Setting and Overview
The final three of Matthew’s “Seven Woes” serve as the conclusion to the chiastic pattern of the full set. As Jesus began by declaring that they have rejected Jesus, stemming from their misplaced zeal, stemming in turn from their failed application of Scripture, which in turn can be connected to a failure to understand the focus of God’s Word, he now concludes by working his way back out to show the result of that failure, and the punishment to which it inevitably leads.

Exposition
The fifth woe begins with the familiar identification of the Pharisees and experts in the law as hypocrites, a refrain that he will continue to the end and build on further in the sixth. He points out specifically that they clean the outside of dishes, a practice that Mark alluded to in Mark 7:4. While this practice was not specifically addressed in the Old Testament, the more general topic of ritual washing could be tied back to the commands for the priests to wash their hands when entering the tabernacle (Exodus 30:19) and for all to wash their hands after touching a bodily discharge (Leviticus 15:11.) The application to cups and dishes stems from a reference in Zechariah 14:20-21 to every pot becoming holy, and then this led to traditions of washing cups and dishes. The Shammaite, who were dominant at the time, believed that even the outside of the cups needed to be washed, and so Jesus points out the inconsistency of their attitude. That fervor did not translate to addressing what was inside them (Matthew 15:18-20) which was like cleaning a cup thoroughly only to fill with tainted water.
His sixth woe identifies them as whitewashed tombs. Tombs indeed were whitewashed in order to protect someone from accidentally stumbling across them and becoming ritually unclean (Numbers 19:16), but that probably isn’t the full meaning of the reference. The whitewash didn’t make the tombs beautiful, but the whitewashing also connected back to the practice of whitewashing walls to make them look more fortified than they were (Ezekiel 13:10-16.) Similarly, the tombs would often contain ornate monuments that were incongruent with the ugly remains inside. Jesus then combines a literal and figurative reference to point out that his subjects likewise try to cover up their ugly hearts with a façade of superficial righteousness.
Jesus concludes the woes with another mention of tombs. This time he references the practice of the time of building ornate memorials for the dead, including for those who had died long before (Acts 2:29.) Those who did so visibly were in effect identifying themselves as the spiritual successors of the prophets they were ostensibly honoring, but Jesus sees them being the spiritual successors of those who had killed the same prophets. They prove this identification by rejecting Jesus, to whom the prophets had been pointing. Therefore, the punishment that the contemporary leaders would pronounce on those who had killed the earlier prophets, is the punishment that they face themselves, as they are carrying forward their work to the appointed time of punishment (Genesis 15:6)

Examination and Application
Although Jesus is addressing those who are rejecting him, the warnings should nevertheless lead to self-examination for us as well. Do our lives point to sincere faith, or to masked self-indulgence? Do we truly mourn over our sin and repent (Matthew 5:3-4, James 4:8-9)? Do we cover up our sinful nature and worry about looking better to others, or do we humbly confess our sins to one another and look for edification and accountability (James 5:15-16)? Finally, are we willing, in love, to declare the eternal punishment that is in store for all who oppose Christ (I Thessalonians 2:14-16), punishment that we ourselves deserved (Ephesians 2:1-3), but from which we were rescued by the grace of God (Romans 3:21-26) which we are now called to share desperately with a world in need of saving (Romans 9:1-5.)