In this dissertation, I contend that the growing disenchantment with public institutions in Western democracies and the popular desire for leaders perceived to be of good moral character both justifies and calls for an investigation of the Western tradition of political philosophy to determine which, if any, models of virtuous statesmanship in that tradition may serve as a useful model of virtuous leadership for our own time. I evaluate four models of magnanimous statesmanship as presented by four of the most influential political philosophers in our tradition: Aristotle, Cicero, Thomas Aquinas, and Machiavelli. I examine the relationship between these thinkers' conceptions of magnanimous statesmanship as well as each of their conceptions of this virtue on its own terms. I conclude that Cicero had a far greater influence on both Aquinas's and Machiavelli's understandings of this virtue and, more broadly, on statesmanship than generally thought, and I further conclude that Ciceronian magnanimity offers liberal democracies a useful model of magnanimous statesmanship apart from any commitment to virtue ethics or teleology.