This chapter records the final confrontation between Jesus and the Jewish religious leaders before His journey to the cross. Jesus again exposes the hypocrisy that has permeated throughout the nation's leadership and pronounces eight of the most thrilling oracles of woe that are found in the gospel account according to Matthew.
At the core of the problem was not their pursuit of religion. The problem centered on their internal heart posture. Their religion centered on themselves instead of on God. They burdened others with rules they were unwilling to carry, with great eagerness they sought recognition from men, and they obsessed over outward appearances. And all of this was done while neglecting the weightier matters of the law: justice, mercy, and faithfulness.
It's no wonder Jesus compared them to whitewashed tombs. They presented beautifully, but inside they were filthy. The external piety masked the hard hearts that were full of hypocrisy and lawlessness.
And these descriptions aren't designed to narrow our focus on only those who lived opposed to the ways of God 2,000 years ago. These woes we hear out of the mouth of Jesus should cause us all to examine ourselves. What a trap it is to read scripture and apply it to someone else or look down at the "villain" in the story. After all, who doesn't enjoy recognition? Who doesn't have blind spots? Jesus' words should lead us past the description of the Pharisees and into our own hearts. When we read this section of sacred scripture, David's words should echo in our heart, when the Psalmist cried out to God, "Search me, O God, and know my hear; try me and know my anxious thoughts; and see if there be any hurtful way in me, and lead me in the everlasting way." (Psalm 139:23-24).
The reason we should be ever so vigilant with our examination of our soul is given to us at the end of this chapter. Jesus ends his discussion with Israel's leadership with one of Scriptures most heartbreaking laments. "Jerusalem, Jerusalem, who kills the prophets and stones those who are sent to her! How often I wanted to gather your children together, the way a hen gathers her chicks under her wings, and you were unwilling. Behold, your house is being left to you desolate!" (v. 37-38). Their rejection, born out of the hard hearts, would bring devastating judgment, fulfilled in the destruction of Jerusalem in AD 70.
God desires a pure heart and a settled conscience. We should daily humble ourselves before our maker, examine our hearts, and let genuine righteousness flow from within.