Judgments about the extent to which an individual is free are easily among the more intractable of the various raw materials which present themselves for philosophical processing. On the one hand, few of us have any qualms about making statements to the effect that Blue is more free than Red. Explicitly or otherwise, such claims are the commonplaces of most history textbooks and of much that passes before us in the news media. And yet, good evidence for the presence of (...) a philosophical puzzle here is to be found in the familiar hesitation we experience when we first reflect on the grounds for such claims. Is it really the case that the average Russian is less free than an Englishman in a dole queue? Are we quite certain that a dirt farmer in the Appalachians enjoys greater personal liberty than the inmate of a well-appointed modern prison? Were citizens of classical Athens more free, or less free, than their counterparts in today's welfare states? (shrink)