Matthew 23 is a prophetic judgment speech condemning the Pharisees and other Jewish religious leaders for their hypocrisy. This is not the first time Jesus speaks against the Pharisees. In Matthew 15:1-9 he dismisses their traditions of handwashing and in Matthew 16 he warns his disciples about the “the leaven of the Pharisees and Sadducees.” Now Jesus uses the word “woe” to draw attention to specific aspects of their hypocrisy. What does the word “woe” mean?
The word woe (οὐαί, הוֹי) is sometimes translated “alas” in English, giving it the idea of despair, or a sense of hopelessness. The word carries the connotation of mourning and is an onomatopoeia, a word that comes from a sound. Even today, people mourn in the Middle East with a whooping sound. Women at a funeral, for example, wail dramatically.
In this case, the word is drawn from the Old Testament Prophets. Both Isaiah 5:8-30 or Habakkuk 3 have a series of woe-statements pronouncing judgment. In Isaiah 6:5, the prophet sees the throne of God and says, “Woe is me!” because he has seen the holy God (and he expects to be destroyed as a result!) Other prophets use the word to announce doom on some people who are under God’s judgment. A woe is therefore something like a curse. In Matthew 23, Jesus makes a prophetic announcement that the Pharisees and other religious leaders are under a curse because of their hypocritical practices.
Lists of woe sayings are common in Jewish literature. Deuteronomy 28:15–19 has a series of four woes on those who do not obey the word of the Lord. There are three in in 1 Enoch 100:7–9 and five in 1 Enoch 96:4-8; 99:11-16, seven in 1 Enoch 94:6-7. Like Matthew 23, there are seven woes in 2 Enoch 52:1-14; 9 and eight in 1 Enoch 98:9-99:2. Here are a few examples from 1 Enoch:
1 Enoch 98.9 Woe unto you, fools, for you shall perish through your folly! You do not listen to the wise, and you shall not receive good things.
1 Enoch 98.11 Woe unto you obstinate of heart, who do evil and devour blood! From where (will you find) good things that you may eat, drink, and be satisfied?
1 Enoch 98.13 Woe unto you who rejoice in the suffering of the righteous ones! For no grave shall be dug for you.
In the Sermon on the Mount, Jesus gave a series of “blessed are” statements, these woes are the counterpart to those beatitudes. Luke has only four beatitudes, but they are mirrored by “four cursed are you” sayings in the next paragraph. Matthew begins Jesus’s public teaching with blessings and ends his public teaching with a series of curses. Maybe in a modern context, we want avoid the word woe, or worse, curse. If a beatitude is “happy are you when this is the case…” the woe-sayings are “unhappy are you when this is the case…”
Were all the Pharisees and religious leaders bad? Matthew 23 leaves the reader with that impression. He does not portray any of the religious leaders in a positive light. The Gospel of Luke more positive and in Acts the Pharisee Gamaliel defends the apostles. Later, Luke says there are many Pharisees who have accepted Jesus as Messiah (Acts 15:1-2), including rabbi Saul. In John, the pharisee Nicodemus talks with Jesus, defends him against accusations and helps bury Jesus. But Matthew is clear: the Pharisees are hypocrites who have rejected Jesus as the Messiah and they are to blame for judgment falling on Jerusalem (Matthew 24-25).
The Pharisees and scribes are made to be the representatives of all Jews. By condemning the Pharisees, Jesus is does not approve of Sadducees, the Essenes, or any other group. Other than Jesus’s followers, they are guilty of rejecting the Messiah.