Although liberty has been valued in various ways in many times and places, only in Europe did it become a central preoccupation before the nineteenth century, and a subject of widespread public reflection. Appeals to liberty and concerns about it found expression in two idioms: a singular one that harked back to Rome and Greece, and regarded liberty as universal or innate; and a plural one associated with the overlapping jurisdictions of ‘feudal’ society that saw liberty as an assemblage of separate rights or privileges (often taken as synonyms), attributed sometimes to custom and sometimes to higher authorities that granted them. Although distinct, the two languages were seldom seen as in tension before the eighteenth century. The chapter examines their relations in different contexts and concludes by noting that the very pervasiveness of claims to enjoy, embody, or represent liberty led to a recognition of how easily invocations of it could become rhetorical tools to justify control over others, leading to Machiavelli’s incisive reflections on the dialectical relations between liberty and domination.