This project examines the treatment of Rome in the writings of Augustine of Hippo and Niccolò Machiavelli. I argue that each thinker's approach to Rome reveals what he believes are the possibilities and limits of necessarily imperfect political life. My dissertation has three substantive parts: the first deals with Augustine, the second with Machiavelli, and the third with larger themes about the relationships between politics, religion, and morality in the writings of these two thinkers and in contemporary politics. Augustine is known for being a sharp critic of Rome, and his antipathy toward the Eternal City is often used to argue that Augustine is disdainful of earthly politics more generally. I challenge the view that Augustine thinks politics in this world cannot be improved and illustrate how he believes the Roman Empire can be used as a means to further Christian ends. Contrary to Augustine, Machiavelli has a reputation for being a great admirer of Rome and for wanting to return to Roman virtues. Yet, even as Machiavelli purports to use Rome as his model, he reinterprets, revises, and even rejects aspects of the Roman example so as to establish and maintain free, secure, and stable political institutions. I aim to tease out the many ways in which these two thinkers, who seem diametrically opposed, actually agree, as well as underscore their fundamental disagreement about the relationship between politics and religion.