Key Verse: Matthew 23:11. Be a servant leader.
Personal Application: Strive for servanthood in your leadership, not the negative example here.
Outline: After three parables of rejection of the King (21) and three encounters of rejection with the King (22) followed by the King’s question about David’s Lord unanswered (22:36-41), the Lord Jesus now pronounces a fearful judgment on these men. This chapter begins Jesus fifth of five discourses in Matthew (chap. 23-25). His first discourse begins with blessings on the meek (5:1-12). This one begins with woes on the religious elite (chap. 23). Just as eight beatitudes, or blessings, we now see eight woes or judgments. Here in the Temple as in a court of law, the King prosecutes and condemns them for rejecting His Kingdom. We see the wrathful Jesus, but we also see the tender Jesus who weeps over the city (23:37-39).
The King addresses the Crowd in the Temple (Matthew 23:1-12)
Moses’ seat (23:2) – stone seat in synagogue where teacher of law sat to make authoritative statements in a dispute or giving instruction.
Jesus’ sarcasm (23:2-4) – Jesus is not affirming their right to adjudicate but is being ironic, intending the opposite of what he says.
Leaders must live what they teach (23:1-4)
Leaders must not seek honor for themselves (23:5)
Leaders should not expect special treatment (23:6)
Leaders should not seek titles (23:7-11)
Jesus encourages his listeners to be servant leaders, not hierarchical leaders who are corrupted by power.
The King charges the teachers with Woes (Matthew 23:13-32)
Hypocrites (23:13, 15, 23, 25, 27, 29) – the word is used for actors in a play. In Greek plays the masks were exaggerated. Here Jesus uses it to portray people who act with calculation intended to impress others (Matthew 6:1-3), focus on externals and ignore central heart issues (15:1-21), and use spiritual talk to hide corruption (22:18-22).
1. False leadership, shutting the door to the Kingdom and not allowing entrance (23:13).
2. Cloaking their own unrighteousness in religious forms and professions (23:14).
3. Zeal to proselytize but not for God’s glory – simply human ambition to get more followers (23:15).
4. Duplicity and deceitfulness in interpreting the Scripture (23:16).
5. Empty ceremonialism which questions minutia while omitting important things like justice, mercy, and faithfulness (23:23)
6. Image-conscious formalists who look good on the outside but hearts full of “greed and self-indulgence” (23:25).
7. Dead hearts like whitewashed tombs beautiful on the outside but inside filthy and full of dead bones (23:27).
8. Sentimental hypocrisy of decorating graves of prophets their ancestors killed while they plot to kill the Son of David (23:29-30).
The King Issues Royal Judgment (Matthew 23:33-36)
Zechariah (2 Chronicles 24:20-22)
The King Weeps over Jerusalem (Matthew 23:37-39)
While angry at these misleaders, Jesus weeps with compassion over them. Here as “I” he is claiming clearly to be God.
There will come a day when Jerusalem will weep over the King (Zechariah 12). Jerusalem will know peace only when Jesus is acknowledged as “He who comes in the name of the Lord.” Foreshadowing of Matthew 24; Deuteronomy 30:1-10
 Keener, Matthew, (IVP), 331-42.
 Simpson, The Christ in the Bible Commentary, 4:122-3.