John Rawls was what we might call a “frenemy” to Stanley Cavell. Time and again, Cavell states his admiration for Rawls's political philosophy but criticizes it for two reasons. First, he believes that Rawls too hastily dismisses a perfectionist tradition that is essential for a flourishing liberal democracy. Second, he attacks certain aspects of Rawls's theory of justice as moralistic and legalistic. The first half of this article examines Cavell's critique of Rawls and argues that the two authors are more (...) closely aligned than suspected. It begins by reconstructing Cavell's critique of Rawls, and using archival materials from Harvard University, presents for the first time Rawls's interpretation of this critique. The second half of the article highlights perfectionist themes in Rawls's A Theory of Justice. The contribution of this article is to reevaluate the relationship between two of the most important moral philosophers of the twentieth century and also to provide a more expansive theory of liberalism that incorporates the psychological depth, moral subtlety and political hopefulness of moral perfectionism. (shrink)