This chapter explores the profound structural similarities between aesthetic judgement and political judgement, arguing that both rely on analogous mechanisms of deliberation rather than mere rule-application. Drawing on Aristotle’s concept of practical wisdom (phronesis) and Kant’s notion of reflective aesthetic judgement, it contends that political decision-making mobilizes reservoirs of tacit, embodied knowledge akin to those employed in appreciating beauty or artistic merit. The analysis examines key twentieth-century thinkers who argue in favour of this connection. Hannah Arendt interprets Kant’s judgement of taste as a model for political judgement, emphasizing the “enlarged mentality,” imagination, and sensus communis that enable impartial, communicable deliberation, particularly through the distinction between agent and spectator. Hans-Georg Gadamer reverses this approach, deploying Aristotelian phronesis to illuminate aesthetic experience and hermeneutic understanding, highlighting their shared reliance on contextual application and moral knowledge. Michael Oakeshott distinguishes practical from technical knowledge, portraying political activity as rooted in tradition, connoisseurship, and customary practice. Finally, Michael Polanyi’s concept of tacit knowledge underscores the subsidiary awareness integral to skills, connoisseurship, and tradition transmission in both cultural and political realms. Ultimately, these perspectives reveal tacit knowledge as linking politics and culture, grounding the claim that civility emerges as a virtue at their intersection.