It is a well-known fact that the pontificate of Gregory the Great (590–604) stands at a time of transition between Late Antiquity and the Early Middle Ages. 1 Above all things, Gregory sought to preserve the proper ordering of creation with its associated trinitarian understandings. In practice, his activity as pope may be examined from a number of perspectives. In choosing that of Sicily, one is presented with a world in microcosm in which certain social groupings emerge as being of particular significance. 2 These, in turn, became the source of several priorities within the papal administrative system as it developed under Gregory. His relations with and shaping of the local Sicilian bench of bishops is of major significance for his activity elsewhere in the church. His use of administrators (rectores, defensores, etc.) to manage the affairs of the Sicilian patrimony of the Roman church gave expression to what was to become a recognisable system of Roman church governance throughout the Middle Ages. His relations with Byzantine officials charged with the imperial government of the island (the praetor Siciliae and his retinue) provide a glimpse into the association between church auctoritas and state potestas within the context of a wider world in Late Antiquity.