Discussion of the confrontation between Socrates and Callicles in the Gorgias has mostly focused on its first two phases: Callicles’ statement of his views and Socrates’ attempted refutations (481–500), and Socrates’ subsequent attempt to substitute his own conception of the good life (501–9). Much less attention has been paid to the final phase (509–22). But Plato stages here the most sustained debate in the dialogue between alternative answers – with their consequences – to what has proved to be its central question: is committing injustice or falling victim to it the greatest evil? This chapter examines the key moves in this debate, in which Callicles is again tempted by Socrates to participate, after previously refusing to continue. I argue that Plato’s aim here is to show just why and how Socrates might successfully initiate and sustain intellectual engagement with an intelligent young politician hoping to rise within the Athenian democracy, such as Callicles is portrayed as being. He fails to persuade him. But this is not, as sometimes supposed, a failure of intellectual communication. It is a matter of what Plato wants us to understand as different fundamental commitments.