Whenever I say nice things about Canada, some people get annoyed. After all, they have socialized medicine and are more inclined to regulate certain kinds of speech. But these are anecdotes. If looks for anecdotes on the lack of freedom in the U.S., one becomes buried in them. If I look at actual indices that attempt, however imperfectly, to measure various freedoms, the U.S. and Canada come out pretty much identical on a classical liberal conception of freedom. And Canada comes out ahead on contemporary capabilities conceptions of positve liberty. To my mind, the evidence pretty strongly supports the conclusion that Canada is at least as free as the United States. Why is this a problem for some Americans?
It's true that the U.S. has in many ways a more libertarian culture and political tradition than does Canada. But then isn't it all the more interesting to note that, despite America's unique “land of the free” self-conception, we're no more free than Canadians? I feel strongly that American culture is more varied, alive, weirder, synthetic, and creative than probably any other. This is in part because of, and not despite, the odd conservative and religions strands in American culture. And it is a culture especially amenable to all sorts of entrepreneurial experiments, which gives American culture a level of innovation and vitality (including countless varieties of religious weirdness) that I think partly explains why it is the world's dominant exporter of culture. And I think the U.S.'s wealth relative to other countries is actually underestimated. We are astoundingly rich (recession or no recession) and this is a place of crazy opportunity. So I think the U.S. does better in positive liberty terms than it sometimes gets credit for.
But that doesn't begin to mean that we live up to our reputation for the kind of liberty classical liberals tend to care about. My sense is that some American libertarians have a vague sense that if Canada really was more free, then they should want to move there. But they emphatically don't want to move to Canada. My diagnosis is that many libertarians prefer to live in a place where it easy to find others who share their individualistic and libertarian values over living in a place where they would actually be more free, but would feel more culturally alienated.