Unlikely King

This past weekend at Eastbrook, we began a new preaching series entitled “Scandalous Jesus,” that parallels our journey of Lent. This week, I turned our attention to two episodes that set up the entire series and Jesus’ time in Jerusalem. The first was Jesus’ third prediction of His coming suffering in Jerusalem (Matthew 20:17-19) and the second relates Jesus’ triumphal entry into Jerusalem (Matthew 21:1-11). I explore these texts and also reflect on how we can see them in a fresh way once again.

This message is from the ninth part of our longer journey through the Gospel of Matthew, which includes “Family Tree,” “Power in Preparation,” “Becoming Real,” “The Messiah’s Mission,” “Stories of the Kingdom,” “Who Do You Say I Am?“, “‘Tis the Reason,” and “Jesus Said What?!

You can find the message video and outline below. You can also view the entire series here. Join us for weekend worship in-person or remotely via Eastbrook at Home.


“Now Jesus was going up to Jerusalem. On the way, he took the Twelve aside and said to them, ‘We are going up to Jerusalem, and the Son of Man will be delivered over to the chief priests and the teachers of the law. They will condemn him to death.’” (Matthew 20:17-18)

Jesus’ Shocking Predictions of Messianic Suffering

First prediction (Matthew 16:21) – in Caesarea Philippi

Second prediction (Matthew 17:22-23) – in Galilee on the way to Jerusalem

Third prediction (Matthew 20:17-19) – nearing Jerusalem

The Shocking Promise of Suffering and Hope of Resurrection (20:18-19)

Handed over – entrusted – betrayed; hints at the role of Judas

Condemned to death by the chief priests and teachers of the law

Mocked, flogged, and crucified by the Gentiles

Raised to life on the third day 

The Shocking Entry to Jerusalem (21:1-11)

Mount of Olives and the end of the age (Zechariah 14)

The contrast of Galilee and Jerusalem

The Messianic King arrives meekly, bringing true peace (Zechariah 9:9-10)

The secret is revealed and the crowd acclaims Jesus

The moment of confrontation has come

Seeing Jesus with Fresh Eyes

The Biblical journey

The Lenten community journey


Dig Deeper

This week dig deeper in one or more of the following ways:

  • Memorize Matthew 20:18-19 or 21:9
  • Draw, ink, or paint Matthew 21:1-11 as a basis for prayer. Take time to talk with God as you depict the scene in your own way. What is God speaking to you through this account of the triumphal entry of Jesus into Jerusalem? 
  • Consider listening to the Bible Project podcast on Matthew 21, “Jesus, Prophet and Provocateur”

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