This article develops some conceptual correlations between Kant’s theory of aesthetic judgment and the common law tradition of legal judgment. The article argues that legal judgment, like aesthetic judgment, is best conceived in terms of intersubjective validity rather than objective truth. Understanding the parallel between aesthetic and legal judgment allows us to appreciate better the relationship between subjectivity and intersubjectivity, the individual and the community, in the formulation and communication of judgments, which combine a personal response and a reasoned determination intended for a discrete audience. The article frames and pursues these themes in relation to four core concepts in Kant’s aesthetic theory: judgment, communication, community, and disinterestedness. Through sustained comparison and application of these concepts in aesthetic judgment and legal judgment, the article provides a conception of judging that more accurately captures the common law role and relationship of the individual judge and the institutional judiciary as integral parts of the broader legal and political community.