The paper will examine the incarnation of Kant’s Critique of the Power of Judgment as a model for political judgment, notably in Hannah Arendt’s interpretation. It will highlight the elements in Kant’s analysis of the judgment of the beautiful that have served to nourish some contemporary notions of political deliberation. The pitfalls and potential promise of transposing an aesthetic appreciation to the political realm will also be considered. In Kant’s view, aesthetic judgment is profoundly subjective, grounded in the feeling of pleasure or displeasure. Taste is a personal matter. It is, however, communicable since it arises from a form of judgment. In judgments of taste, pleasure and displeasure are not pure sensation; they are reflected feelings. The judgment of the beautiful has the distinct particularity, according to Kant, of including others in the very judgment. The perception is never purely solitary; it accounts for others in how the object is viewed. Absent any possibility of defining beauty objectively, this underlying and implicit dimension is what renders the experience of beauty communicable. One might say that the private experience of pleasure through the faculty of judgment is immediately also potentially inter-subjective as well as communicable. It is precisely these specific features, the inter-subjective experience and its communicability, that have inspired contemporary political thought in thinkers such as Arendt, Habermas, and others. Whether the genesis and finality of these features reside in judgments of taste or in cognition remains contested and open to question.