Last night I started working on a post that was going to conclude that Obama is easily the most libertarian of the viable candidates in either party's race (the Ron Paul newsletters obviously being a disqualifying factor for him in my book). I was hoping to have it finished tonight. Unfortunately for me, it looks like I was beaten to the punch in this Daniel Koffler piece at Comment is Free. Maybe I'll still provide my arguments at a later point in time, which are centered on the idea that free market economics should be less important this year than personal and civil liberties. I loosely started to sketch this point in the second half of this post.
In any event, money quote from the Comment is Free piece:
Goolsbee and Obama's understanding of the free market as a useful means of promoting social justice, rather than an obstacle to it, contrasts most starkly with the rest of the Democratic field on issues of competition, free trade and financial liberalism.
Is it possible that Obama is really a libertarian in a Progressive's clothes? Doubtful. But I have long thought that Obama's relationship with Austin Goolsbee was extremely promising compared to traditional Dem candidates, and even Republican candidates these days. Even Ron Paul would not end the welfare state over night; Obama's policies at least aim to end or reduce the welfare state at some time down the line by ultimately eliminating the need for that welfare state.
Bottom line: Koffler makes a pretty strong argument that Obama is more sincere about individual freedom and ending coercion than just about any other candidate on either side. Given their differences on federalism and immigration, you might even argue that Obama is a firmer believer in individual liberty than Ron Paul. I don't know if that's a winning argument, but it's not a laughable one either.