In this article, John F. Covaleskie considers a threefold question: (1) what is the nature of the sort of liberty that enables one to live as a free person, but also bound by the requirements of democratic citizenship; (2) what is the nature of the virtues that make this sort of person possible; and (3) what is the nature of the educational experience that helps foster the virtues that make that sort of person? The concern at the heart of this essay is to recall John Dewey's emphasis on the importance of discipline in the realization of democratic life and democratic education. An important part of this essay is to reflect on the relationship between democracy, virtue, and discipline. These terms are contested and ambiguous, and a large part of my purpose is to examine how they relate to each other in the context of Dewey's view of democracy and democratic education. The first section of the essay considers the distinctive nature of Deweyan democracy and its relation to a substantive idea of a common good; the second section discusses the the requirement for virtue of the citizens of any democratic polity; and the third section briefly considers the pedagogical implications of the understanding of democracy discussed here.