Machiavelli assigns a complicated role in his political theory to the concept of the beneficium (or benefizio in Machiavelli’s Italian) in order to describe the benefits that the power of the state can bring; and this chapter focuses on one philosophical language which is used throughout the Italian Renaissance to discuss this idea and which comes to shape Machiavelli’s own thinking decisively. That language is classical in origin; and it is intimately associated with one text in particular: Seneca’s On Benefits. In the first section of the chapter, Seneca’s thinking about generosity and gratitude is explicated within the wider context of his social philosophy to show how it forms part of a theory of moral obligation, informed by a firmly Stoic notion of natural human sociability. The second section shows how Seneca’s contentions are subsequently retrieved and put to work in pre-humanist and humanist political thought to discuss the moral relationships between members of civil associations and to underline the perils of the vice of ingratitude in political society. Once the place of Seneca’s theory in Renaissance discourse is elucidated, it becomes easier to see how Machiavelli manipulates its contentions into a theory of political obligation within his account of the state.