Woe there: how did Jesus treat his enemies? (Matthew 23)

Warnings of a dangerous path, not wishes for disaster. That’s what Jesus meant by “Woe.”

If you think Jesus deserves a Nobel Peace Prize, you might be shocked by the way he addressed his enemies. Should we follow his example? This post helps you put his declarations of woe (Matthew 23) in context.

Jesus was approaching the capital to be recognized as king. That’s how the people called it: the son of David, coming in the name of the Lord to save his people (see on 21:9). But their joyful news sent shock waves through the powerful people of the city.

Initially it wasn’t the Roman Procurator who felt threatened. It was the leaders of his own people: the temple leaders (high priests), the leading Torah scholars (scribes), and the social engineers who controlled the community’s honour and shame (Pharisees). They were horrified by the gospel of this Galilean overturning their authority (21:12-17).

“Who do you think you are?” they challenged (21:23). Jesus gave them no ammunition. He told stories that painted their authority as a sham. “You only feign obedience to our Father” (21:28-32). “You’re the tenants who kill the son to keep the vineyard” (21:33-43). “You’re the guests who refuse the king’s call to honour his son” (22:1-14).

All their attempts to discredit him failed (22:15-40). A king greater than David was taking his seat in Jerusalem, expecting heaven to bring his enemies under his feet (22:41-46). That’s why Jesus confronted his enemies as he did: not as a military commander, but as a prophet.

Jesus did not march into the city with an army to force his enemies under his feet. He arrived as the king of peace, receiving the kingship in the name of their heavenly sovereign (21:1-8). His message was not Caesar’s, “Resist me, and I’ll kill you!” His was a prophet’s message, “It won’t go well for you if you resist what God decrees.”

Ideally, Israel’s kings spoke for the throne above theirs. Saul prophesied when God anointed him (1 Samuel 10:12). David did too (1 Samuel 16:13), speaking by the Spirit as Jesus called it (22:43).

When the kings weren’t listening to the Lord, he sent prophets to call them back to his authority. The word of the Lord through the prophets was a two-sided sword: “It won’t go well for you on the path you’ve taken (woe), so turn back to me and I’ll save you (blessing).” The prophets were saying that God enforces his Law: blessings for those who obey him, and woes for those who don’t (Deuteronomy 28). The prophets weren’t threatening the people. Okay, some did, but Jesus didn’t agree with them (Luke 9:54-55 compare 2 Kings 1:10-15).

When a sign says, “Stay back; unstable cliffs,” it isn’t a threat but a warning. Jesus used the word woe seven times in Matthew 23. He wasn’t wishing evil on anyone; he was warning of trouble ahead. The same word (ouai) in the next chapter is translated, how dreadful it will be. When Jesus spoke of woe for pregnant women and nursing mothers (24:19), he wasn’t condemning them or imprecating evil on them: he was empathizing with how horrid it would be when Rome invaded. It’s difficult for expectant mothers to run, for those with crying infants in their arms to hide.

That’s what Jesus meant by woe. It’s not revenge. It’s not a threat. It’s a warning to his enemies that they’ll find themselves on the wrong side of history if they murder the king God has given them. That’s the point the whole discourse is driving toward (23:29-39).

Matthew says God’s anointed had already silenced his enemies (22:34; 46). He would not use violence to unseat them. He would take his throne, while heaven deals with his enemies (22:44). His sevenfold woe is the prophetic announcement, “It will not go well for you if you resist what God has decreed.”

Jesus began his ministry by announcing his kingship as good news for the people who haven’t had a fair go (Matthew 5:3), for those who’ve been grieving their losses (5:4), for the people without power (5:5), for those who’ve never received the justice they sought (5:6). Now he announces the other side of that story: the gospel is disaster (woe) for those who act as if they have power over people. The true king exposes their power claims as mere role-playing (hypokritēs = play-acting: 23:13, 15, 23, 25, 27, 29).

Blessings for those who’ve been missing out, and woe for those in power. The Christ is confrontational because heaven has given him authority to sort out what’s wrong on earth.

Open Matthew 23.

What others are saying

Ceslas Spicq and James D. Ernest, Theological Lexicon of the New Testament (Peabody, MA: Hendrickson Publishers, 1994), 2:442:

Ouai is a transliteration of the Hebrew ʾôy, hôy, a sort of onomatopoeia, a cry of pain, terror, indignation, and sometimes threat, a declaration of misfortune and a complaint against a certain person or group, given one’s misery or privations.

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Author: Allen Browne

Seeking to understand Jesus in the terms he chose to describe himself: son of man (his identity), and kingdom of God (his mission). Riverview Church, Perth, Western Australia

2 thoughts on “Woe there: how did Jesus treat his enemies? (Matthew 23)”

  1. In Matthew 5:44, Jesus says “…love your enemies, bless those who curse you, do good to those who hate you.” In Colossians 4:6 Paul says “Let your speech always be with grace, seasoned with salt…”, yet seemingly Stephen the Martyr ignored those instructions in Acts 7:54 and Christ himself seemingly did likewise In Matthew 23. How are we to understand and reconcile that? I have been puzzled by this.

    Liked by 1 person

    1. Hi Brian. Great question.
      Based on the texts you mentioned, would you conclude that grace is not inconsistent with speaking out? Jesus, Paul, and Stephen were all outspoken at times.
      Who did they speak out against? It wasn’t the Roman government. It wasn’t the tax collectors and sinners in the community. They spoke out against leaders of God’s people, leaders who were misrepresenting God with their power claims.
      Refusing to confront abusive people in places of power in the church isn’t grace; it’s partnership in abuse.


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