Ambition, which is essentially the passion to be held superior in the eyes of others, stands in an uneasy relationship with leadership. It is certainly true that this passion can be a powerful force motivating people into leadership roles. Yet the consequences of this dynamic of the human soul are not always, and certainly not necessarily, promising for humankind. This Element investigates the leadership element of ambition through analysis of three key humanities texts: Tocqueville's Democracy in America, Xenophon's Education of Cyrus, and Plutarch's Life of Alcibiades. Through a close reading of these works, the Element sheds light on the nature of ambition and its impact on leadership, especially the way in which ambition operates differently according to the context of the regime.