In his wonderful, revealing feature on Obama's life in Hyde Park--which really should be read in full--Andrew Ferguson got into the question of University of Chicago's conservatism:
Some people call it a college town, since its largest inhabitant, the institution that defines the neighborhood's character, is the University of Chicago, one of the world's most prestigious universities. A friend once described Hyde Park as "Berkeley with snow," and it does indeed have the same graduate-student flavor, the same political activism and boho intellectualism, the same alarmingly high number of men wandering about looking like NPR announcers--the wispy beards and wire rims, the pressed jeans and unscuffed sneakers, the backpacks and the bikes. (This is a pretty good description of William Ayers, by the way.) But the similarities can be overdone. "Not 'Berkeley with snow,' " a U. of C. professor said, when I mentioned my friend's comment to him. "It's the snow that keeps us from being Berkeley. The snow and the cold keep the street people away. It drives everyone inside. You don't have all the students who dropped out of school or graduated and refused to leave. If they stay, they do something. If not, they get out of town. It's too cold just to hang around."
This contributes to the neighborhood's relatively low crime rate and, in part, to the university's reputation as a home for squares and nerds, a buttoned-down "bastion of conservatism," in the phrase of one magazine writer. And the conservatism, by popular account, infects the neighborhood at large, tempers its politics, and adds to its diversity. But the reputation for right-wingery is based on a simple if imprecise bit of data that shocks the delicate sensibilities of college professors: Of the tens of thousands of faculty who have taught at the University of Chicago over the past half-century, perhaps as many as 65 have, at some point in their lives, voted for a Republican. Many of these insurgents were either disciples of the university's most famous faculty member, the free-market economist Milton Friedman, or were drawn to the school because of him; others came under the influence of Allan Bloom, the Straussian philosopher, who ran the university's Olin Center for Inquiry into the Theory and Practice of Democracy, along with a few classically minded scholars. Bloom is dead. So is Friedman. The Olin Center closed its doors in 2005. Their disciples and colleagues who remain at the university aren't getting any younger. It's unlikely that the school's wobbly reputation for conservatism, and the neighborhood's, will survive them.