This essay uses William Shakespeare’s Measure for Measure, based on a novella by Gimbattista Giraldi Cinzio, to examine what it means for Shakespeare to stage narratives engaged in Italian Roman law within England’s common law system. The essay analyzes Measure for Measure as an exemplar of the cross-cultural legal exchanges in the numerous Italian stories depicted on the English stage. Within this comparative framework, Shakespeare builds from Italian social experience in Cinzio’s novella and Niccolò Machiavelli’s political discourse to critique the shift from local to state legal authority occurring throughout sixteenth-century England. Specifically, Shakespeare’s Measure for Measure challenges commanding perceptions of communal justice fundamental to English legal ideology and reveals law’s theatrical power. Using Shakespeare’s play as a case study, this essay further illustrates how transnational literature both contributes to popular early modern conceptions of law and uncovers power dynamics behind the development of legal systems.