Plato and Xenophon had different perspectives on the better governance. In this paper, I study the notion of tyranny in Plato's Republic and Xenophon's Hiero to trace their views on the aptitude of philosophy to redeem the tyrant and indicate some intertextual points. On this basis, I analyse the meaning and extent of Simonides’ proposal in the Hiero rejecting the idea of a mere pragmatic approach. Finally, I examine the platonic Hipparchusto find a key to figure out the election of (...) Simonides as Xenophon’s spokesperson. Paying attention to the context of the discussions among the Socratics, this approach enhances our understanding of these authors, regarding tyranny, the possibility of its abandonment, and the role of the intellectuals in this process. (shrink)