Jesus Knows What He is Riding Into

Text: Matthew 21:1-11

“Blessed is the King who comes in the name of the Lord! Peace in heaven and glory in the highest!” —Luke 19:38

Have you ever been guilty of misinterpreting a situation? How many times have you said to yourself: If only I had known then what I know now? The old saying “hindsight is always 20/20” certainly has relevance in our lives, as it did for the disciples when Jesus came riding into Jerusalem during his triumphal entry (John 12:16).

Palm Sunday is the day we observe that triumphal entry. In the Christian tradition, Palm Sunday serves as a preparation of one’s heart for the agony of Jesus’ passion and the joy of His resurrection. It’s the beginning of Passion Week (Holy Week)—that fateful week in which Jesus entered the holy city to face his cross. Here our Lord would drink the cup of suffering. By the end of the week, he would be betrayed, arrested, tortured, and crucified. His followers would be confused, disoriented, and scattered. But not this day…

This day, riding on a donkey, Jesus entered the city and is greeted by ecstatic crowds waving palm branches in celebratory honor. The adulation! The applause! The political rallying! They loved him on this day but were suddenly ready to kill him by Thursday! How fickle this crowd would prove to be. Within a few days, many of those same voices shouting “Hosanna” would turn to raging howls of “Crucify him! Crucify him!” (Luke 23:21)

Momentarily, while the crowds are enamored with Jesus, the disciples are probably feeling pretty good. It seems like everything is falling into place for a new earthly kingdom to emerge. Jerusalem is welcoming their king. The people are anticipating a Messiah who will rescue them politically and free them from societal oppression—to overthrow the Roman Empire and reestablish Israel’s power in the world. But God is up to something so much bigger.

Jesus is about to turn the whole system upside down.

He rides in on a lowly donkey. Now a donkey is hardly the stuff of a royal motorcade. Yet some 500 years prior to Jesus’ arrival in Jerusalem, the prophet Zechariah had already prophesied this event would take place precisely in this fashion (Zechariah 9:9), adding to over 300 other Old Testament prophecies Jesus fulfilled.

In the ancient Biblical world, a leader rode on a horse to declare war, but on a donkey to signify peace. Jesus didn’t come with violence. He didn’t come with bloodshed. He didn’t come with hostility. He came in humility and servitude—to give his life as a ransom for many (Mark 10:45). He didn’t take life; he gave up his own life to save the world.

Greater love has no one than this, that someone lay down his life for his friends. —John 15:13

Once the crowds saw no more political capital in Jesus, they turned on him overnight. But Jesus knew what he was riding into. He came to suffer and die for the sins of the world. By triumphing over the grave, the risen King of glory has established a kingdom that is not of this world—but a Kingdom that has conquered this world!

Sometimes God’s plans don’t make sense in the moment. His infinite ways can never be constrained by our finite understanding—though He can certainly be trusted.

Jesus knows full well what he is riding into in your life. He knows the hurt, the loneliness, the grief, the betrayal, the anger, the doubt, the despair, the exhaustion, the weariness, and the constant struggle. He knows all the madness. Yet your King lives, beloved—and he will indeed triumph over every last bit of it. Think about that as you seek to abide in Him this week.


King Jesus, I worship you! You didn’t enter your holy city on the back of an intimidating warhorse, but humbly on a lowly donkey. You knew what you were riding into—the hostility of a lethal multitude—yet you came in peace. You died for my sin; you conquered the grave and disarmed the power of death that holy week. You laid down your life to save mine. You are worthy of my praise! I will sing of your goodness and continue to declare your deeds to the next generation. Your kingdom come! Your will be done, here on earth as it is in heaven. In Your name, Amen.

Questions for Reflection and/or Family Discussion:

  1. Can you share a time you couldn’t figure out what God was doing in your life, only to understand more clearly later?
  2. What strikes you most about the imagery of Jesus riding in on a donkey?
  3. If Jesus were to ride into Washington, D.C., on a donkey today, what do you think the headlines would read?
  4. What kind of reaction do you think the religious leaders had during Christ’s triumphal entry? (John 12:19) Why do you imagine they were so threatened by Jesus?
  5. Jesus knows full well what he is riding into in your life, and he’s not the least bit intimidated by any of the drama. How can you find rest in that this week?

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