This chapter explores the relationships among Cicero’s three pre-Civil-War dialogues, De oratore, De re publica, and the incomplete De legibus, both in terms of their relationship to Plato and in terms of their connections with one another. While some important recent scholarship has emphasized the links between De re publica and De legibus, I concentrate on the links between De oratore and De re publica, in terms of their attitudes to Plato and to Hellenistic learning, the relationship they establish between Greek thought and Roman practice, and their construction of the interrelated histories of philosophy, rhetoric, and politics. I also suggest that De legibus is strikingly different from the other two works in these respects and also in the relative weight it places on the role of individuals and institutions in creating a moral and successful public world.