Jesus Knew You'd Be Disappointed And Rode In Anyway |03.29.26|Holy Week 2026 pt.1

There’s a quote I heard recently from Brene Brown. It says, “Expectations are resentments waiting to happen.”

Does that feel true?

Think about the last time someone didn’t show up the way you expected. Maybe it was your parent, or a friend, or your spouse. Maybe it was even God.

You had an expectation about what they were going to do, how they were going to act… and they didn’t. Reality didn’t match the picture you had in your head.

That gap – between expectation and reality – is the gap where disappointment lives. It’s where bitterness and resentment grows. That gap is where some of us have been sitting for a long time…

But the gap between expectation and reality is also where some of the most important parts of our character are formed. It’s also where our spiritual life can grow… if we don’t run from the disappointment.

The gap is where trust is tested. It’s where lament is practiced. It’s where faith that holds fast is developed. It’s where the shallow and flimsy stuff gets burned off so that something more real and lasting can take its place.

The question today isn’t whether you’ll ever experience the gap between expectation and reality… it’s what you’ll DO while you’re there.

Because when was the last time you were sitting in church and we admitted together that sometimes the biggest disappointment we’ve experienced is actually from God?

You thought he was going to do something, and he didn’t. Or he did it differently than you had hoped. Or he hasn’t done anything yet.

And so the gap between your expectations, your hopes, and what has actually happened is leaving you confused. Maybe a little angry. Maybe a little shut down and distant.

[Scripture Ref]

Well, what we’re going to see today in our Jesus story is that the crowd who were shouting “Hosanna!” had their own expectations of what Jesus was going to do. And they were wrong. They didn’t see what was coming for Jesus.

Jesus knew exactly what was coming, and he knew it was what the crowd was hoping for, but he rode in anyway — weeping, determined, and fully obedient to God’s plan.

So open your Bibles with me to Luke 19 (p???). This picks up on the day known as Palm Sunday. It was actually the beginning of the week leading up to the Jewish festival of Passover, where Jews remember when God rescued them from slavery in Egypt. (we didn’t start calling it Palm Sunday until after this happened)

During the festival of Passover, the city of Jerusalem would get a huge influx of travellers coming into town for the celebration. So the normal population would be around 50,000 people (like the population we have here in the Sauk Valley), but during Passover, it would surge to over 150,000 people.

So, you’ve got a huge amount of people coming to remember and celebrate the fact that God was a rescue and savior… but this is happening WHILE they are CURRENTLY under Roman oppression.

So they are remembering when God rescued them generations ago, AND they are crying out, asking God to rescue them again. They are waiting expectantly for God’s promised savior, the Messiah.

And many of the people have been hearing about this Jesus guy. He seems to fit the bill. And today, he’s going to enter into town from the east, down the Mount of Olives, which is the very place that the prophet Zechariah said God would arrive from… PLUS he’s going to be fulfilling a couple other prophecies, and his disciples are going to be building up some anticipation with how they enter with him. So as we read together, let’s STAND to hear God’s Word…

[Luke 19:28-38]

[Luke 19:29-30]

It’s Passover in Jerusalem. The amount of people has TRIPLED. The Roman soldiers who are there to enforce laws and taxes are under extra pressure with all the extra people.

The Jews are all wondering, “Is THIS the moment that God will finally come rescue them from their great enemy, Rome? Is this when he will finally save them?”

Everyone is expecting something. They’re all waiting for something to happen.

And it’s clear that Jesus knows exactly what is coming, because he’s orchestrating moments. He has his followers get a donkey for him, which is a fulfillment of a prophecy in Zechariah 9:9.

See, Jesus wasn’t “vamping.” He wasn’t “going with the flow.” He already knew the donkey would be there. He already knew what the owner of the donkey would say. He’s not scrambling, he’s setting the stage for his entrance.

[Luke 19:37-38]

And by doing that, Jesus is also coming up against some very real and very different expectations for what this all means.

His own disciples assume that Jesus coming as the Messiah, as the Savior, means that he will establish himself as the king of Israel.

The crowds assume that Jesus will overthrow the Roman government and finally rescue them from that oppression and enemy.

The religious leaders assume that Jesus is going to TRY those things, but get crushed and fail just like previous wannabe revolutionaries.

And as Jesus approaches Jerusalem, the crowds are singing the traditional psalms they sing at Passover every year: “Hosanna” - save us.

And they’re singing Psalm 118, “Blessed is he who comes in the name of the Lord.”

Actually, this short clip helps us get a picture of how all the different expectations clash:

[VIDEO]

[Luke 19:38]

“Blessed is he who comes in the name of the Lord.” But, again, their praise that they are directing at God (and at Jesus) is combined with their expectation that he will do what they expect him to do.

But you and I know that Jesus didn’t come to overthrow ROME and crown himself king of Israel… His plan is so much bigger.

He came to overthrow sin and death and crown himself Lord of life and King of all creation.

But that means that Jesus’ “triumphal entry” into Jerusalem is a road that is leading him towards his betrayal, arrest, and brutal murder. And the people’s hopes and dreams are going to be crushed along with Jesus’ body.

Because the gap between their expectations and the reality of God’s plan is a pretty wide gap. And they are going to be drowning in that disappointment.

And this is important for us to realize: because WE can genuinely praise Jesus and try to follow him… and STILL have the wrong picture of him. We can still have the wrong expectations of him.

The crowd wasn’t being fake. They were fickly hypocrites: praising him one day and shouting for his crucifixion a few days later for no reason.

They were genuinely celebrating the king THEY IMAGINED. Just not the king that Jesus is.

They expected a path of victory and success. But Jesus walked the path of servanthood and suffering.

We can fall into that trap as well. We can show up to church, sing all the songs, mean every word we pray… and STILL have expectations for Jesus that are more about what WE WANT that who HE IS.

But Jesus KNOWS the wrong expectations about him, and he still pressed forward. Jesus KNEW all that was coming, and he still chose to step forward in obedience to God’s plan.

[Luke 19:41,43]

And it tore him up. As he’s approaching Jerusalem, coming down the hillside from the Mount of Olives and up into the city… Jesus wept over the city.

Now, the word that is used here for “wept” isn’t talking about a little tear at the corner of his eye. He’s not getting a “little misty.” The word used is talking about loud, audible weeping. It’s the same word used for “uncontrolled grief.”

While everyone around him is celebrating and loudly cheering for their expectations of a conquering king, Jesus is sobbing… absolutely broken.

But he’s not crying because things have gone wrong. He’s crying because he can see what is going to happen in the next few years for Jerusalem, and the crowd has no idea.

They are feeling the weight of Roman occupation, but Jesus foretells that the Romans will come and lay siege and end up completely destroying the city. And that actually happened a couple decades later in 70 AD. The city fell, the people were scattered, and it was awful… all because they were looking for a different kind of king, and they missed the one who was actually there.

And I just want to sit with this for a moment, because Jesus is weeping, but he doesn’t walk away. He doesn’t stop. He sees how the people are misunderstanding him. He sees their eventual destruction. He even sees how he’ll have to endure intense pain and suffering in just a few days… but he rides into town anyways.

Jesus isn’t the conquering king they thought they wanted. He’s the king who loves deeply enough to grieve, and still steps forward into what needs to be done.

[Luke 19:45-46]

And one of the first things he does is “clear” the temple. And what he says while he’s doing this gives us a better understanding of what he’s doing, because he quotes the book of Isaiah when he says that “[God’s] house is to be a house of prayer for all peoples.”

It’s a beautiful section of Isaiah, where God is proclaiming that all the foreign people outside of the Jewish people will also be included in God’s mission of grace. He’s calling all people to himself (and that includes YOU and me!), he’s reaching out to the Ones who are far from him, and he’s adopting them into his family.

And so, when the temple was built, they decided that the outer courtyard was the spot where non-Jews could come to pray and worship God. That would be like the parking lot or the little breezeway inside the front doors here at New Life.

But you had to be a jewish man or woman to go into the inner courtyard (like our atrium out there), and you had to be a jewish MAN to into the section closest to the Holy of Holies in the middle, where only the high priest could go.

But over the years, the temple leaders (who had been put in power by the Romans) had allowed the outer courtyard for the Gentiles to become overrun. And I’m just talking about regular parts of the temple worship system.

Because when you travel a long way to give a sacrifice to God, you probably aren’t going to bring the goat with you. You’ll bring money, but when you get to Jerusalem, you’ve got to exchange your Roman money for temple coins, because Roman money can’t be given as an offering to Yahweh. And then you can use that money to buy the animal you need for the sacrifice.

But OF COURSE, there were some injustices happening. Exchange rates got a little higher over time, a larger cut was being kept back for the people in the system and the temple leadership over time… and during festivals, when there were SO MANY people coming into town, they had to stock up on animals…

So now the whole courtyard is PACKED with animals, money changers, guards for the money changers, people arriving, people leaving… it’s crazy.

And if you were a Gentile who was a devout follower of Yahweh, and you came all the way to Jerusalem to pray and give honor to God, and you show up, and you’re supposed to try and pray in ALL OF THAT?!

[Luke 19:47-48]

So Jesus causes a ruckus, creates some room finally, and then sets up shop teaching the ones gathered THERE (the outsiders, the non-Jews) all about the kingdom of God.

But yet again, Jesus isn’t living up to the expectations that are put on him. THEY wanted a Jewish king who was going to make Israel great again and get rid of the awful Roman regime.

But in reality, he was creating a pathway for all people to be able to connect with God, through him.

[Our Disappointment]

And as we’ll see over the next few days, as we walk through Palm Sunday into the Last Supper and to the cross on Friday… the path that Jesus is walking is one that we would never have chosen.

But we want a leader who will go to war for us to defeat our enemies (that we see).

We want a Savior who saves us from all the discomfort we face.

We want a king who leads us in the ways that WE prefer.

But here’s the truth from this story that still applies to us today:

Our disappointment in God usually says more about OUR expectations than about God’s faithfulness. [...]

Have you felt disappointed in God? Have you wanted him to answer a prayer, to create an opportunity… and it hasn’t happened yet?

In my role as a pastor, I get to talk to a lot of people who are struggling with their faith. Because God hasn’t shown up like they expected. Because things haven’t come through like they hoped.

And most of us do one of two things when we experience that gap between our expectations and reality:

We either fill it with a story, like “God let me down… God doesn’t care… I just need to figure out how to DO the right things to make God hold up his end of the bargain…” …or…

We just go numb. We stop expecting God to show up at all. Because, that way, we won’t be disappointed again.

But our disappointments say more about the expectations we’ve been carrying. It doesn’t actually give us an accurate view of God’s faithfulness.

And we see this with Jesus: the crowds were celebrating, but they just expected something different than Jesus was there to deliver. But when Jesus didn’t become the king they wanted… when he was arrested, condemned, and crucified… that disappointment broke them.

Now, you and I know that God didn’t fail when Jesus died. It was part of his plan! Because he wasn’t there to defeat the enemy Rome. He came to defeat our enemy DEATH!

The crowds couldn’t see it. Even the disciples couldn’t see it.

But Jesus could see it. Jesus knew exactly what was coming, and he chose obedience anyway.

The path to the cross wasn’t a surprise. It was a strategy. And it Jesus walked toward the cross with confidence and intentionality, then we can trust him with whatever WE’RE facing.

Because when God doesn’t show up in the way we expect… whether it’s in our marriage, or in our health, or in our finances… that’s not evidence that God has abandoned us! It doesn’t mean that God has lost control of the situation!

Because he’s able to see things we don’t. He’s able to be working behind the scenes, and we just don’t see the full picture yet.

So if you feel disappointment in the ways that God hasn’t come through for you yet, just know that you are not alone! Jesus walked THROUGH our disappointment to secure our rescue.

Jesus willingly endured scorn and shame and suffering because he knew that he could defeat death and beckon us to follow HIM as the way, the truth, and the life.

[Tell someone]

So where have you felt let down by God? Not in theory, but specifically.

Is there something you’ve prayed for that didn’t happen?

Is it a direction that you thought God was leading you, but it ended up going sideways?

Maybe you feel the disappointment of being in a season that you thought would be over by now?

Listen to me: you don’t have to clean it up or make it sound spiritual. All you have to do is name it. In your head, right now, name the way that you have felt let down by God. That’s the first step of stepping into the light and the truth of your experience.

But I think your next step after that is to tell someone else this week. Tell a friend you trust. A spouse. Tell someone in your life group.

Now, you’re not telling them to complain or to get sympathy (although, they will probably listen in a way that helps you feel less alone!)

They might just listen. They might lament with you. They might thank you for just being honest…

But you need to tell someone else about the way you are carrying disappointment in God SO THAT they can help remind you of his faithfulness!

Because disappointment FESTERS when it’s kept a secret. And one of the GIFTS of being a part of a church family is that there are people here… there are people in your life… who have been through that gap between expectation and reality.

They’ve been through it and they’ve come out the other side trusting God even MORE, not less. And you need them to speak into your story. You need them to remind you of how God has shown himself to be faithful all throughout history. You need them to point you back to the faithfulness of God so that you can hold tightly to Jesus in the midst of this disappointment.

[END]

And we CAN hold tightly to Jesus, because he’s PROVEN himself to be trustworthy.

The parade at the beginning of Palm Sunday didn’t go straight to the king’s palace to enthrone Jesus.

It led to the cross. And Jesus KNEW that when he got on the donkey that day.

He wept over Jerusalem, because it represented his people that he loved. And yet he chose to keep going with the path laid out before him (even when every human instinct might have turned back) because he was going to absorb once and for all the darkness that threatens us every day.

He was going to humble himself, becoming obedient to death, even death on a cross!

Therefore, God exalted him even more highly and gave him the name that is above every other name, so that at the name given to Jesus every knee should bend, in heaven and earth and under the earth, and every tongue should confess that Jesus Christ is Lord!

When the crowds were shouting “Hosanna” that day, they didn’t even know how FULLY Jesus WAS going to save them.

And when we are going through a season of darkness, when we are going through disappointment, when we are feeling out of hope… we can trust that we have a Savior who has already gone to hell and back to make sure we can have life… life to the full!

Hosanna. Come save us, Lord Jesus! Amen.