This dissertation examines practical and ethical dimensions of democratic political judgment in the works of Thucydides, Plato and Aristotle. Despite their philosophical and methodological differences, each of these thinkers raised similar doubts about the wisdom of fifth- and fourth-century Athenian decision-making. Arguing that Athenian policy debates tended to privilege short-term gains over longer-term interests, they suggested that moral reflection might guide political judgments toward more ethically sustainable ends. By showing how Greek political philosophy developed in response to real-world political problems, I demonstrate a dialectical relationship between theory and practice that is often overlooked in the scholarship surroundi...