The theatrical capital punishments of the early modern period blurred distinctions between private and public and between object and subject in their treatment of the prisoner’s body. Where did these rituals originate? Italian confraternities devised distinctive forms of offering spiritual comfort to the condemned through the fourteenth and fifteenth centuries that mediated new uses of the prisoner’s body in civic religious ritual, in literature, and in the justice system itself over the sixteenth and seventeenth centuries. Almost all changes of the later period were incremental adaptations that deliberately projected a continuity of tradition, with place, space, and ritual carrying critical symbolic resonances. Considering how confraternal comforting rituals employed the prisoner’s body as a sacramental object, as an artistic and literary object, and as a political object can peel back the early modern layering of new religious, cultural, and political meanings in execution rituals. Using the two cities of Florence and Bologna as examples of the process, this essay demonstrates that the layerings did not develop in a clear sequence, but accumulated in a paradoxical interrelation governed by local political conditions.