The critical theory tradition has, since its inception, sought to distinguish its perspective on society from more purely descriptive or normative approaches by maintaining that persons have a deep-seated interest in the free development of their personality—an interest that can only be realized in and through the rational organization of society, but which is systematically stymied by existing society. Yet it has struggled to specify this emancipatory interest in a way that avoids being either excessively utopian or overly accommodating to existing society. Despite the fact that Hegel’s concept of reconciliation is normally thought to run aground on the latter horn of this dilemma, this book argues that reconciliation is the best available conceptualization of this emancipatory interest. It presents Hegel’s idea of freedom as something actualized in individuals’ lives through their becoming reconciled to how society shapes their roles, prospects, and sense of self; it presents reconciliation as being less a matter of philosophical cognition, and more of inclusion in a responsive, transparent political process. It then introduces the concept of reification, which—through its development in Marx and Lukács, through Horkheimer and Adorno—substantiates an increasingly cogent critique of reconciliation as something unachievable within the framework of modern society. Giving equal attention to psychoanalysis and legal theory, the second half critically appraises the writings of Rawls, Honneth, and Habermas as efforts to spell out what a concept of reconciliation more democratic and inclusive than Hegel, yet sensitive to the reifying effects of legal systems, might mean.