Speaker: Tim Bollinger
Scripture: Matthew 21

From the series Holy Week & Easter 2026

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Full Sermon Transcript

Hey, good morning. It’s good to see all of you today. If this is your first time here, or maybe this is your first time attending Holy Week here at Shepherds Gate, we’re so glad to have you here.

And look, you all figured out that the service started at 1030. Which, what time is it right now? Is it 11? What time is it? I don’t even know. 1046, so just so you know, there might be some people that are gonna be coming in in about 15 minutes, okay? So, just what happens when you change service times.

But we’re glad that you’re here, and my name’s Tim. If I haven’t had the chance to meet you, I get the privilege of being one of the pastors and staff members here. As today, we kick off Holy Week 2026.

Can you believe that? In March, it’s March. It’s this weird March day with the fifth Sunday of the year. But it is a very important time in the life of the church.

And maybe you didn’t grow up in church, maybe you’re new to the Bible, and you’re maybe wondering, what’s the big deal? Why do we make such a big emphasis on Holy Week? And if you kind of just pull back for a moment and look at maybe some of even the other major religions of the world, especially those of you that have been with us the last 12 weeks, we’ve been in Exodus. We got through the first 12 chapters of Exodus. And wouldn’t you know where we left off last week actually dovetails perfectly into what we’re doing this week.

Because the Feast of the Unleavened Bread and Passover is actually a week-long festival. And so our Jewish friends will actually be celebrating that later this week. That’ll kick off for them on Wednesday.

In Islam, they have Ramadan, which is actually a month long. Wouldn’t it be great if we had a month-long Holy Week? Anyone wanna sign up for that? And they actually just finished as well. So they did it the middle of February to the middle of March, which means if you have Muslim friends, you should invite them to our Holy Week services.

This is where you say amen. Amen. Amen, because we believe that Jesus is the one true God.

He is the Savior of the world, and it’s not Muhammad and what they believe in. And so we want them to know who Jesus is, amen. So what a great opportunity for you to do that as well.

And for us as Christians, Holy Week, this opportunity to pause our lives for one week, one week out of the year. The other big time in the life of the church is when? Christmas. Now, if you’re new to Holy Week, let me just walk you through this for a moment, okay? Today, we’re gonna be looking at Palm Sunday because we have palm branches, and this is when Jesus gets on the donkey and he heads into Jerusalem.

We’re gonna be looking at those passages today. And then Monday, Jesus, when he’s in Jerusalem, actually goes to the temple and he’s a little angry. He actually flips some tables over and he has some kind of some interactions with some people, and he tells them that his house is to be a house of prayer.

Tuesday, he goes back into the temple. There’s some more teaching that takes place. Wednesday is kind of cool.

If you didn’t know this, they call it Spy Wednesday. This is what the church has historically called it. And this is where Judas at some point has to go and agree to betray Jesus.

Maundy Thursday, maybe you’re new to a church that celebrates Maundy Thursday. We have a Maundy Thursday service here. And this is when Jesus institutes the Lord’s Supper.

This is when he takes the Passover meal and he fulfills it in his words. Of course, Good Friday is when Jesus goes to the cross for us. Saturday, he rests in the tomb.

And then Easter Sunday is when we celebrate that he did come out of that tomb and he declared victory over sin, death, and the devil for you and for me, amen? So I was thinking about this. What if we had worship services every day of the week for Holy Week? Would you come? You would? All right, see, look at that, because the staff thinks I’m crazy around here. Because we’re already gonna have 12 services in eight days.

And what I find fascinating, if you don’t know, and if you’re new to scripture, that out of the four gospels, there’s four gospels, Matthew, Mark, Luke, and John. It’s the beginning of the New Testament. They give the account of the birth and the life and the teachings and the death and the resurrection of Jesus.

Now, if you take all four of those gospels and you put them together, only 2% of what has been written is about Jesus’ birth. Following me? Which if there’s 2% written about his birth, what does that leave left? 98%. Out of that 98%, you can cut it in half, pretty much, okay? Half of that actually talks about the three years that Jesus spent doing teachings and healing people and all the incredible ministry that he did.

The other half of that 48% is about this one week. And so if God is the author of the Bible and God is the author of scripture, how important do you think Holy Week is to him just based on the percentages of what he wrote in the scriptures? A lot. I mean, that’s a lot to dedicate to this week.

And that’s why we take it so seriously. In fact, if you didn’t know, for the first 300 years of the church, they didn’t even celebrate Christmas. They only celebrated Holy Week and Easter.

So really, we’ve only been celebrating Christmas for 1,700 years. We’ve been celebrating Holy Week and Easter for 2,000 years. And that is why, because without the resurrection, our faith is completely useless.

And so I wanna invite you into this Holy Week like never before. And you’re gonna see that as we walk through these passages together. So Palm Sunday, as we kick this off, Jesus’s final week, in Matthew chapter 21, this is what he tells us, that as Jesus and the disciples are approaching Jerusalem, they came to Bethpage on the Mount of Olives.

So they’re walking toward Jerusalem and they stop here in this specific spot. Now, here’s what’s interesting. The three years that Jesus did ministry, almost all of it was out in the country.

He spent very little time in Jerusalem, which was the capital city. And so you imagine as he’s got his entourage, his disciples, as they’re heading toward the city, they don’t actually know what’s about to happen. They think they’re just going to celebrate the Passover Festival, which is what they have done their entire lives and all the generations before them.

Jesus knows exactly what he’s going to do. And he’s gonna orchestrate all of the events in fine detail so that he gets the outcome that he wants at the end. And so when they stop on this spot, it says Jesus sent two disciples to go into the village ahead of them.

And at once you’re gonna find a donkey tied there with her colt by her. So how many animals are there? Two, not one, no matter what your children’s Bible says, there’s two donkeys. And the only reason I tell you this is so when you’re playing one of those Bible trivia games with your family and it asks how many donkeys were there, you’re gonna say, and you’re gonna win the game, okay? So untie them and bring them to me.

And if anyone says anything to you, if anyone’s like, what are you doing stealing? I mean, borrowing those donkeys, say that the Lord needs them and he will send them right away. And I was actually thinking about doing this this week. I have a friend, he works at a bank.

And I was wondering if I just went into his bank and said, hey, I need $2 million for a building program that I have going on at my church. And the Lord needs this $2 million because we’re building his church so that people can come and worship him. Do you think he would release that money to me? You don’t think he would, even if I said the Lord needs it? What if I walked into a car dealership and I said, I wanna test drive the best car that you have on this lot.

And by the way, I have no idea when I’m bringing it back, but the Lord needs this car. How many of you think how quickly they would be calling the cops on me, right? It’s just amazing that Jesus, think about this, he’s already placed it in the heart of whoever owns these animals and that they’re gonna freely release these animals to the disciples. Matthew tells us this takes place to fulfill what was spoken through the prophet.

Your king is gonna come to you, but he’s gonna be a gentle king, riding on a donkey on a colt. There’s your two animals again, the foal of a donkey. Now, historical context in all of this, if you didn’t know this, if Palm Sunday is new to you, a king at this time would ride into Jerusalem on a horse if they wanted to create conflict.

And by conflict, I mean declare war. And so people know that if they saw somebody coming in, either they’re declaring war or they’re declaring victory over a recent war. A king would then come on a donkey, very specific animal, if he wanted to announce that he was coming in peace.

And so this Palm Sunday, we’re kind of going back and forth between these two concepts of conflict and peace and who’s bringing conflict and who is actually bringing peace. Well, the disciples did exactly what Jesus told them to do. They went and got the donkey and the colt and they placed their cloaks on them.

So they took off their jackets and now they’re placing them on there so that Jesus can sit on top of them. Not only so, but a large crowd also spread their cloaks on the road while others cut branches from trees and spread them on the road. This is what we just sang about.

This is what we just saw in the videos during those songs. And so we have this image now of not just the disciples, but men and women and children who also equally important, they were on their way into Jerusalem to celebrate the Feast of Unleavened Bread and to celebrate the Passover meal. And so there’s this large crowd of Jews had actually found out that Jesus was there.

And not only did they wanna see Jesus, because by now rumors had spread and his popularity had grown so greatly, they also wanted to see who? What does it say in the passage? Lazarus, whom he had just recently raised from the dead. So hold on to this for me, because this is important. A very short time before Palm Sunday, Jesus was with his disciples and he gets word that Lazarus is ill.

And they tell him, Jesus, you need to get here, you need to put your hand upon him and heal him so that he’s better, that he’s made well. And Jesus does the exact opposite. In fact, he doesn’t wait one day, he doesn’t wait two days, he doesn’t wait three days, he waits four days after Lazarus has already passed away from his illness.

And people are mesmerized by this. In fact, Martha is the one that told Jesus to come quickly and he didn’t do that. And she kind of gives it to Jesus.

She’s kind of really upset with him. And when he gets there, when he gets there and he sees the situation that’s happening, he enters into that moment with them because he’s fully man, it says that he weeps with them, but more importantly, he calls Lazarus out of that tomb. And he creates this unbelievable miracle before their very eyes.

I want you to think about that. The whole crowd that’s now assembling and getting larger and larger, a lot of them are there because they wanted to see Jesus and they wanted to see the miracle that Jesus did through Lazarus. So who’s the one that orchestrated the crowd on Palm Sunday? Jesus.

He’s orchestrating his own parade. He’s getting his donkey, he’s getting the crowd, he’s putting all of the pieces together and he’s doing it intentionally and strategically. Now I want you to think about Lazarus for a moment as well because it says the chief priests, they already have a death warrant on Jesus.

Now they’re gonna try to kill Lazarus as well. And what I love about the story of Lazarus is that I think the person that was most surprised that they were raised from the dead, wasn’t Mary and Martha, certainly wasn’t Jesus, may have been the disciples, but the person that was most surprised they got raised from the dead was who? Think about this, four days, you’re with God for four days. And then you open your eyes and you’re like, why am I back on this earth? Put me back in there.

No, like I would have been putting the wrap back around my body and I would have been hopping back into the thing. No, put the stone back. Why would I wanna come back to this earth full of conflict? Why would I wanna come back to this earth full of disease and hardship? And now this poor guy has people chasing him wanting to kill him.

Look at what he came back to. Which I think if it was me, I’d be like, I already know what it’s like on the other side. I’m over here, if you wanna kill me, I’ve already died once, might not just do this again.

But the purpose of doing this is so that people would believe that Jesus is who he says he is, he is the one true God. And he also does it because this was the crowd that was gathered on Palm Sunday. And so they go ahead of Jesus and they’re shouting.

They’re not just singing, they’re shouting these words out. Hosanna to the son of David. David, very key Old Testament figure.

He was the king of Israel. By the way, David rode a horse into Jerusalem. Blessed is he who comes in the name of the Lord.

Hosanna in the highest heaven. And you can’t have a Palm Sunday service without having a song or two that has the word Hosanna in it, amen? Like if the team just said, we’re not singing a Hosanna song, you guys would be really upset. As you should be.

And if you didn’t get a palm branch on your way in from an usher, you’d also be upset. You’d be like, get with the program, it’s Palm Sunday. You sing Hosanna and you get a palm branch.

And it’s the day that all of the artists in the church love because they can make crosses while I’m preaching. So all the ones with ADD and art skills. I mean, this is your jam.

This is your favorite service of the year, isn’t it? Here’s my question. What does Hosanna even mean? She knows how quiet it is in here. You ever think sometimes we sing things and we don’t really know what they mean? Close.

Someone just said it. It means save us. So now think of the song that you sing, Hosanna, Hosanna, Hosanna in the highest.

Save us, save us, save us in the highest. When these people are shouting Hosanna, what do they think Jesus, or what are they asking him to save them from? The governments, the Romans who had oppressed them. They’re saying words, but they aren’t actually saying the words that Jesus is going to accomplish on the cross.

They’re still looking at things from an earthly perspective. And even though they know he’s on a donkey and he’s not on a horse, in the back of their minds, they’re still hoping that Jesus is gonna overthrow the Roman government. And that once again, the Jewish people, the Israelites will have their own ruling body and they’ll go back to the days when King David ruled over them.

And so you can imagine just what must have been taking place on this first Palm Sunday. He enters into Jerusalem now, right? He’s going into the city and the whole place is stirred and people are asking, who is this? There were people that still didn’t know who Jesus was. There was people that still hadn’t heard the teachings of Jesus.

And some of them are answering, well, he’s from Nazareth in Galilee, but he’s a prophet. We know he’s a rabbi, we know he’s a good teacher, but there’s people that hadn’t put their faith in him up to this point. And of course, all throughout Jesus’s ministry, there were people that rejected him.

There was people that refused to believe that he was the son of God. And a lot of that opposition came from the religious leaders. And so part of the religious leaders were people called the Pharisees.

They are also in the crowd. They’re also watching this all unfold. They go right up to Jesus on the donkey and say, you need to rebuke these people.

You need to tell them to stop shouting these words out. You are not who you say you are. You are completely disrupting one of our most important festivals.

You gotta put an end to this. And Jesus being Jesus, which he’s really good, by the way, if you didn’t know that, he’s really good at firing back lines. You have people like that in your family, that they’re just really good at this stuff.

I mean, without a doubt, he says, I tell you that if they keep quiet, the stones will cry out. Which I want you to think about this. When he says these words to people that already hate him, that want him dead, and there’s a couple things going on in this passage when he says this.

One is when he’s saying these stones will cry out, that God has the ability to take an inanimate object and make it do something it’s not supposed to do. But in the original context, what he’s saying is, if they don’t cry out, I am the creator. I have the ability to create more children, more human beings, who will cry out to me and ask me to save them.

So now, when Jesus says these words to the religious leaders, do you think he was creating peace in their heart or more conflict in their heart? Conflict, these guys were angry, they were livid. Like, who do you think you are and how dare you talk to us this way? Again, every step of the way, he’s calling the shots, he’s ordering their steps. And I couldn’t help but think this week, in the society that we live in and all the challenges that we face, it just feels like we’re starting to enter into this realm where it feels like we’re kind of being told that we need to keep quiet.

Does anyone sense that maybe at your place of work? College kids that are in here, any of you sense that at your college campuses? Or even when it comes to being a follower of Jesus? You can believe in any other religion you want, you can sign up for any other club you want, but if you’re gonna believe in Jesus and you’re gonna believe the teachings of Jesus in the Bible, then you’re kind of just treated differently and you’re kind of an outcast. And it’s not any different now, like the way that people treated Jesus and the way that they approached Jesus and the way they challenged Jesus. And I just believe, church, that we have to get more bold in our faith.

I believe that we need to not be afraid to share the hope we have in Jesus, but we do it with gentleness and kindness. We extend that invite to Easter of the loaves that need to know the hope they can have in the one true and living God because their souls hang in the balance. It’s an eternal matter between this life and the next.

These Pharisees are very interesting because obviously they’re not very happy with Jesus and they’re talking amongst each other. And for some reason, this is one of my favorite verses because they say, look how the whole world has gone after Jesus. And really at this point, the whole world hadn’t gone after Jesus.

They’re just in Jerusalem, but for them, their whole world was Jerusalem. And these festivals were so important to them. Follow me here.

They wanted to do things the way that they had always done them. They wanted the sacrifices the way they were. They wanted the people that were in power in the religious institution with their priest and all the people that came with them.

And most importantly, they wanted to be able to control the people. Are you following me here? Isn’t that always the inclination where people that get placed in power, it feels like once they get to a certain level, they wanna be able to control the population. And so that’s their biggest frustration is their whole world was built on legalism.

They have gotten so far away from the things of God and Jesus now is challenging the foundation of what they had always known. So I wanna ask you this as well this morning, because here it is 2026, we’re at the end of March. So we’re three months into this new year.

How is your whole world going? Not the whole world out there, because we know that’s all messed up and everything going on on our planet. How about the world that you can control? The world that’s right in front of you. Is there conflict in your life? Are you fighting with your spouse? Is there dysfunction in your family? Are some of you stressing about what’s gonna happen this Easter and who’s gonna come and who’s not gonna come and whose house you’re gonna go to? And I got friends, that every year they like go on this like tour.

They should just get a tour bus and they gotta try to keep everybody happy and go to like six houses on Easter. I’m just like, that’s nuts. First of all, how much ham can you eat, you know? Or is there peace? Has God been good to you this year? As you look back in just the last few months and you can see the goodness of God and maybe not everything’s worked out the exact way that you want it to, but you can just have this sense of, man, God really is working in my life and God is ordering my steps and the more that I enter into the reality that no matter what happens, I know that he will work out his perfect plan, the more peace I seem to have in my heart, amen? So how about this? What if we narrow it down from what’s happening this year to how about this week? If you were to hand me your cell phone and I was to look at your Google calendar, is your week already completely full? Are some of you already overscheduled this week? And you’re like, man, I know, thank God, Shepherd’s Gate’s got 12 services in eight days, but I’m gonna have a hard time getting here for some of the services because I’m already overbooked and overplanned.

I ask you this, what would it look like to cancel some meetings and appointments this week? Would that really break you? What about this? What if you leave here today and you email your boss and you take a couple of days off this week? And you say, it’s Holy Week, Jesus loves you, love your favorite employee. P.S., join me for Easter services, we have five of them. Like so often I think we just arrive and it’s like, oh man, it’s Palm Sunday, oh man, it’s Holy Week, and we don’t actually think about the significance of this week in the life of the believer, and how maybe there’s an opportunity for us to actually slow down and to take a deep breath and to enter into the significance in the life of the church and the calendar year of what this actually means.

Now I’ll tell you what’s going on in my household. When Lisa and I first got married, we obviously were running separate tracks. My wife’s a hairdresser, and so she’s got her work and her clients, and being here at the church, you can imagine the two busiest times in the life of the church for a pastor is what? Christmas and Easter.

Christmas is actually easier because you just do the same service over and over again. Holy Week, Easter, you got all sorts of services that you gotta plan for. And what do you think is the busiest season in the life of a hairdresser? Anybody know? Wouldn’t you know? Hairdressers also are very busy at Christmas and Easter.

So let me just tell you this. Pastors shouldn’t marry hairdressers, and hairdressers shouldn’t marry pastors, okay? Since we have been married, and then we brought children into the world, and it just got all screwed up because now our kids are at different schools, and their spring breaks don’t line up, which is just really annoying. Can I just tell you that? You guys can all feel sorry for me.

Those of you that have kids at different schools, or your school teachers, and you know how this works, or your kids are at college, it just creates chaos, doesn’t it? And you’re trying to sort this all out and figure this all out. Well, when we first got married, actually, Lisa, because she was trying to fit all her clients in, because women really want their Christmas hair, and women really want their Easter hair. And so she missed several years in the beginnings of our marriage, Maundy Thursday services and Good Friday services here at Shepherd’s Gate.

I would come alone. And a few years ago, we kinda sat down and we kind of made the decision that we weren’t gonna live like that anymore. And I said, you’re probably gonna tick some ladies off.

And the ladies you’re gonna tick off are the ones that wait till the last minute to schedule their appointment. Lindsay’s nodding her head because Lindsay’s one of our worship leaders. She’s also a hairdresser, and you’re probably scheduled to sing at a bunch of our services, and you’re probably in the dilemma of, do I sing for Jesus, or do I make more money? Do I sing for Jesus, or do I make all these ladies happy and beautiful for their Easter pictures? The stress.

This is really a sermon about hairdressers now, just so you know. What we put these ladies through. But what would it be for you? Parents, imagine this.

What does it look like to send a text message to the coach for little Johnny or little Susie and say they’re not coming to practice or they’re not coming to rehearsal this week? That our family is gonna be participating in Holy Week. And again, this is the beautiful part about being followers of Jesus and understanding grace. None of this is a got-to.

The got-to was the system that was created at this time. This is how they got themselves in trouble and why the priests were so adamant that things had to be done a certain way. We are on the other side of grace.

We are saved by grace through faith. It’s not a work of ourselves so that nobody can boast. It is a free gift from God to us.

And so it’s not a have-to, it’s a get-to. We get to enter into this week. We get to pause our lives and slow down our lives long enough to take that deep breath and to get that rest and to let God fill our hearts and our lives.

Does that make sense? Because this is what it comes down to. Jesus did not come to save us from earthly enemies. His disciples weren’t gonna figure out this reality until after his death and resurrection.

He’s not fighting an earthly war. He didn’t overthrow the Roman government. He came to save us from the enemy of our souls by fighting a spiritual war that none of us could have ever fought on our own.

And when you see this whole idea of enemy of your souls, do you know who the enemy of your soul is? It’s three things. Three things that are vying for your soul. Number one is Satan.

He hates you. He wants to kill, steal, and destroy you, your marriage, and your family. Do you know the other enemy of your soul? Planet Earth and the culture that we live in and the distractions that constantly tell us, oh, you need more money or you need to do this or you need to do that or you need to be like this other family or you need to have your kid in this activity or that activity.

All of those things that constantly go against what it is that God has for us. And the third, and this is the hardest one, what’s the third one? It’s ourselves looking in the mirror because we’re so drawn to want to do things our way and to go our way or to shout out Hosanna and tell God, we want you to save us from these things, but we don’t want you to save us from these things. And yet, we need what only he provides and he only provides it through Jesus Christ, which is the salvation of our souls.

Because the longer we live and the more we do these Holy Week services, the closer we get to Jesus coming back in the clouds. By the way, he’s gonna be on a horse. King Jesus is coming back and we don’t know the day or the hour that he’s coming.

And in that moment, in the twinkling of an eye, that those who have faith in him are gonna be brought up into the clouds, into the sky, and we will be with Jesus forever and ever and ever. And here’s what’s so cool. Look at what’s gonna happen in that moment.

John tells us that he looked and there before him was a great multitude that no one could count, from every nation, tribe, people, and language, standing before the throne and before the Lamb of God. And they’re wearing white robes and they’re holding what? In their hands. And they are shouting Hosanna to the Son of David, Hosanna in the highest heavens, Hosanna, Hosanna, Hosanna.

And that’s our heart’s desire for you this Holy Week, is that God’ll take the conflict that’s in your life that he already knows. He knows every last detail that the conflict that you may be experiencing, and instead he wants to exchange that conflict with the peace that only he can give you this Holy Week. Amen.