This chapter is a case study on the letters of Bishop Ambrose of Milan, who borrowed the symbolic capital of the free-spoken court philosopher to create a public persona of an independent bishop speaking truth to power. It discusses the rhetoric of Ambrose’s letters to Emperor Theodosius against the background of the story of their confrontation in the porch of the church of Milan, as it was recounted in later narratives. The chapter analyses the rhetorical strategies that Ambrose employed in his letters to Theodosius to see how these strategies were related to the classical rhetorical tradition of free speech. It shows how Ambrose added Christian elements to the traditional repertoire and associated the duty of the priest to warn rulers from sin with Roman freedom of speech (libertas). Thus, Ambrose firmly connected Christian and classical free speech and offered a model to later generations of free-speaking bishops.