The Journey to Jerusalem: A Palm Sunday Sermon
St. John tells us that five days before Jesus entered Jerusalem, he found a young donkey and, seated upon it, entered the Holy City. As he rode in, a crowd gathered as if welcoming a king into his royal palace. They grabbed branches from palm trees and began to shout:
Hosanna!
Gathered here today as Christians 2,000 years later, we relive this excitement. We become part of that crowd. We, too, have grabbed our palm branches and will join in the procession, hoping to welcome Jesus as the king of Jerusalem.
We get caught up in the celebration, forgetting what lies ahead. We forget that Holy Friday is just around the corner. We, like the disciples, don’t quite grasp what all this means. And yet we rejoice when Jesus says, “Fear not, daughter of Zion; behold, your king is coming, seated on the foal of a donkey.” And, all the louder, we shout:
Hosanna!
But something isn’t right. This king rides not on a war horse but on a humble donkey. The crowd expects a conquering hero, yet Jesus speaks of his coming death. We’re caught in a paradox—celebrating a victory while heading toward what appears to be defeat.
Let’s rewind. Today’s story actually begins in Bethany, the day before Palm Sunday. It starts with joy—Jesus has just raised Lazarus from the dead. A miracle! With such a beginning, what could go wrong?
Mary approaches with a jar of expensive perfume. She anoints Jesus’s feet and wipes them with her hair—a beautiful gesture of devotion. This is a sign that the Holy Spirit is with Jesus. Oil and the Spirit are connected. When chrism oil is used at our baptism, it’s a “seal of the gift of the Holy Spirit.” With this anointing, we are reminded of Christ’s anointing at his baptism—that this is God’s “Son, the beloved, in whom he is well pleased.”
And, so, we want to shout:
Hosanna!
But then Judas speaks up: “Why wasn’t this perfume sold and the money given to the poor?” On the surface, his question seems reasonable. Shouldn’t a king who cares for his people prioritize the poor over such extravagance?
Jesus’s response is perplexing: “Leave her alone. She bought it so that she might keep it for the day of my burial.”
Burial? This is supposed to be a coronation! The crowd wants a king who will overthrow Roman oppression, not one who speaks of dying. The disciples themselves cannot comprehend what’s happening. The equilibrium is thoroughly upset. With such confusion, how can we shout:
Hosanna!?
In every journey story, there’s an adversary. At the beginning of Jesus’s ministry, it was Satan who tested him in the desert. Here, it’s not just Judas who will betray him, but the very city of Jerusalem itself.
We often think of Jerusalem as the Holy City, but here it functions much differently. Jerusalem was the city of kings who turned away from God to worship idols. Leaders who didn’t care for the poor, the widowed, or the orphaned—the most vulnerable of society. Jerusalem represented a leadership that ended in disaster and exile.
In Jesus’s time, it continued to be a city that failed to demonstrate God’s love and mercy. It failed to be the light in the darkness. For this reason, Jesus had harsh things to say about Jerusalem and its temple.
This journey on Palm Sunday isn’t into a Holy City, but into the belly of the whale—into the chaos of destruction to confront corrupt powers, including Death. Jesus is entering enemy territory to find victory.
The clue to resolution emerges: Perhaps kingship isn’t what we thought it was. Perhaps salvation doesn’t come through military might or political power but through sacrifice. Perhaps, it’s for a different sort of kind that we shout:
Hosanna!
The way Jesus becomes king is through the cross. Jesus knew this, even as the disciples and the crowd misunderstood. This is why Mary’s anointing was for “the day of his burial.” This journey isn’t about taking a throne—it’s about mounting a cross.
Jerusalem isn’t just a physical place but represents Death and everything that stands against God’s kingdom. It’s the embodiment of our brokenness, our sin, our rebellion against God. And Jesus rides straight into it.
This isn’t just a parade of people with palm branches. It’s the story of how God confronts true evil in the world. Jesus doesn’t avoid Jerusalem’s corruption—he faces it head-on. He doesn’t overthrow it with violence but transforms it through sacrificial love.
The Gospel truth is revealed: God’s victory comes not through domination but through self-giving love. The king we welcome is one who serves, who kneels, who washes feet, who gives his life. This is why, with a renewed understanding, we can shout:
Hosanna!
As baptized Christians, we are called to join Christ on this same journey. In baptism, we are united to Christ in his death, and when we come up out of the waters, we are united to Christ in his resurrection. This isn’t just a ritual—it’s a roadmap for our own spiritual journeys.
We too are anointed in chrismation, “sealed with the gift of the Holy Spirit.” The Spirit lives in us, helping us on the way. But each of us is still called to journey to our own Jerusalem, into the belly of our own whale.
For each of us, the enemy presents itself differently. It may be addiction or anger, pride or control, depression or jealousy, gluttony or gossip. All our demons are different.
But we are called to confront that enemy, confront our passions. This is our spiritual journey, our path to Jerusalem. For each of us, it’s a lifelong journey. And yes, in the end, we may feel crucified before we can shout:
Hosanna!
Even if our enemy does its worst, even if our struggle ends in what looks like defeat, it does not matter. This is the story of Lazarus and Palm Sunday. This is the story of Good Friday. This is the story of Resurrection Sunday.
Only when we struggle and voluntarily journey to Jerusalem with Christ, confront our enemy, and let it do its worst to us, can we be transformed and reborn.
When we journey to Jerusalem and unite ourselves to Christ, the tomb becomes a womb, and we can eternally shout:
Hosanna!
Amen!