This paper examines the differences between moralist, realist, and pragmatist approaches to political legitimacy by articulating their largely implicit views of judgment. Three claims are advanced. First, the salient opposition among approaches to legitimacy is not between “moralism” and “realism.” Recent realist proposals for rethinking legitimacy share with moralist views a distinctive form, called “normativism”: a quest for knowledge of principles that solve the question of legitimacy. This assumes that judging legitimacy is a matter of applying such principles to a case at hand. Second, neither Rawls nor Habermas is a normativist about political legitimacy. The principles of legitimacy they proffer claim to express rather than adjudicate the legitimacy of a liberal-democratic regime, and thus cannot solve the question of legitimacy at a fundamental level. But perhaps we should question the normativist aspiration to theoretically resolving the problem to begin with. My third claim is that a “pragmatist” approach enables us to rethink political legitimacy more deeply by shifting focus from the articulation of principles to the activity of judging. Implicit in Rawls’s and Habermas’s theories I then find clues towards an alternative account of judgment, in which the question of legitimacy calls not for theoretical resolution but for ongoing practical engagement.