This chapter distinguishes three positions that are commonly regarded as liberal in contemporary philosophical discussions. They are classical liberalism, libertarianism, and the left-liberal position that is termed as 'the high liberal tradition'. One way to understand liberal libertarianism that perhaps renders the term non-redundant is that it represents the position of those classical liberal philosophers who, if given the choice, would endorse orthodox libertarianism as a second best arrangement of society, ranking it above high liberalism. The primary difference between orthodox libertarian and liberal views is the conception of absolute property and unrestricted contract rights grounding the former. Self-inflicted slavery, or transforming oneself into someone else's property for legal purposes, is an example of this more general problem with orthodox libertarianism. For liberals, it is precisely because political power is a public fiduciary power that is not to be exercised contrary to the public good that liberal governments refuse to coercively enforce or permit the private enforcement of unconscionable contracts.