How is freedom tied to tradition? What is the relation between the individual and the collective experience of tradition? To what extent is the experience of tradition part of a modern experience rather than only of an ancient one? This essay argues that these questions lie at the heart of Walter Benjamin’s early discussion of tradition. His peculiar reference to “Talmudic wit” and to Kant as a tradendum in letters to Scholem, alongside related Jewish sources, and his engagement with Kant in “On the Program of the Coming Philosophy” are used to address these questions. Thus the essay offers a concept of tradition as a transformative medium that prefigures Benjamin’s late and familiar inkling for tradition’s revolutionary potential. Additionally, it suggests that in this context an alternative to Kant’s concept of freedom is prefigured.