What are the seven woes Jesus pronounced on the scribes and Pharisees in Matthew 23?

TL;DR:

Jesus pronounced seven woes condemning the hypocrisy of the scribes and Pharisees. He pronounced these woes because they were leading people astray and were misrepresenting God’s Word.

In Matthew 23, Jesus pronounced seven woes to the religious leaders of His day, pointing out ways they were being hypocritical. In the first, Jesus condemned them for leading others down the same path they were going—away from the Lord’s kingdom (Matthew 23:13). The second woe similarly convicts them of being missionaries who lead their converts to hell rather than to God’s kingdom (Matthew 23:15) The third woe pointed out how the leaders placed more value on the offered gifts and gold inside the temple than they placed on the presence and power of God "who dwells in it" (Matthew 23:16, 21). The fourth woe exposed their concern with minute details of tithing while ignoring “justice and mercy and faithfulness" (Matthew 23:23). The fifth and sixth woes expose the religious leaders' concern for the outward appearance of righteousness while ignoring the inward failings of "greed and self-indulgence" (Matthew 23:25) and "hypocrisy and lawlessness" (Matthew 23:28). In the final woe, Jesus revealed the emptiness of the religious leaders' claims that they wouldn’t have killed God’s prophets of old; their words rang hollow since they would call for Jesus’ death a few days later (Matthew 23:30; 27:1). Overall, Jesus shows in Matthew 23 that hypocrisy has no place in the lives of those who love God.

from the old testament

The Old Testament is filled with examples of God’s condemnation of the sinful priests who were not doing what God had called them to do. In Micah 3:11, God condemns these false spiritual leaders: “Its heads give judgment for a bribe; its priests teach for a price; its prophets practice divination for money; yet they lean on the LORD and say, ‘Is not the LORD in the midst of us? No disaster shall come upon us.’” Like the Pharisees during Jesus’ day, these prophets had a veneer of holiness but were spiritually dead inside.

from the new testament

In Matthew 23:13, Jesus shows that the Pharisees were leading others on the path they were going, which was away from the kingdom of God: “But woe to you, scribes and Pharisees, hypocrites! For you shut the kingdom of heaven in people's faces. For you neither enter yourselves nor allow those who would enter to go in.” Their actions were not only hurting themselves, but they were leading others to destruction.
Matthew 23:15 iterates the warning about the Pharisees leading others astray: “Woe to you, scribes and Pharisees, hypocrites! For you travel across sea and land to make a single proselyte, and when he becomes a proselyte, you make him twice as much a child of hell as yourselves.”
Matthew 23:16–17 demonstrates that the religious leaders of the time valued the material more than God Himself: “Woe to you, blind guides, who say, ‘If anyone swears by the temple, it is nothing, but if anyone swears by the gold of the temple, he is bound by his oath.’ You blind fools! For which is greater, the gold or the temple that has made the gold sacred?”
Matthew 23:23 points out the hypocrisy of the scribes and Pharisees in how particular they were about minute matters while overlooking spiritual matters: “Woe to you, scribes and Pharisees, hypocrites! For you tithe mint and dill and cumin, and have neglected the weightier matters of the law: justice and mercy and faithfulness. These you ought to have done, without neglecting the others.”
Jesus uses a metaphor in Matthew 23:25–26 to point out how “clean” the Pharisees looked outwardly but how dirty they were inwardly: “Woe to you, scribes and Pharisees, hypocrites! For you clean the outside of the cup and the plate, but inside they are full of greed and self-indulgence. You blind Pharisee! First clean the inside of the cup and the plate, that the outside also may be clean.”
In Matthew 23:27–28, Jesus presents another metaphor to communicate the religious leaders’ hypocrisy, pointing out that though they seemed spiritually alive outwardly, they were spiritually dead inwardly: “Woe to you, scribes and Pharisees, hypocrites! For you are like whitewashed tombs, which outwardly appear beautiful, but within are full of dead people's bones and all uncleanness. So you also outwardly appear righteous to others, but within you are full of hypocrisy and lawlessness.”
Finally, in Matthew 23:29–31 Jesus exposes the lie of the scribes’ and Pharisees’ claim that they wouldn’t have killed God’s prophets as their fathers did. These same people would soon be responsible for His death: “Woe to you, scribes and Pharisees, hypocrites! For you build the tombs of the prophets and decorate the monuments of the righteous, saying, ‘If we had lived in the days of our fathers, we would not have taken part with them in shedding the blood of the prophets.’ Thus you witness against yourselves that you are sons of those who murdered the prophets.”

implications for today

The seven woes that Jesus pronounces warn us how seriously He takes hypocrisy. Claiming to have moral standards to which one's own behavior does not conform is serious. Further, creating one’s own rules for living and holding them above God’s Word leads people astray and keeps people from knowing and coming to God. Jesus' condemnations and warnings to the scribes and Pharisees remind us to examine our motives and actions closely. We need to ask ourselves if we are truly pursuing justice, mercy, and faithfulness or if we are merely projecting an image of faith without the heart to back it up. Are we going through the motions of faith self-righteously, or are our actions motivated by love of God and others? To avoid spiritual blindness and becoming like the scribes and Pharisees, we should continually seek God to search our hearts, making sure our lives line up with His truth and the heart behind it. By focusing on our relationship with God rather than appearances, we can avoid the dangers of hypocrisy and point others to God by our lives.

understand

Jesus pronounced seven woes on the scribes and Pharisees for being hypocritical and leading people away from God.
Jesus pronounced seven woes on the scribes and Pharisees for prioritizing rituals and rules over justice and mercy.
Jesus pronounced seven woes on the scribes and Pharisees for appearing holy but neglecting inner purity.

reflect

Are there areas in your life where you’re more focused on appearances or rituals rather than true devotion to God?
How can you pursue loving God and loving others in your actions rather than getting caught up in doing things for their outward appearances?
How are you seeking to be formed by God’s Word and Spirit instead of by self-righteousness?

engage

In later manuscripts an eighth woe is inserted after the first that says the leaders were taking advantage of widows but making themselves appear pious by publicly praying extensive prayers; however, most Bibles now include this verse only as a footnote.
What are some ways that we as believers might unknowingly be prioritizing tradition over the true heart of God’s Word?
How can we support others to seek genuine, inward transformation instead of just maintaining a polished outward appearance?