This essay probes the judicial and theological aspects of the conversion of convicted Jewish criminals in central and northern Italy in the pre-Reformation era. First, it delineates the rise in Jewish conversions in the first half of the fifteenth century. It then moves on to the last few decades of the fifteenth century, an era marked by the mounting efforts of Italian ruling elites to display their Catholic piety publicly. In some Italian states, I propose, pardoning convicted Jewish offenders in exchange for their baptism became an important means for achieving this goal. Nonetheless, not all secular authorities were willing to privilege the manifestation of religious zeal over the assertion of their sovereign power to condemn and punish. As documented in the last parts of the essay, in 1491 the issue provoked a vociferous debate in Ferrara and Mantua, featuring the differing judicial stances regarding the earthly implications of the sacrament of baptism.