Cicero’s orations show versatility in adapting to new situations and contexts during the latter half of his career, particularly in his reshaping of these paradigmatic roles as a political orator. Studying these roles allows us to appreciate the complexity and flexibility of his self-fashioning over time, independently of chronological phases. He chooses his personae to suit the circumstances of each case and selects from a range of possibilities in confronting those circumstances, calculating for maximum advantage. Each persona requires balance and care to avoid extremes. Caesar, Pompey, Clodius, and Antony presented obstacles to politics as usual – or, at least, to norms for political processes as traditionally conceived – which could not be ignored, and which had to be negotiated carefully and creatively. Cicero was successful in doing so, up to a point.