This article locates the ancient debates between Jesus and the Talmudic rabbis within the discourse of contemporary legal theory. By engaging in a comparative reading of both Gospel and rabbinic texts, I show how Jesus and his rabbinic interlocutors sparred over questions we now conceptualize as the central concerns of jurisprudence. Whereas the rabbis approach theological, ethical and moral issues through an analytical, lawyerly interpretation of a dense network of legal rules, Jesus openly questions whether law is the appropriate medium to structure social relationships and resolve interpersonal conflicts. Through an examination of Talmudic sources, this paper argues the controversies between early Christianity and the nascent rabbinic Judaism (summarized by Paul in terms of Letter vs. Spirit) have the same argumentative architecture as the ongoing debates over law vs. equity, procedural vs. substantive justice, rules vs. standards, formalism vs. instrumentalism, and textualism vs. contextualism. Moreover, the contrast between the Gospels and the emerging rabbinic discourse brings Jesus' bold claims about the role, rule and domain of the law to the fore. Thus while the mainstream representation of Christian legal theory tends towards rules, procedural justice, formalism and textualism, this analysis of primary sources shows that Jesus argued for exactly the opposite.