In this essay, I reconsider the constitution of democratic freedom in aesthetic terms. My interest is in articulating a conception of aesthetic freedom that can be mapped onto a conception of democratic freedom. For this purpose, I bring together Charles Sanders Peirce’s ontology, which comprises fragments of an aesthetic theory, Friedrich Schiller’s concept of aesthetic play and Stanley Cavell’s democratic perfectionism. By providing a philosophical framework for constructing an aesthetics and politics that supports the recent aesthetic turn in political theory, (...) which urges overcoming political theory’s excessive dependence on an epistemological theory of representation, and by proposing a modification to the turn’s heavy reliance on theories of affect, my reading of Peirce, Schiller and Cavell offers a new way to think about the political significance of the autonomy of aesthetic experience and affect for democratic freedom. (shrink)