did."

Obama's closest colleagues at the law school tended to be the more liberal members of the faculty--such as Cass Sunstein and Geoffrey Stone--but many conservatives were fond of him, even though they often didn't see eye to eye. Saul Levmore, the school's current dean, whose politics are hard to characterize but generally right-leaning, says, "We were intensely interested in him. We were looking for him to say, 'I'm giving up politics, I want to be an academic.' We were always in recruiting mode with him." Epstein, who once almost sold his Hyde Park home to Obama and would buttonhole him to talk about things like state mandates for health insurance, offers one reason why: "He was always a terrific listener. He'd sit there and cock his head, take it all in."

Of course, as Epstein points out, Obama's willingness to listen didn't necessarily mean he was willing to be convinced. "What you don't get, alas and alack, out of all this is a change in point of view," Epstein says. "If you ask me whether I had any influence on his intellectual or moral development, I'd say no, not even a little."

But other Chicago conservatives seem content with the fact that Obama tried to understand their point of view, even if he didn't wind up adopting it. "What I know from my dealings with him at the law school is that he does really attempt to understand the points of view of other people who look at the world or a particular issue differently than he does," says Fischel. "He's much more intellectual, much more thoughtful, much more interested in discussion, debate, and dialogue than the typical politician. And that gives me some confidence about him, even though from my perspective he's much too liberal. I've never voted for a Democrat in my entire life. He's the first one I might vote for."

Jason Zengerle is a senior editor at The New Republic.


Subscribe to The New Republic for only $29.97 a year--75% off cover price!