Jacques Derrida had never written a book on "freedom." This word occurs very rarely in his writings until the late '80s; since then, he had increasingly employed it, but with circumspection. In this article, I aim to show that we can trace a thinking of freedom throughout Derrida's work and that this thinking describes a singular trajectory from the subjective freedom of the humanist history of life to the presubjective freedom of symbolic life. To this end, first, I shall explore Derrida's early deconstructive reading of the conception of subjective freedom that underpins modern philosophical and biological accounts of the living. Second, I shall focus on the conception of the other's freedom that Derrida finds at work in the symbolic machine of sovereign decision. The turning point of this trajectory, I shall argue, is the elaboration, proposed by Derrida in the late '80s, of an experience of freedom as nonknowledge that is neutralized by and yet exceeds subjective and sovereign freedom.