Summary: A warning not only for Israel then, but for the church now. The long-suffering of God.
1. Jesus spares not to warn those who are on the path to “the damnation of hell” (Matthew 23:33), using such expressions as “woe unto you” (eight times), “hypocrites” (seven times), “blind guides” or “fools and blind” (five times), “ye serpents, (ye) generation of vipers” (once).
Matthew 23:13. The 1st “woe” is against those leaders who not only refuse the offer of the gospel for themselves, but also prevent others from following Jesus. Their equivalent today will try to talk ‘born-again’ Christians out of their new-found faith, no doubt intimidated by their enthusiasm. Their own religion is cold and formal and dead, and the last thing they want is outsiders coming into ‘their’ church and upsetting the status quo.
Matthew 23:14. The 2nd “woe” challenges a certain covetousness practiced under cover of supposed prayerful ‘holiness’. Some Scribes and Pharisees “devour widows' houses” warned Jesus. The Scribes were the lawyers of their day, supposedly applying the law of Moses: but were they perhaps condoning a system of religion in which the widow was a victim, giving her last penny to line their pockets (cf. Mark 12:42)?
“And for a pretence they make long prayers. These will receive greater condemnation.” Jesus teaches elsewhere that those who pray ‘to be seen of men’ (Matthew 6:5) ‘have their reward’ - in other words, their prayers will not reach heaven, but only the ears of the men they are seeking to impress. And as for the length of our prayers, they should lack the ‘vain repetitions’ and ‘many words’ by which ‘the heathen’ think they will be heard (Matthew 6:7).
Matthew 23:15. The 3rd “woe” is against a misplaced zeal to recruit, not for the kingdom of God, nor for the greater good of the recruit’s soul, but only for the furthering of a particular sect. The half-trained proselyte of a cause is “twofold more the child of hell” than his recruiters, says Jesus.
Matthew 23:16-22. The 4th “woe” concerns fussing about oaths. Jesus’ earlier teaching was, ‘swear not at all’ (cf. Matthew 5:34-37). There is no ambiguity in the directive about swearing: Jesus is rather emphasising straightforward, honest speaking. Do not commit perjury, and do not be always dragging the Lord’s name and the things of God - and this and that - into our private assertions. If we are Christians, our word should be enough (cf. James 5:12).
Matthew 23:23-24. The 5th “woe” reflects upon a certain petty scrupulosity in small things coupled with a neglect of the “weightier” matters of “justice, mercy and faith” (cf. Micah 6:8). The Pharisee boasted, ‘I fast twice a week, I give tithes of all I get’ (Luke 18:12). But what good is all that if we lack the ‘fruit of the Spirit’ (Galatians 5:22-23)?
Matthew 23:25-26. The 6th “woe” challenges a religion which is merely external. There is no point putting on our best Sunday clothes, and our best Sunday face, if “within” we are full of “extortion and excess.” What defiles comes from “within” (cf. Matthew 15:19-20).
Matthew 23:27-28. The 7th “woe” exposes the veneer of a decaying religion, which is outwardly “beautiful” but inwardly “full of hypocrisy and decay.”
Matthew 23:29-33. The 8th “woe” exposes the hypocrisy of the Pharisees in honouring the prophets of old whilst at the same time plotting against Jesus, the Messiah to whom the prophets were pointing! “Fill ye up then the measure of your fathers,” scolds Jesus.
2. “Wherefore,” begins Matthew 23:34-36 - literally, “Because of this.” “Because” you are in such a state of woe, “Because” you are on the road to hell, “behold I send unto you prophets, and wise men, and scribes.” However, you will kill these too, so that “all the righteous blood shed upon the earth” may be filled up by this generation.
There seems to be an inevitability about this, but Jesus is still reaching out the olive branch. The nation still had as much as “a generation” (c. 40 years) to repent. The Jewish mission would continue after Jesus’ resurrection and ascension into heaven, at least as long as the Temple still stood. No-one may complain about any lack of ‘long-suffering’ on the part of God (cf. 2 Peter 3:9)!
This has been a hard chapter to read, but God did not give up on Israel, even then. Neither has He given up on us. Jesus longs to gather to Himself both those teachers thus reproved, and their followers: but they “would not” (Matthew 23:37). It is all a matter of the will: “I will,” says Jesus, “but you will not.”
So, with tears in His eyes, Jesus’ final word to the Pharisees, and to Jerusalem, is, “Behold your house is left unto you desolate” (Matthew 23:38; cf. Matthew 24:2). That is, “Till ye shall say, ‘Blessed is He who comes in the name of the Lord’” (Matthew 23:39). There are still promises for Israel, and for us, soon to be fulfilled in these end times (cf. Romans 11:12; Romans 11:15; Romans 11:26).