Although anonymity is a central feature of liberal democracies—not only in the secret ballot, but also in campaign funding, publishing political texts, masked protests, and graffiti—it has so far not been conceptually grounded in democratic theory. Rather, it is treated as a self-explanatory concept related to privacy. To overcome this omission, this article develops a complex understanding of anonymity in the context of democratic theory. Drawing upon the diverse literature on anonymity in political participation, it explains anonymity as highly context-dependent identity performance expressing private sentiments in the public sphere. The contradictory character of its core elements— identity negation and identity creation—results in three sets of contradictory freedoms. Anonymity affords (a) inclusion and exclusion, (b) subversion and submission, and (c) honesty and deception. This contradictory character of anonymity’s affordances illustrates the ambiguous role of anonymity in democracy.