Matthew 21
1 As they approached Jerusalem and came to Bethphage on the Mount of Olives, Jesus sent two disciples, 2 saying to them, “Go to the village ahead of you, and at once you will find a donkey tied there, with her colt by her. Untie them and bring them to me. 3 If anyone says anything to you, say that the Lord needs them, and he will send them right away.”
4 This took place to fulfill what was spoken through the prophet:
5 “Say to Daughter Zion,
‘See, your king comes to you,
gentle and riding on a donkey,
and on a colt, the foal of a donkey.’”
6 The disciples went and did as Jesus had instructed them. 7 They brought the donkey and the colt and placed their cloaks on them for Jesus to sit on. 8 A very large crowd spread their cloaks on the road, while others cut branches from the trees and spread them on the road. 9 The crowds that went ahead of him and those that followed shouted,
“Hosanna to the Son of David!”
“Blessed is he who comes in the name of the Lord!”
“Hosanna in the highest heaven!”
10 When Jesus entered Jerusalem, the whole city was stirred and asked, “Who is this?”
11 The crowds answered, “This is Jesus, the prophet from Nazareth in Galilee.”
“Everything in Christ astonishes me. His spirit overawes me, and his will confounds me. Between him and whoever else in the world, there is no possible term of comparison. He is truly a being by himself… I search in vain in history to find the similar to Jesus Christ, or anything which can approach the gospel. Neither history, nor humanity, nor the ages, nor nature, offer me anything with which I am able to compare it or to explain it. Here everything is extraordinary”
-Napoleon (Philip Yancey’s - The Jesus I Never Knew)
Let’s talk about the details of this story…
1) Timing - Passover
Jesus enters into this moment of great religious expectation.
GOD COMES WHERE HE IS WANTED.
Habakkuk 3:2-3
Lord, I have heard of your fame;
I stand in awe of your deeds, Lord.
Repeat them in our day,
in our time make them known;
in wrath remember mercy.
Prayer for Holy Week - Live expectantly for God
2) Place - Bethpage on the Mount of Olives.
Isaiah 55:8-9
8 “For my thoughts are not your thoughts,
neither are your ways my ways,”
declares the Lord.
9 “As the heavens are higher than the earth,
so are my ways higher than your ways
and my thoughts than your thoughts.
God shows up differently than you might expect.
Prayer for Holy Week - Live openly to God
3) Parade - Triumphal Entry
The crowd is receiving Jesus as king.
-vs. 5 - donkey - fulfillment of prophecy
-They spread cloaks in front of him
2 Kings 9:13 - They quickly took their cloaks and spread them under him on the bare steps. Then they blew the trumpet and shouted, “Jehu is king!”
-They cut down palm branches and waived them
Maccabeus Revolt
-The crowd shouts out Hosanna! vs. 9 - sing royal hymns to him - Hosanna - “save now” salvation is here. We need saving!
John 18:36
Jesus said, “My kingdom is not of this world. If it were, my servants would fight to prevent my arrest by the Jewish leaders. But now my kingdom is from another place.”
Prayer for Holy Week - Live differently with God
Palm Sunday declares Jesus is King, the Messiah, the savior. But his rule is not of this world.
Palms Sunday declares Jesus is a King that sacrifices for us so we may have life.
We don’t follow and swear our allegiance out of fear, but out of a response to love.
Jesus is the king we desperately need, not the king we selfishly want.
Jesus enters our hearts the same way. He doesn’t ravish, he can only woo. But he invites us into this new kingdom where he reigns. Do you accept this?
Communion
Small Group Questions
Opening Icebreaker
What’s one memorable parade or public celebration you’ve attended? What made it so special?
Read Matthew 21:1–11 Together
1. Timing – Jesus Comes Where He Is Wanted
“Jesus enters into this moment of great religious expectation.”
Why do you think Jesus chose to enter Jerusalem during Passover?
Have you ever experienced a time when God showed up powerfully because you were truly expectant or open to Him?
Prayer Focus: What would it look like for you to live expectantly for God this Holy Week?
2. Place – God Shows Up Differently Than Expected
“God’s ways are higher… God often shows up in surprising ways.”
The Mount of Olives was full of prophetic meaning. Why do you think Jesus started there?
When has God showed up in your life in a way that surprised you or didn’t make sense at the time?
Prayer Focus: Where might God be inviting you to live more openly to Him this week, even if it doesn’t look how you imagined?
3. Parade – The King Who Saves
“Hosanna! Blessed is He who comes in the name of the Lord!”
The people shouted “Hosanna” (meaning “save now”) — how do you think they were hoping Jesus would save them?
Jesus’ kingdom is not of this world (John 18:36). What are some differences between Jesus’ kingdom and the kingdoms or values of this world?
What does it mean to live under Jesus’ rule as King? How does that challenge or change your daily life?
Prayer Focus: How can you live differently with God this week as you follow the Servant King?
Closing Prayer
Use Habakkuk 3:2 as a guide:
“Lord, we have heard of your fame; we stand in awe of your deeds. Repeat them in our day…”
Spend time praying together, asking God to make His presence known in fresh ways this Holy Week. Pray for hearts that are expectant, open, and surrendered to the true King.