“A Road Paved with Expectations” – Fr. Pete's Sermon for Palm/Passion Sunday (Witnesses Along the Way series), March 29, 2026

​Matthew 21:1-11

I live in Jerusalem, just inside a city gate. And that matters during Passover week, because everything comes through that gate—pilgrims, merchants, rumors, and sometimes trouble.
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By the time the festival begins, Jerusalem swells beyond itself. The streets fill with accents from Galilee and Judea, travelers sleeping wherever they can find space. Roman soldiers double their patrols. You can’t gather thousands of people to celebrate their deliverance from one empire, Egypt, without making the current empire, Rome, nervous. 

So when the shouting began that morning, I stepped outside to look. At first it sounded like any other surge of pilgrims entering the city—children laughing, people calling to one another, animals shuffling along the road. But then a single word began rising above the noise, over and over, until it rolled down the street like thunder:

Hosanna. Save us!

Now that word carries some history with it. Every child in Israel knows it. Every pilgrim sings it in the Psalms while approaching the Temple gates. But when people shout it in the streets like that, it means something more.

I pushed my way closer to the road. Branches were being torn from nearby trees—palms, mostly—and waved above the crowd. Cloaks were coming off shoulders and being spread across the dusty road. It looked less like a procession and more like the beginning of a festival.

“Who is it?” someone near me asked.

“The prophet,” another answered. “The one from Galilee.” Others added their own explanations: the healer, the teacher, the one who had raised the dead.

And then I saw him. At first just the top of his head above the crowd, the slow movement of people stepping aside. Gradually the road opened enough that I could see him clearly.

He was riding a donkey, a young colt, stepping carefully through the cloaks and branches people had thrown onto the road.

I remember feeling a strange mixture of excitement and confusion, because this is not how kings enter cities—and on a donkey!

Oh, I’ve seen Roman officials arrive before. When they come, soldiers clear the road first. Trumpets sound. Horses stamp the ground. Power makes itself obvious. This man—Jesus, they called him—entered quietly, almost gently, as though he did not want to scare away the very people shouting his name.

But the crowd did not quiet. If anything, the noise grew louder.

“Hosanna to the Son of David!”
“Blessed is the one who comes in the name of the Lord!”

They were singing the Psalms—the ancient songs we always sing when approaching the Temple gates. Words about salvation. Words about the day God would finally set things right. And suddenly those words felt less like a memory and more like a possibility.

I will admit something: I shouted too. It is hard not to be swept up into hope when hope moves through a crowd like that. When thousands of voices cry Hosanna, it begins to feel as though history itself might finally be turning.

But even as I waved a branch with the others, something about the scene unsettled me. Because I had seen men claim to be deliverers before. They gather followers, whisper plans, and stir the anger already simmering among the people. And Rome crushes them every time.

This man did none of that. He didn’t shout instructions. He did not raise his voice. He simply rode forward, looking out over the crowd with a calm I could not quite understand.

For a moment he passed close enough that our eyes met. And I had the strangest feeling—not that he was taking in our praise, but that he was already carrying something heavier.

Some of the religious leaders had come out to watch. I saw them standing at the edge of the crowd, whispering among themselves. One of them muttered, “Do you hear what they’re saying?”

Yes! We all heard it. Hosanna. Save us!  But that word is more dangerous than it sounds. Because when people shout Save us, they are usually imagining exactly how they want to be saved.

Save us from Rome. Save us from taxes and soldiers. Save us from humiliation. Save us from all this waiting for God to act, waiting for God to answer our prayers.

But what if God answers differently than we expect?

The procession moved deeper into the city. Cloaks covered the road like a patchwork carpet. Children ran ahead of the donkey, laughing and shouting the same ancient words: “Hosanna in the highest!”

And I found myself wondering something I had never wondered before: what kind of king chooses to arrive like this? Not with force. Not with fear. But with a humility that almost looked like weakness.

When the crowd moved further into the city, I stayed behind a moment. Branches people had been waving were beginning to droop in the morning heat. The road was being cleared, started looking ordinary again—just dust and stones.

Yet something had shifted. All day people kept asking the same question:

“Who is this?” I was asking it too!
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Some answered confidently: “This is the prophet Jesus from Nazareth in Galilee.” Others said more quietly, “The Messiah.” Still others shook their heads and said, “Trouble.” I did not know which answer was right.

All I knew was that this man had entered our city in a way no king ever had. He
accepted our praise, but he did not command it. He received our hopes, but he did not
promise to fulfill them the way we imagined.

Looking back now, I wonder if that road we covered with branches and cloaks was more than a welcome. Perhaps it was the beginning of something we could not yet see.

Because this king did not come to seize power. He came to reveal something far less expected. The crowd wanted a moment, they wanted a king. But he was beginning a journey—a journey that would move from cheers to silence, from palms to a cross, from hope shouted aloud to love poured out completely.

This day feels like a celebration, and it is. But it is also the threshold into the rest of the story.

Because once you have shouted Hosanna to a king like this, the question that follows is not only whether he will save us.

The question is whether we will follow him
wherever this road leads next….