The purpose of this chapter is to offer a sketch of the relation between rhetoric and dialectic as Cicero sees it, and to identify a problem internal to his account. Cicero argues at length in the Tusculan Disputations in favor of the idea that the good and wise person does not experience any form of emotional disturbance. That being so, how can one who signs up to the idea that emotional disturbance is ideally to be eliminated then in good conscience recommend a practice – namely, rhetoric – one of whose principal objectives is to arouse the emotions? There looks to be a clash here between the objective of the philosopher and that of the orator. I explore Cicero’s resources for tackling this tension, and suggest how his conception of the relation between rhetoric and dialectic may thereby illuminate some distinctive aspects of his philosophical approach.