This chapter explores the ambiguities in power dynamics that arise in Paul’s letters when enslaved persons enact religious leadership in the communities to which he wrote. The chapter demonstrates that 1 Corinthians, Galatians, and Philemon illustrate a debate about roles in the communities to which they are addressed, particularly the ongoing debate about whether enslaved persons are fully equal members of the ekklēsia or whether their experiences in slavery are problematic for communal ethics. The chapter examines the rhetoric of these letters, exploring the different stories scholars tell about Paul and slavery. The chapter shifts the methodological focus so that enslaved persons become the center of the story rather than Paul. Ultimately, the chapter argues that early Christian rhetoric continually subordinates enslaved persons because of the contestations of power that arise when enslaved persons act as full participants, even trained leaders, in early Christian communities.