This paper has several aims. Its main interpretive task is to argue that the democratic aspirations of contemporary critical theory are informed and haunted by an essentially Hegelian conception of constitutional order that I describe in part 1, according to which the modern state represents an institutional structure that integrates society through rational activity by mediating between the different interests of various social strata, connecting them in a common enterprise—haunted, because this Hegelian vision of making individuals free and “at home” in the modern world, reconciled to it by virtue of being able to comprehend their social order as the work of their own shared reasons, remains a griping one, but one that critical theorists starting with the Left Hegelians view as increasingly implausible under modern social conditions. In section 2, I trace the decline of confidence in the prospects for the rational/mediational integration of society Hegel envisioned through Horkheimer and Adorno, and discuss some relevant aspects of Habermas’s initial reception of their views. Section 3 argues that the conceptions of democratic constitutional politics offered by Habermas and Benhabib should be read as attempts to recover, in a critical manner and under changed conditions, Hegel’s idea of social order as the product of rational activity. Along the way, I will make three interpretive and critical points: first, the existence of this link to Hegelian conceptions of constitutionalism demonstrates that interpretations of Habermas’s later work that read him as having broken with the tradition of Left Hegelianism are overstated—my reading of Habermas highlights his essentially Hegelian proceduralism and the social theoretic dimension of his work, and should challenge people who think of him as a neo-Kantian moralist. Second, this Left Hegelian social theoretic backdrop provides a stronger normative justification for the practice of democratically rearticulating constitutional norms—along with its apparent demotion of the stabilizing virtues of the rule of law—than the contextual one that some legal theorists have so far offered. Thirdly, I will comment on the shortcomings of Habermas’s conception of democratic constitutionalism, as well as Benhabib’s modified concept of “democratic iterations,” along with some brief suggestions on how this set of ideas should be developed.