Woe to You, Scribes and Pharisees, Hypocrites! (vv. 13-36)

Jesus next said eight times, “Woe to you, scribes and Pharisees, hypocrites!” (in verses 13, 14, 15, 16, 23, 25, 27, and 29). This series of “woes” have forever made the name “Pharisee” synonymous with “Hypocrite” in our Western culture.

How did Jesus say these words? Were they angry denunciations? Or were they sad commentary on the reality of their spiritual poverty? I believe the context indicates it was the latter. The Greek word used for woe is οὐαί pronounced oo-ah’ee. (It almost sounds like a plaintiff why? Thayer says it is “an interjection of grief or of denunciation.” Strong calls it “a primary exclamation of grief” while also recognizing its use as “woe.” So the word is capable of either angry denunciation or of a sad commentary.

The context, however, makes it clear that Jesus used it here as an expression of grief. Immediately after the eight “woe to you” statements, He said:

O Jerusalem, Jerusalem, the one who kills the prophets and stones those who are sent to her! How often I wanted to gather your children together as a hen gathers her chicks under her wings, but you were not willing! See! Your house is left to you desolate; for I say to you, you shall see Me no more till you say, “Blessed is He who comes in the name of the Lord!” – Matthew 23:37-39

What about the Pharisees caused grief to Jesus?

1. They neither entered the kingdom of heaven themselves nor allowed others to enter it. (v. 13)
2. They extorted widows’ property while making long, pretentious prayers. (v. 14)
3. They eagerly made proselytes only to make these even worse than they themselves were. (v. 15)
4. They were sophists in the rules they made about swearing – as a means of saying their oaths were not binding – much like children who make promises, but then say “I had my fingers crossed so it doesn’t count!” (vv. 16-22)
5. They majored in minors while neglecting the more important things. They were scrupulous in externals, but neglected the things that reflect the character of God. (vv. 23-24) Note: the next two “woes” continue this theme.
6. They cleaned the outside of the cup without washing the inside. (vv. 25-26)
7. They are beautiful sepulchers that are full of dead men’s bones. (vv. 27-28) The message is clear: a beautiful grave is still a grave “inhabited” by a dead person.
8. They piously said they would not have acted as their fathers had if they had been there – while all the time behaving exactly as their forefathers had done. (vv. 29-36)

In short, their behavior did not match their pious words. They did not practice what they preached, except as a means of making themselves look good to others.

While our doctrines today differ from those of the Pharisees, many times our behavior matches theirs exactly. That is why this passage is crucial for Christians today, especially for those who are leaders in the church.

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