This paper offers an alternative defense of private economic liberty to the account set forth in John Tomasi’s Free Market Fairness. In Pennington’s endorsement of the ideal of a classical-liberal minimal state the practical/normative implications of his analysis differ very little from that set forth in Tomasi’s book. The character of the reasons given in defense of this ideal however, differ markedly from Tomasi’s favored approach. Instead of building a case for economic liberty based on its contribution to self-authorship under highly idealized conditions, Pennington maintains that the strongest arguments for classical liberalism rest on a “realistic idealism” which examines the significance of compliance problems in a comparative political-economy framework. Specifying the practical boundaries of this idealism requires that issues of feasibility and compliance be brought to the forefront of normative theory. They cannot be discovered by assuming away the most fundamental problems of political economy.