The history of political freedom in Europe has long been articulated within a genealogical scheme that interprets the nature of contemporary freedom starting from its remote origins. This explains the adoption of a teleological approach: from the freedom of the ancients to that of the moderns; from positive to negative freedom; from libertas ecclesiae to religious tolerance. Awareness of the crisis of the great narrative of freedom invites us to broaden the field of analysis, rejecting a linear history of the notion and its expressions, less and less capable of accounting for the discontinuities and tensions between different meanings and models. The volume reintegrates the theme of freedom within the framework of the practices of political actors in the late Middle Ages, taking into consideration the multiple declinations of the ideas of freedom in Europe with a specific attention to the Italian realities.