This essay explores what Thucydides teaches about leadership, by focusing on four prominent leaders in his History: Pericles, Brasidas, Alcibiades, and Nicias. Successful leaders operate within the confines of particular cities, regimes, and their ways of life, but find space for freedom by articulating goals and standards for action. Pericles instructs Athenians about their city’s purpose and its demands, while presenting himself as a model of freedom. Brasidas represents Spartan dedication to freedom from oppression, but to the larger world rather than to the Spartans themselves. Alcibiades carries Athenian freedom to the point of betraying cities, and Nicias betrays that freedom by refusing to exercise it. Leadership demonstrates that freedom is possible for human beings, but that it must be cultivated by leaders themselves. Thucydides judges leaders by their success in doing so.