By the time Gregory the Great (590-604) began his ministry as bishop of Rome, the political, economic, and social circumstances in Italy were dire, as evidenced by ongoing barbarian threats, Rome’s failing infrastructure, monuments and aqueducts in need of repair, abandoned farms, and decimated populations. As a result, demands were made on Gregory to tend to both the spiritual and physical needs of the people in Rome and in Italy. I argue that through his actions and writings, Gregory took control of the situation, and transcended pre-established ecclesiastical policies and procedures that permitted religious authorities to enter into political affairs. An examination of the fourth-century paradigm of Ambrose, bishop of Milan, and the fifth-century paradigm of Leo the Great, bishop of Rome, introduces earlier examples in which pastoral leaders became active in state matters. Gregory, while not explicitly stating their influence on him, goes beyond them both and develops a paradigm uniquely his own. Gregory’s eschatology significantly shaped his understanding of the need to be involved in both religious and political matters. In analyzing his Pastoral Rule, Moralia, and homilies on the Gospels and the Prophet Ezekiel, I have identified the virtues and qualities that Gregory felt all pastoral leaders must possess. The resulting profile of leadership emphasizes the moral conduct and the intentionality that those in authority need to operate. Through examining a large selection of his letters, I have been able to present a political theology that was key to Gregory’s entrance into political affairs and his development of social programs that tended to the physical needs of the people. I conclude that Gregory’s profile of leadership and political theology reveal a new paradigm which is his contribution to the ongoing development of the relationship between the Church and the state as both emerge from the age of late antiquity.