Matthew 23:32 is an unsettling text that portrays a moment of profound anger, extreme sadness, and palpable irony. When Jesus’ wish for Jerusalem to repent becomes impossible, he tells its leaders to get on with their plan to do away with him. “Fill up, then, the measure of your ancestors!”This text is like an intersection where four motifs meet head-on.From the Hebrew Bible comes Deuteronomism, which views Israel’s historical destiny as determined by its obedience to the Torah of Moses. Disobedience inevitably leads to judgment. A second, related biblical motif is Israel’s all-too-common rejection of its prophets, God’s messengers who reminded the nation of its covenantal obligations and the consequences of disobedience. The final biblical motif is the notion of sin coming to a head, to a state where God, in order to be God, must act in judgment. To this perfect storm of three biblical motifs Matthew adds a fourth, his own christological hermeneutic: Jesus fulfills the law and the prophets. Just as their ancestors had rejected earlier prophets, so the Jerusalem leaders have rejected Jesus, Israel’s ultimate prophet. Their looming judgment is portrayed as the culmination of a historical pattern or typology of Israel rejecting its own prophets. Yet, just as in the former days when sin led to judgment, repentance can yet again lead to the restoration of God’s favor.