Being put on the couch
My friend Todd Seavey-- with whom I have a twenty-year morphing-but-running argument about the relationship between libertarianism and (variously) liberalism and conservatism as systems of ideas, liberalism and conservatism as organized political movements, the American Democratic and Republican parties-- offers an analysis of why I (among other libertarians he knows) certainly won't vote for McCain and will probably vote for Obama. It's odd to see oneself analyzed as a phenomenon, but I do think he's right about me and the Iraq War. I was basically in support of the war, I was wrong, and I give Obama credit for having been right and McCain discredit for seeking to double down on the wrongness. (I've never written a big mea culpa post about it, but Dan Drezner and Belle Waring have written posts that happen to do a very good job of speaking for me-- both in what I was thinking in 2002 and in what I came to think since.)
As far as the Chicago connection goes, there may well be some added comfort on my part with Obama, whom I've never met, because of all the people I know and respect who know and respect him. Sunstein is certainly on that list-- but so are a lot of other people at the University of Chicago Law School whose politics are much closer to Todd's and mine than they are to Cass'.