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This article will examine the development of John Milton's arguments for democracy as against monarchy and other sorts of autocratic rule. These arguments are interesting both in their own right and insofar as they shed light on historiographical debates concerning the classical republican tradition. Milton is shown to hold a negative conception of liberty, as opposed to a positive or participatory conception, which lends support to the neo-roman interpretation of that tradition, associated with Quentin Skinner and Philip Pettit. However, it is further shown that Sinner and Pettit misunderstand the classical republicans' case for democracy, attributing to them a conceptual argument in place of an empirical one. A better understanding of Milton's political theory contributes to a better understanding of this dilemma, and perhaps suggests a solution.