The Entry: The King We Didn’t Expect

Good morning.

If we haven’t met before, my name is Matt. I’m one of the pastors here. And I’m really glad you’re here today.

Over the next few weeks as we move toward Easter, we’re going to slow down and walk through the final days of Jesus’ life.

We’re going to take it slowly, one moment at a time, because everything about the Christian faith ultimately hinges on what happened during that week.

Today we begin with the moment Jesus enters Jerusalem.

Next Sunday we’ll look at the cross.

And then on Easter Sunday we’ll come to the resurrection itself.

Now if you’re someone who pays attention to the church calendar, you might notice that we’re doing something slightly unusual.

The story we’re beginning with today is what Christians traditionally call Palm Sunday — the moment when Jesus enters Jerusalem and the crowds welcome him as king.

But Palm Sunday is… next week.

So if you’re wondering why we’re starting there a week early, the answer is simply that this story deserves more than a few minutes of attention before we rush toward the cross.

It’s one of those moments in the Gospels that feels celebratory on the surface but becomes much more complicated the longer you sit with it.

Because at first glance, it looks like the beginning of a victory parade.

Crowds gather along the road.
Palm branches are waved.
Cloaks are spread on the ground.
People shout words of praise and hope as Jesus approaches the city.

It feels like the moment when everything is finally about to change.

And if you think about it, human beings have always been drawn to moments like that — moments when it seems like history itself might be turning.

You see it in politics when a new leader arrives and people begin imagining the future will finally look different.

You see it in technology when someone announces a breakthrough and suddenly everyone believes the world is about to enter a new era.

You see it in sports when a city gathers for a championship parade and for a few hours everyone believes this is the beginning of something great.

Crowds have a remarkable ability to recognize — or at least to believe they’re recognizing — the turning points of history.

And that’s the atmosphere surrounding Jesus as he approaches Jerusalem.

But to understand what’s happening in this moment, we have to step back and picture the city itself.

Jerusalem during Passover week would have been unlike the Jerusalem people experienced the rest of the year.

Historians estimate that the population of the city could swell dramatically during the festival as pilgrims traveled from across the region to celebrate Israel’s great story of deliverance.

Passover was the holiday when Jewish people remembered how God had rescued their ancestors from slavery in Egypt. It was the annual retelling of the moment when God had stepped into history and set his people free.

Which meant that every Passover carried with it a quiet question that lingered in the background: If God delivered us once… might he do it again?

And by the first century that question had become very personal for the people of Israel, because they were once again living under foreign rule.

Roman soldiers occupied their cities.
Roman taxes burdened their families.
Roman authority hung over their political and religious life.

Which meant that when people gathered in Jerusalem for Passover, they weren’t only remembering the past.

They were hoping for the future.

They were hoping that one day God would send a king.

The Messiah.

A descendant of David who would restore Israel, defeat oppression, and establish God’s kingdom in a visible and powerful way.

So imagine the city that week.

Thousands of pilgrims streaming into Jerusalem.

Religious leaders watching events carefully.

Roman soldiers stationed throughout the city to keep order.

And rumors spreading about a rabbi from Galilee who had been doing remarkable things.

People were talking about him everywhere.

Some said he had healed the sick.
Others said he had opened the eyes of the blind.
There were stories about him feeding thousands of people with only a few loaves of bread.
And recently — according to the Gospel of John — he had even raised a man named Lazarus from the dead just a few miles away in Bethany.

At that point you can imagine the conversations happening in the crowd.

“Maybe this is the one.”

“Maybe this is the Messiah.”

Then one day word begins spreading that Jesus is approaching Jerusalem.

People start gathering along the road leading toward the city.

Some begin cutting palm branches from the trees. Others take off their cloaks and spread them along the path in front of him.

And suddenly the crowd begins shouting words that come straight from the Psalms:
“Hosanna to the Son of David! Blessed is he who comes in the name of the Lord!”

And in that moment it must have felt as though history itself might be turning.

But as Matthew tells the story, something becomes clear very quickly.

The crowd was welcoming a king. They just didn’t yet understand what kind of king he was.

And if we’re honest, that tension isn’t only found in the story of Jesus entering Jerusalem. It’s something people still wrestle with today.

Many people are drawn to Jesus.
Many admire him.
Many appreciate parts of what he taught.

But the deeper question underneath all of that is still the same one the people in Jerusalem were facing that day.

What kind of king is this?

Let’s look at how Matthew actually tells the story.

If you have a Bible, turn with me to Matthew chapter 21. I want to read the account the way Matthew presents it, because the details matter.

As they approached Jerusalem and came to Bethphage on the Mount of Olives,

One small geographical detail that Matthew includes is easy to miss if you’re not familiar with the landscape around Jerusalem.

He tells us Jesus approaches the city from the Mount of Olives.

Now that might sound like a simple travel note, but to people in the first century it would have meant something more.

The prophet Zechariah had written that when God finally acted to deliver his people, the Lord would stand on the Mount of Olives overlooking Jerusalem.

So when Jesus approaches the city from that direction, people who knew the Scriptures would immediately recognize the symbolism.

It would feel as though the story Israel had been waiting for might finally be unfolding.

Jesus sent two disciples, 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. If anyone says anything to you, say that the Lord needs them, and he will send them right away.”

This took place to fulfill what was spoken through the prophet:

“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.’”

The disciples went and did as Jesus had instructed them. They brought the donkey and the colt and placed their cloaks on them for Jesus to sit on. A very large crowd spread their cloaks on the road, while others cut branches from the trees and spread them on the road.

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!”

When Jesus entered Jerusalem, the whole city was stirred and asked, “Who is this?”

The crowds answered, “This is Jesus, the prophet from Nazareth in Galilee.” (Matthew 21:1-11)

Now if you picture what Matthew just described, it really does look like the beginning of a royal procession.

People are gathering along the road.
Cloaks are being spread on the ground.
Palm branches are being cut and waved.
The crowd begins shouting, “Hosanna to the Son of David! Blessed is he who comes in the name of the Lord!”

Now to modern ears that might simply sound like religious celebration language — the kind of thing you might expect in a worship song.

But in the first century those words carried much weightier meaning.

The word Hosanna literally means “Save us now.”

It’s not just praise. It’s a plea for rescue.

The phrase comes directly from Psalm 118, which was often sung by pilgrims traveling to Jerusalem during Passover.

It was a psalm about God delivering his people — rescuing them from enemies and establishing justice.

So when the crowd begins shouting “Hosanna,” they’re not just praising Jesus.

They’re asking him to act. They’re saying, “Save us.” “Deliver us.” “Be the king who rescues our people.”

And when they call him the Son of David, they’re making a very specific claim. They’re identifying Jesus with Israel’s royal line — the family of King David — the dynasty God had promised would one day produce the Messiah.

In other words, the crowd is not simply welcoming a teacher. They believe they’re welcoming a king.

And the palm branches reinforce that idea.

In the ancient world palm branches were often associated with victory and liberation.

About two hundred years before Jesus, Jewish rebels known as the Maccabees had driven foreign rulers out of Jerusalem. When they celebrated that victory, palm branches became part of the national symbolism of freedom.

So by the time Jesus enters Jerusalem, waving palm branches is not just a spontaneous gesture of excitement. It’s a political symbol. The crowd believes they’re celebrating the beginning of liberation.

Now Matthew also tells us that people spread their cloaks on the road in front of Jesus.

That might sound like a spontaneous act of respect, but there’s actually a biblical precedent for that too.

In the Old Testament, when Jehu was anointed king of Israel in 2 Kings 9, people spread their cloaks under his feet as a way of acknowledging his authority.

So when people lay their cloaks on the road for Jesus, they’re doing something very deliberate. They’re treating him like royalty.

Which means that in the minds of the crowd, this moment is not subtle at all. This is the arrival of the king.

And Matthew tells us something else in verse 10 that helps us understand how dramatic the moment felt.

When Jesus entered Jerusalem, the whole city was stirred and asked, “Who is this?” (Matthew 21:10)

Matthew says, “the whole city was stirred.”

The Greek word Matthew uses there is fascinating. It’s the word seismos, which is where we get the English word seismic.

It’s the same word used elsewhere to describe something like an earthquake.

So Matthew is telling us something about the atmosphere in the city.

This wasn’t a quiet religious moment. The arrival of Jesus shook Jerusalem.

People were asking questions. Rumors were spreading. Crowds were forming. And everyone was trying to figure out the same thing: “Who is this?”

Now there’s one more historical detail about this moment that many people don’t realize, but once you see it, the story becomes even more interesting.

During Passover week, Jerusalem didn’t just receive one procession into the city.

It received two.

From the west side of Jerusalem, the Roman governor Pontius Pilate would typically enter the city with a military escort.

Historians tell us Roman governors often traveled to Jerusalem during major festivals because large crowds could become unpredictable.

Passover celebrated Israel’s liberation from a foreign empire, which meant Roman authorities were understandably cautious about nationalist enthusiasm.

So Pilate would arrive with cavalry, soldiers, banners, and visible military power. It was a reminder that Rome was in charge.

Now imagine that scene for a moment.

Roman armor shining in the sun.
War horses.
Standards and banners.
Soldiers marching in formation.

That was Rome’s vision of power.

But on the east side of the city, another procession approaches Jerusalem.

Jesus.
No soldiers.
No banners.
No military escort.

Just a rabbi from Galilee riding toward the city surrounded by ordinary people cutting branches from trees.

Two entrances. Two visions of power.

One built on domination. One built on humility.

And the people watching had to decide which kingdom they believed in.

But there’s one more detail in Matthew’s account that hints that something unexpected is about to happen.

Because the king the crowd is celebrating… is not riding a warhorse.

He’s riding something else entirely.

Let’s look again at something Matthew tells us in the middle of the story.

Right after describing Jesus riding into Jerusalem, Matthew pauses and explains what’s happening. Listen to verses 4 and 5.

This took place to fulfill what was spoken through the prophet:

“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.’” (Matthew 21:4-5)

You may notice something that sometimes confuses readers.

Matthew mentions a donkey and a colt, while the other Gospels focus primarily on the colt.

That isn’t a contradiction — it’s actually Matthew being very precise.

In the ancient world, an unbroken colt would often be led by its mother to keep it calm.

Matthew is simply describing the full scene.

But Matthew also does something else here.

He quotes Zechariah’s prophecy in a poetic form that mentions both animals, and he wants his readers to see clearly that Jesus is fulfilling that prophecy.

In other words, Matthew is not just telling a story.

He’s showing us that Jesus is intentionally stepping into a script that had been written roughly five hundred years before Jesus ever entered Jerusalem.

So this moment is not accidental.

Jesus is intentionally staging something. He is deliberately entering the city in a way that echoes this prophecy so that people who know the Scriptures will recognize what he is claiming.

Zechariah had promised that one day Israel’s king would come to Jerusalem.

But the surprising part of the prophecy is how the king arrives.

Not on a warhorse. Not leading an army. But riding on a donkey.

Now that detail might sound strange to us, but in the ancient world it carried a very clear meaning.

When kings went to war, they rode horses.

Horses symbolized military strength, conquest, and battlefield victory.

Archaeology and ancient art from the Near East consistently show kings on horses or chariots when they are depicted as conquerors.

But when a king came in peace, he often rode a donkey.

A donkey signaled that the ruler was not arriving to wage war but to establish peace.

Which means that when Jesus chooses a donkey, he’s communicating something very specific.

He’s saying: “I really am a king. But my kingdom will not come the way you expect.”

Now if we’re honest, this is also the moment where the story becomes unintentionally funny.

Because when we imagine a king entering a city in triumph, we picture something very different.

We picture power.
We picture strength.
We picture a warhorse.
We picture banners and soldiers and the kind of entrance that makes everyone step back and say, “That’s impressive.”

We do not picture… a donkey.

Imagine for a moment if a world leader today announced a victory parade.

The motorcade is ready.
The news helicopters are circling overhead.
Security teams are positioned on rooftops.
The crowd is gathered along the street.

And then the leader arrives… riding a donkey.

At that point the Secret Service would have questions.

And yet this is exactly the moment Jesus chooses to communicate what kind of king he is.

Not a conqueror who imposes power. But a king who brings peace.

And Matthew adds another word from Zechariah that’s easy to overlook but incredibly important.

He says the king comes “gentle.”

That word could also be translated humble.

Which means the defining characteristic of this king is not domination. It’s humility.

And that’s the moment where the expectations of the crowd and the intentions of Jesus begin to diverge.

Because the crowd is hoping for a king who will overthrow Rome. A king who will restore Israel’s national power. A king who will defeat their enemies.

But Jesus enters Jerusalem announcing something very different.

His kingdom will not be built through violence. It will not come through military power. It will come through humility, sacrifice, and ultimately the cross.

In other words, the crowd is celebrating the arrival of a king. They just don’t yet realize that his kingdom will look nothing like the one they imagined.

And if we’re honest, that tension hasn’t disappeared. It still shows up whenever people encounter Jesus.

Because many people are happy to welcome Jesus — at least the version of Jesus they expect.

A Jesus who inspires them.
A Jesus who comforts them.
A Jesus who helps them pursue the life they already planned.

But the real Jesus doesn’t simply affirm our expectations.

He redefines them.

Which means the king the crowd welcomed when Jesus entered Jerusalem… is not the king they thought they were getting.

There’s something else about this moment in the Gospels that’s worth paying attention to, and once you see it, it becomes hard to unsee.

Jesus’ entry into Jerusalem is a moment of enormous enthusiasm.

Crowds are shouting.
Branches are waving.
People are celebrating the arrival of the king.

But if you continue reading the story of that week, something surprising happens.

The crowd disappears.
Just a few days later, when Jesus is arrested and put on trial, the scene looks very different.
The excitement of Jesus entering Jerusalem has faded.
The voices shouting “Hosanna” are gone.
And the public mood in Jerusalem shifts dramatically.

Now scholars debate whether it’s exactly the same group of people shouting “Crucify him,” but the larger point remains clear — the city that welcomed Jesus with celebration does not remain loyal to him when things get difficult.

And when you read the Gospels carefully, you begin to notice something about crowds.

Crowds are often fascinated by Jesus.
Crowds gather around him everywhere he goes.
Crowds follow him across hillsides and through towns.

But crowds don’t always follow him for very long.

In fact, one of the interesting patterns in the Gospels is that the larger the crowd becomes, the more Jesus begins clarifying what it really means to follow him.

There’s a moment in Luke’s Gospel when a large crowd is traveling with Jesus, and instead of encouraging the momentum, Jesus turns to them and begins teaching about the cost of discipleship.

Another time, after Jesus feeds thousands of people with bread and fish, the crowd follows him the next day hoping for another miracle. And instead of repeating the miracle, Jesus begins teaching in ways that cause many people to walk away.

Which is a fascinating leadership strategy, if you think about it.

Most leaders spend their energy trying to build larger crowds. Jesus spends much of his time explaining the difference between crowds and disciples.

And that distinction matters.

Crowds can be enthusiastic.
Crowds can be curious.
Crowds can be emotionally moved in the moment.

But enthusiasm and surrender are not the same thing.

And if we’re honest, we all understand this dynamic.

Crowds can get very excited very quickly.

You see it at sporting events.
You see it at concerts.
You see it whenever a new technology launch convinces everyone that the next version of the phone they already own will completely transform their lives.

Crowds have a way of amplifying excitement.

But excitement is not the same thing as commitment.

And that’s the tension in Jerusalem.

The crowd is celebrating Jesus. But very few people in that crowd yet understand what it will actually mean to follow him.

Because the kind of king Jesus is will only become clear as the week unfolds.

The road that begins with palm branches will eventually lead somewhere the crowd never expected.

It will lead to a cross.

And the kingdom Jesus is bringing will not be built through power or political revolution.

It will be built through humility, and sacrifice, and love.

Which means welcoming Jesus as king requires more than cheering for him.

It requires allegiance.

And throughout the history of the church, one of the ways followers of Jesus have expressed that allegiance publicly is through baptism.

We’ll come back to that in just a moment.

Before we do, there’s one more question Jesus’ entry into Jerusalem quietly asks every reader of the Gospel.

It’s the same question the people in Jerusalem were facing that day.

Are we simply part of the crowd… or are we actually following the king?

Because it’s possible to admire Jesus. It’s possible to find parts of his teaching inspiring. It’s even possible to feel drawn to him in moments like this when we’re reflecting on the story of his life.

But the invitation Jesus extends goes deeper than admiration.

He doesn’t simply invite people to be interested in him.

He invites them to follow him — to place their lives under his leadership as king.

And throughout the history of the church, one of the ways followers of Jesus have expressed that decision publicly is through baptism.

Baptism is a visible way of saying something that’s deeply personal.

It’s a way of saying: “My life belongs to Jesus.”

It doesn’t mean someone suddenly has every question answered.
It doesn’t mean their life is suddenly perfect.

It means they’ve decided who their king is.

And in the early church, baptism often happened very quickly after someone came to that realization.

Not because people were rushing decisions, but because they understood something important — Faith was never meant to stay private. It was meant to become visible.

Which is why throughout the New Testament you see people hearing the good news about Jesus, believing it, and then stepping into the water as a way of identifying themselves with him.

Now if you’ve been sitting here listening to this story and thinking about your own life, you may already know where you stand.

Some of you have been following Jesus for a long time.
Some of you are still exploring what you believe.
Some of you may feel drawn to Jesus but aren’t sure yet what that means. And if that’s where you are, you’re very welcome here.

But there are also some people in the room who believe in Jesus and trust him… but have never actually taken this step of baptism.

Not because you don’t believe. Not because you’re resisting God. Often it’s simply because life moves quickly and the moment never quite seems to present itself.

But today the moment is presenting itself.

And just like the moment in the book of Acts when the Ethiopian asked, “Look, there’s water. What can stand in the way of me being baptized?”

That moment is here in this room… because… look… there’s water.

In just a moment we’re going to hear from someone in our church about how Jesus has been at work in their life.

After they share their story, we’re going to celebrate their baptism together.

And then during our final song, we’re going to leave the water open for anyone else who feels ready to take that step today.

Not pressure. Not obligation. Just an invitation.

Because sometimes the most meaningful response to Jesus is not simply learning more about him.

It’s stepping forward and saying, “I’m a follower of his.”

And if you’re sitting there thinking, “I wish I had known this was happening today… I would have planned for it.” I get that.

But I can promise you this — no one who gets baptized spontaneously wakes up that morning thinking, “You know what would really make today memorable? An unplanned public moment involving a pool of water and a few hundred witnesses.”

That’s not usually how it starts. Usually it begins with a quiet realization that the next step is clear.

Alright, let’s focus our attention to the screen and then we’ll celebrate baptisms together.