When Jesus Doesn’t Meet Your Expectations

Delivered by: Pastor Jesse
Date: March 29, 2026
Length: 26:38 min

Will we follow the Jesus we want… or the Jesus we need?

On Palm Sunday, we look at Jesus’ entry into Jerusalem in Matthew 21:1–11. It was a moment filled with celebration, expectation, and misunderstanding.

The crowds were ready for a king who would defeat their enemies and restore their control. But Jesus arrives in a way no one expected… not on a warhorse, but on a donkey… revealing a completely different kind of power and kingdom.

Scripture References

Matthew 21:1-11 (BSB)

The Triumphal Entry

(Zechariah 9:9–13; Mark 11:1–11; Luke 19:28–40; John 12:12–19)

1As they approached Jerusalem and came to Bethphage on the Mount of Olives, Jesus sent out two disciples, 2saying to them, “Go into the village ahead of you, and at once you will find a donkey tied there, with her colt beside her. Untie them and bring them to Me. 3If anyone questions you, tell him that the Lord needs them, and he will send them right away.”

4This took place to fulfill what was spoken through the prophet:

5“Say to the Daughter of Zion,

‘See, your King comes to you,

gentle and riding on a donkey,

on a colt, the foal of a donkey.’”

6So the disciples went and did as Jesus had directed them. 7They brought the donkey and the colt and laid their cloaks on them, and Jesus sat on them.

8A massive crowd spread their cloaks on the road, while others cut branches from the trees and spread them on the road.

9The crowds that went ahead of Him and those that followed were shouting:

“Hosanna to the Son of David!”

“Blessed is He who comes in the name of the Lord!”

“Hosanna in the highest!”

10When Jesus had entered Jerusalem, the whole city was stirred and asked, “Who is this?”

11The crowds replied, “This is Jesus, the prophet from Nazareth in Galilee.”


Open with:

Zechariah 9:9-10 (BSB)

Zion’s Coming King

(Matthew 21:1–11; Mark 11:1–11; Luke 19:28–40; John 12:12–19)

9Rejoice greatly, O Daughter of Zion!

Shout in triumph, O Daughter of Jerusalem!

See, your King comes to you,

righteous and victorious,

humble and riding on a donkey,

on a colt, the foal of a donkey.

10And I will cut off the chariot from Ephraim

and the horse from Jerusalem,

and the bow of war will be broken.

Then He will proclaim peace to the nations.

His dominion will extend from sea to sea,

and from the Euphrates

to the ends of the earth.


Open with:

Full Transcript

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Lord, we thank you again for this week—an opportunity to focus, to be reminded of what gives us life. What is the hope of the world? What is the hope of our families? What’s the hope for our children?

What’s the hope for our future, God? For the relationships that we long to be restored? This all has its source. The hope of healing and restoration and reconciliation is here in you, in your obedience and your life. So help us to see you clearly. In Jesus’ name, amen.

I watched yesterday with my family—Saturday is family movie night, or day, whenever we choose—and we watched Ender’s Game. Has anyone seen or read Ender’s Game? All right, pretty impressive. I liked it. It makes me want to read the book. I should have read the book first. My kids have read the book.

But in Ender’s Game, there’s this war—or threat of war—from aliens, right? They almost lost to the aliens several years back. So now they’re like, “We learned our lesson. We have to prepare for war.” And the only way to do it is to take the best and brightest of their children and train them for war to defeat these aliens.

Everything around their society is anchored in and focused on this threat of war with the aliens—training the future to fight these aliens.

And they’re looking for kind of a messiah figure, right? Every story is the big story of the Messiah. They’re looking for a messiah figure, and they find it in this young boy named Ender. He is recruited, pressured, trained, and made to be this brilliant strategist.

I’ll try not to give anything away—no spoiler alerts—but the trainer, the recruiter, the one responsible for his training, is pushing and pushing and pushing. They’re having a conflict on ethics, right? The ethics of war.

How are they going to defeat the aliens?

And the general—or whoever this guy was—says, “By any means necessary. Winning is all that matters.”

And Ender says, “No. How you win is all that matters.”

How you win is all that matters.

The crowds in our passage this morning in Matthew—there are people desperate to win. There are people desperate for rescue. They are suffering.

As a Jewish people in Jerusalem in the first-century Near East, they are occupied by the Roman Empire—a cruel ruler. They are overtaxed. They are starving. Their children are starving. Life expectancy is not much past the 30s. Infant mortality is super high.

They are poor. They are oppressed. They are squashed by occupying forces, by the Roman Empire. And they are hungry for a messiah. They are hungry for rescue—for a Savior.

All of their expectations are on this promised Messiah who would come and rescue them from the Roman Empire, from their enemies—who would defeat their enemies and bring them back into autonomy and into control.

And as Jesus comes into the city, he comes into a people hungry to win, ready to win by any means necessary.

“I want to win. I want to win, and that’s all that matters.”

And so Jesus says, “No. Winning matters—but how you win, how you defeat evil, how you conquer your enemies, how you treat your enemies matters more.”

How you win matters.

And so, in the same crowd—as the crowd cries, “Hosanna!” which means “Save us”—they say, “He comes in the name of the Lord.” They praise him, and they put all their hopes in him.

And these same will be the ones who cry, “Crucify him!” just six days later. The same crowds that said, “Hosanna! Save us!”

All their expectations are on the Savior who will help us win and defeat the enemy. When he goes toward the cross and he is not winning as they expect him to win—in fact, it looks like he’s losing—they turn.

And the same crowds who said, “Hosanna,” say, “Crucify him!”

And so, holding these palm branches today, we identify with the crowds. In Matthew 21, we identify with a people hungry and desperate for a Savior.

We live in a world full of violence. There are wars happening. There’s tension in our country and our families, and we just want out. We want resolution.

And we are tempted to pursue messiahs—or even to project onto Jesus—a hope that all that matters is winning, and it doesn’t matter how.

And Jesus is always inviting us back to, “No. Winning—yes, we will win—but how you win matters.”

And Jesus leads us into that way.

And so we want Jesus to rule and exercise power in the ways that make sense, in the ways that keep us in control, in the ways that crush our enemies.

But Jesus is always subverting that desire and saying, “Follow me—the one who rides in on a donkey.”

So can we read this once more? Because we want to get this straight.

You can open your Bibles in your apps, or if you have the old-style Bible with pages, please open that. That’d be even better.

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

I would not want to be a disciple—someone who is kind of hyper-concerned about what people think of me. I do not want my Jesus to say, “Go tell a random stranger you need his donkeys.” It’s just weird. Awkward.

I don’t know what they were thinking, but they went. They did it.

But he has a reason for doing this, right? He says this took place to fulfill what was spoken through the prophet Isaiah.

I want to read the prophecy from Isaiah—this is the quote of it. Here’s the fuller quote from Zechariah 9:9–10. This is the prophecy, again, of the hope of the Messiah they’re waiting for:

“Rejoice greatly, Daughter Zion! Shout, Daughter Jerusalem! See, your king comes to you, righteous and victorious, lowly and riding on a donkey, on a colt, the foal of a donkey.

I will take away the chariots from Ephraim and the war horses from Jerusalem, and the battle bow will be broken. He will proclaim peace to the nations.

His rule will extend from sea to sea, and from the river to the ends of the earth.”

And did you hear that? Do you see this?

The expectations for what kind of king—and how the king would rule and reign and win—were already set up for hundreds and hundreds of years.

The bow will be broken. The war horse will be taken away. The war horse will be cut off.

The king will not come with a cavalry. This king will not come with military might.

He comes with peace—peace to the nations. Not just peace for the insider group. Not just peace for the Jewish people, but peace for everyone, for all nations.

So there are two kinds of power.

Jesus has them go get these colts. He’s being very deliberate. A biblical scholar says he’s actually engaging in prophetic theater. He’s very intentional.

Here he is—he tells the disciples to go get these two colts, this donkey and this colt—and he’s going to ride on them. He has in mind this passage in Zechariah.

Now why would he do this as he comes into the city, riding on a donkey?

He’s doing this very deliberately to set up a contrast between him—the way he will be king—and the way Rome and Pilate, the Roman leader of that region, would be.

Often, Roman emperors and dignitaries would come into the city during festivals riding not on a donkey, but on a war horse.

They would ride with military procession, with armor gleaming in the sun, with battle standards—the flags whipping in the wind. And there was a very strong point being made.

And that point is this: “We are in control. We rule. We dominate. We have the power.”

So Pilate rides in from the west—war horse, soldiers, the full display of Roman imperial power. It says, “We are in charge.”

Power flows from the top down, enforced by violence or the threat of violence. It demands submission.

Now Jesus says, “Go get me a donkey.”

There’s this passage in Zechariah that all the Jewish people would know and have in their minds. They have all this expectation that he will come like Pilate—but then he subverts it.

He reminds them of Zechariah.

Jesus rides in from the east. He borrows a donkey. He’s surrounded by peasants from Galilee. They lay down their coats because they have nothing else to give. They have branches, shouting a word that is simultaneously a prayer and a declaration:

“Save us! Save us now!”

Gregory Boyd, the theologian, describes this as the difference between “power over” and “power under.”

See, Jesus is all-powerful, but he occupies and inhabits power in a different way—in a way we don’t expect kings to exercise power.

He models power and authority and kingship in a different way.

His power is exercised from under people. It’s in service. It’s a power that lifts up. It’s in humility. It’s in self-giving love.

The kingdom of God—see, what Jesus says—the kingdom of God is not bigger and better. It’s not powerful in the sense that you take the most powerful ruler you can imagine and just exaggerate it and say, “God is that much more powerful, that much stronger, that much more destructive.”

We don’t take worldly conceptions of power and multiply them and make that God’s power.

Jesus says, “No. Power in the kingdom is completely turned upside down.”

Power is occupied and inhabited in a completely different posture. It still defeats evil—but not in the way of evil.

It changes things. It wins in a different way.

How you win is as important as that you win.

So here are three primary ways the crowds’ expectations—again, waving the palm branches, hoping for a Savior, longing that Jesus will crush their enemies and be stronger than Pilate in the way that Pilate is strong—are shattered as the week goes on, as he heads toward the cross and is crucified.

There are three ways the reign, power, and authority of Jesus subvert the worldly conception of power—our expectations of what victory and authority look like.

First of all, the way that Jesus wins is he loves and forgives his enemies.

First of all, the way that Jesus wins is he loves and forgives his enemies.

The crowds expected Rome to be judged, enemies to be crushed, vengeance to be delivered. But Jesus rides into Jerusalem on a donkey—not to destroy his enemies, but to die for them.

And that’s important. He doesn’t just die for his inner circle. He doesn’t just die for the Jewish people. He doesn’t just die for his disciples so that the enemies would be vanquished.

He ends up dying for everyone—the enemies included.

And he doesn’t just die—but from the cross, do you remember what he says?

As he’s pinned to the cross, as he’s been beaten, as he has a crown of thorns, as people mock him and spit at him, as he’s abandoned by all those who had just previously praised him, he says:

“Father, forgive them, for they know not what they do.”

This is not the king they wanted. This is not the king they expected. This is the king they rejected.

Because—and let’s make it about us—we want a Jesus who takes our side. We want a Jesus who validates our anger. We want a Jesus who justifies our hatred.

But the true King says: “Love your enemies. Pray for those who persecute you. Forgive those who do you wrong.”

Love them. Don’t tolerate them—love them. Don’t avoid them.

It’s this active step toward people.

So the reign of Jesus surprises us. It surprises us—and it’s still surprising us. We forget.

Because he refuses to hate the people we hate. He refuses to dehumanize the people we fear. He refuses to destroy the people we think deserve it.

Instead, he forgives them.

And I think we all—you know, on both sides of the political aisle, both sides of the news media—they’re both inviting us to dehumanize those we fear. They’re both inviting us to hate those who hate. They’re both inviting us to see Jesus as on our side.

And that, through political power, through violence, through war—whatever—we will win.

And I think Jesus is reminding us: no. The way that we win matters just as much as that we win.

And Jesus loves and forgives his enemies. He’s inviting us into the same.

Second, where he surprises us: Jesus brings peace through self-sacrificial love.

The crowd cries, “Hosanna! Save us!” And what that salvation looks like for them is political victory, national restoration, visible dominance—being put back into control over their enemies.

But Jesus again enters on a donkey, not on a war horse. He enters surrounded by peasants, not by military might.

And the king does not come with a sword—he comes bearing a cross.

And so the cross redefines peace and how peace is won.

Winning the fight for peace is not winning by any means necessary. It’s not silencing the opposition. It’s not eliminating threats.

Peace is absorbing.

This is what Jesus does on the cross—he absorbs evil without returning it. He takes on violence into himself and doesn’t give it back.

He exhausts evil.

He absorbs evil without returning it. He takes on violence into himself and doesn’t give it back. He exhausts evil.

There’s this wonderful—I don’t know if you’ve seen it—what is the movie? It’s about… man, I can’t remember the movie, but it’s coming to my mind. There’s a POW, and it’s a true story. He’s in World War II, in a Japanese prisoner-of-war camp.

And there’s this one general who has it out for him and just lets him have it all the time—every day—just beats him to within an inch of his life almost every day.

And the climactic scene of the movie is this: this Japanese soldier has the man hold up a heavy log above his head. And he has another soldier point a gun at him and says, “If you drop that below your head, we will shoot you.”

And the guy holds it, and holds it, and holds it. And he’s malnourished, and he’s weak, and there’s no way humanly that he should be able to hold it up—but he holds it.

He holds it until the sun goes down and into the night—until the man is finally exhausted himself and calls the soldier to lower his rifle and sends him back to his cell.

He exhausted evil through his endurance.

And this is what Jesus does on the cross. He exhausts all the evil, all the violence, all the rage that the enemy had to unleash on him. He absorbs it. He takes it. He exhausts it until it has no more energy left—and it’s defeated.

So we learn that the love of God, the power of God, is kenotic—that’s the Greek word—self-emptying. It’s a self-emptying love.

The liberating rule of Jesus is kenotic. It’s self-giving. And that’s not what we expect.

So Jesus does not bring peace by overpowering his enemies in traditional ways. He brings peace by giving himself for them.

And that kind of peace feels like weakness. That kind of peace scares us. And that kind of peace looks like loss.

But it actually is the power that heals the world.

All right, third and last: Jesus overcomes evil by laying down his life.

The crowd expected evil to be defeated by power. They wanted Jesus, the Messiah, to ride on a war horse—to defeat by domination, by righteous violence, by revenge, by vengeance.

And Jesus defeats evil in the way no one expected—not by taking life, but by giving up his life for us and for his enemies.

And we have to be honest here—it still appears this way, right?

The cross—it looks like evil wins, doesn’t it? It looks like evil wins. Rome is still in power. Jesus is dead. Hope is gone, it would appear.

It looks like the crowds, at this point, are right for saying, “Crucify him.” It looks like they’re justified, because their definition of victory could not recognize the true victory.

And I don’t want to be too hard on them, because he was literally dead. It literally looked like he lost.

But the cross is not defeat.

The cross is evil exhausting itself, sin being absorbed, death being undone by death. Jesus goes into death and out the other side, destroying death through his defeat—through his subjection to it.

So N.T. Wright says, “The cross is the moment where God defeats evil—not by violence, but by love.”

So let’s turn from the story of the crowds to our story.

We’re not just observers, right? We are participants. Every week—and maybe in our cars, to a CD or whatever—we’re praising God. We’re saying, “Hosanna, hosanna in the highest. Blessed is he who comes in the name of the Lord.”

But often, when we are praising Jesus, we are projecting onto him all of the expectations that we have.

We want Jesus to rule and to win in the ways that the world wins—in the ways that we feel most comfortable with, in the ways that keep us in control, in the ways that reduce our suffering, in the ways that reduce our need to love and to respond with forgiveness and patience and joy and love.

We want him to overpower and lead us into victory in the ways that we understand—victory in the ways the world conceptualizes victory.

But the king we want in those moments is not the king that can save us. It’s actually the king that will destroy us.

If that’s our Jesus, then we are continuing down the path of destruction. And we see this in our world over and over and over again.

Only the king that Israel did not expect—only the king that we do not expect—can save the world.

Only the king who is still king—Jesus is still king—who is still forgiving his enemies, still bringing peace through self-giving love, still overcoming evil by laying down his life.

And so that’s good news.

That’s good news because that means your sin does not disqualify you. That means that Jesus will forgive you. That means your failure doesn’t define you.

That means even your misunderstanding of Jesus—even the ways that you want him to crush others and other people—that means you will be loved regardless, and that he will be patient and kind.

He will come up underneath you with power to be transformed.

And it also means that your enemies are not beyond redemption—that Jesus is not just your God and your Savior, but he is all people’s Savior—all nations, all tribes, all tongues, every person’s Savior.

So the question is not: will we praise Jesus? We do that every week.

The question is: will we follow the King we did not expect?

Will we follow Jesus who crushes our expectations?

Will we forgive like him?

Again, this isn’t just intellectual—it’s: will we follow Jesus in the way of Jesus?

Will we be a cruciform people? Will we be a people that takes the shape of the cross—that takes the shape of a Savior who loves his enemies, who forgives his enemies?

Will we forgive like him? Will we love like him? Will we lay down our lives like him?

So that’s the question.

So I want to invite you to stand, and I want you to hold these palm branches as a way of, yes, praising Jesus, but also of acknowledging our tendency to want Jesus to meet our expectations.

And as we sing the song “Hosanna,” as we enter into the voice of the crowds, as we praise Jesus—may we praise the Jesus who leads us into love, who leads us into forgiveness, who leads us into coming up from underneath people and lifting people up rather than crushing them.

Let’s sing together.

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