Plato's confrontation with Dionysius I, the so-called “tyrant of Sicily,” became famous as a cautionary tale of the perils of offering unwelcome advice to a powerful prince. Within early modern England, this tale took on added currency in the context of humanists' ambitions to serve as counselors in the court of Henry VIII. The humanist scholar Thomas Elyot, who briefly and unsuccessfully served at Henry's court, re-created Plato's exchange with Dionysius I in his dramatic dialogue The Knowledge Whiche Maketh a (...) Wise Man. In his dialogue, Elyot imagines Plato returning to Athens after his brief period of enslavement, where he meets the philosopher/rhetorician Aristippus. Aristippus challenges Plato by positing that Plato's dangerous words to Dionysius violated rhetorical tenets of propriety and timing. In the course of their extended exchange, two different versions of the rhetoric of counsel surface—one based on principles of philosophy and one based on strategic rhetoric. (shrink)