Matthew 23
The Woe Discourse is the most sustained prophetic denunciation in the Gospel — seven woes against the scribes and Pharisees delivered publicly in the temple. Each woe targets a specific form of religious performance that replaces genuine righteousness with public display: not entering the kingdom and blocking others from entering, devouring widows' houses while making long prayers, making converts twice as fit for hell as themselves, swearing by the gold of the temple rather than the temple that makes the gold holy, giving the tithe of spices while neglecting justice and mercy and faithfulness, cleaning the outside of the cup while the inside is full of greed and self-indulgence, appearing righteous while being full of hypocrisy. The chapter closes with the lament over Jerusalem — how often I have longed to gather your children as a hen gathers her chicks under her wings, but you were not willing — and the announcement that the house will be left desolate until the day they say blessed is he who comes in the name of the Lord.
Matthew 23:39
For I tell you, you will not see me again, until you say, blessed is he who comes in the name of the Lord. The departure and the future return: you will not see me again until you say blessed is he who comes — the Psalm 118:26 Hosanna that the crowd shouted at the triumphal entry. The until communicates the eschatological hope: the seeing will come again, when the generation that rejected him welcomes him as the crowd of the triumphal entry did. Romans 11:25–26 holds the same hope: Israel's partial hardening will end when the fullness of the Gentiles has come in.
Matthew 23:26
You blind Pharisee! First clean the inside of the cup and the plate, that the outside also may be clean. The order of cleansing: inside first, then the outside will also be clean. The teaching of Matthew 15:11 (what comes out of the mouth defiles) applied to the Pharisees directly: the inside that is cleaned produces the outside cleanness that the ritual purity system seeks by external means.
Matthew 23:32
Fill up, then, the measure of your fathers. The ironic imperative — fill up the measure — communicates the inevitability of the path they are on: they will complete what their fathers began by killing the prophets. The they are about to kill Jesus confirms the irony: the tomb-builders are becoming the prophet-killers.
Matthew 23:33
You serpents, you brood of vipers, how are you to escape being sentenced to hell? The serpents and brood of vipers — the same epithet John the Baptist applied to them (Matthew 3:7) — are the climactic indictment. The how are you to escape being sentenced to hell is the question that the seven woes have been building toward: the judgment that the Pharisees' hypocrisy has accumulated cannot be escaped.
Matthew 23:34
Therefore I send you prophets and wise men and scribes, some of whom you will kill and crucify, and some you will flog in your synagogues and pursue from town to town. The sending of prophets, wise men, and scribes — the messengers of the kingdom — who will be killed, crucified, flogged, and pursued by the religious establishment. The future tense communicates the ongoing pattern: the Pharisees who killed the prophets will continue to kill the prophets. The followers of Jesus will suffer what Jesus suffered.