In verses 4-22 Jesus answers the disciples' questions. The first part of Jesus’ answer has to do with many bad things that will happen but which are not in themselves signs of the end. He lists these in verses 4-14, then gives a particularly terrible example of such a bad thing in verses 15-22.
There are few things so fascinating as prophecy, or so problematic. Prophecy is fascinating because most people would like to know the future. Some would like to know it out of fear. They would like to be able to avoid life’s difficulties or tragedies. Some would like to know what is coming in order to plan for it successfully. If we could know what the stock market will do in the next few months or years, we could all become wealthy. Other people would like to know what is coming out of simple curiosity, to be on the inside track, as it were. Christian speculations about the future are often in this category. In the secular world horoscopes, fortune tellers, seances, tarot cards, and the popularity of cult figures like Jeane Dixon show how fascinated most people are with what is coming
Today we will explore the final two woes—for wickedness within and for the murder of God’s prophets.
6. For wickedness within (vv. 27-28). The fifth woe leads naturally to the sixth, for having spoken of the dirty insides of their lives, like the contaminated inside of an outwardly polished cup, Jesus added the well-known illustration of whitewashed tombs containing "dead men's bones and everything unclean,” a euphemism for decaying human matter.
We have been discussing the seven woes Jesus spoke to the Pharisees. The third is for trivializing religion. Jesus called people who handle truth in this useless and corrupting way "blind guides," meaning that they cannot see spiritual issues clearly and therefore not only lead others wrongly but fall into a pit themselves (Matthew 15:14). Are we to suppose that there is nothing of this in today's religious circles? I suggest that this happens whenever teachers make delicate distinctions about things the Bible teaches, arguing, "This may be sin, but this closely-related type of misconduct is not” or “Jesus may be saying this, but again he may be saying something quite different,” and fail to take the Bible’s statements at face value and insist not only that truth is truth but that it is always truth and is binding on everyone.
In the Sermon on the Mount Jesus had pronounced multiple blessings on the godly. Here, in the later half of Matthew 23 he pronounces seven "woes” on the wicked. This follows an established Old Testament pattern, seen for example in Isaiah 5:8-23, where there are six woes, and in Habakkuk 2:6-20, where there are five. There is something similar in Revelation 19:9-20. A woe is a lament, cry or judgment concerning the final end for evil people.
