The paper focuses on the representation of pedagogical and political communication between (and around) Plato, Dion and Dionysius II in Plutarch's Life of Dion. Plutarch's narrative invokes both the Platonic critique of writing as an inadequate medium for teaching philosophy, and the polarity between free oral speech and writing as a symptom of tyranny. It is argued that the Life espouses but also complicates and implicitly interrogates the opposition between writtenness and orality across the philosophical and the political domain, thus constituting a rich intertextual response, from an Imperial Platonist author, to the Platonic concerns about the written word.