This essay is a study in typological exegesis across the testaments of the Christian Bible. Specifically, in light of early Christian conviction that Jesus of Nazareth is the anointed son of David, we seek to understand how the story of David’s violent murder of Uriah the Hittite and rape of Bathsheba figure within a canonical framework in which Jesus is presented as David’s heir and yet also as the one in whom the Davidic legacy of violent betrayal reaches fulfillment. Beginning with a literary reading of David’s sins and their legacy in Samuel–Kings, the essay moves to consider the under-studied reference to Uriah and his wife in the Matthean genealogy and its import for Matthew’s presentation of Jesus as a “son of David.” We suggest that in the gospel tradition, David’s violence concentrates in the obscure figure of Judas Iscariot, who, like Uriah the Hittite, appears last in the roll of individuals faithful to their Israelite king (Matt 10:4; Mark 3:19; Luke 6:16; see 2 Sam 23:39). In contrast to Uriah’s fidelity to David—but in step with David’s betrayal of Uriah—Judas’s treachery demonstrates why typological readings of Jesus as the Davidic heir remain necessarily complex. The Gospels identify Jesus as a new son of David, and in so doing, they also present him as one who transforms that scriptural paradigm through his symbolic reversal of David’s sin.