In order to understand the educational objectives of Machiavelli's *Discourses on Livy*, one must study Augustine's *City of God*. Particularly, one must study Augustine's treatment of Rome and the problem of corruption (political, physical and spiritual) that Augustine treats through his analysis of the Ancient Republic and Empire. A key intention of Machiavelli's "new modes and orders" is to re-portray Roman *virtù* over and against the Christian virtue of Machiavelli's age, in such a manner that one's otherworldly commitments do not interfere with the political stability of the city. To elucidate this point, I begin with an analysis of Augustine's account of corruption and finitude and its implications for political life. I turn next to Augustine's treatment of four Roman heroes — Lucretia, Romulus, Regulus and Brutus. I then turn to Machiavelli's use of rituals and other institutions, which parallels Augustine's use of rituals, and how Machiavelli uses these institutions and rituals to solve the problem of corruption. In the following chapters I treat the four Roman heroes Lucretia, Romulus, Regulus and Brutus from the perspective of Machiavelli. I conclude with reflections on problems with Machiavelli's account of human psychology that impede his political conclusions.