In this dissertation, I consider three interrelated questions. First, what would a good democratic leader be like? Second, what sort of education would such a leader require? Third, is such an education even possible? In an attempt to answer these questions, I turn to the ancient Greek political thinkers Thucydides and Plato. In particular, I consult Thucydides's account of the war between Sparta and Athens and two of Plato's dialogues, Laches and Alcibiades I, in order to trace out the competing answers which Thucydides and Plato's Socrates give to the questions I have raised. I conclude that while Thucydides and Socrates consider many of the same themes in their accounts (such as the common good, political speech, self-knowledge, the virtues of statesmanship, and the distinctiveness of democracy), they often treat these themes in different, sometimes even incompatible, fashions. I conclude that the root of many, if not all, of these differences lies in Thucydides's willing acceptance and Socrates's insistent rejection of the common sense of ordinary political life.