Adam Smith did not present readers with a theory of freedom per se. He did, however, reflect on prospects for autonomy and self-esteem in market society, inspiring capitalism's critics almost as much as he did capitalism's defenders. In the process he gave us elements of a theory about what sort of freedom market society makes possible, what sort of challenge this freedom represents, and how and why such freedom is (or is not) achieved in particular cases. This essay discusses four such elements: first, market society frees us from starvation; second, market society frees us from servility; third, however, the liberating impact of markets is not guaranteed because markets can be corrupted by crony capitalism (that is, by monarchs and merchants buying and selling political privilege); fourth, markets can fail to be all they should be because of how much people want. Strikingly, the latter worry on Smith's part is not the obvious problem of people wanting too much so much as more subtle problems that go with wanting too little.