Palm Sunday: Matthew 21:1-13 | The King & His Kingdom
Good morning, Main Street Church. It’s great to be with you today.
Before we dive into this Palm Sunday text in Matthew, I want to ask you a question: Have you ever been really, really excited about something, had it all built up in your head, the hype was through the roof, and then the reality just didn't live up to the expectation?
Maybe it’s a massive sporting event or a highly anticipated UFC fight. I remember the first time I ever bought a UFC fight: we had a bunch of friends over, it was Conor McGregor, a super hyped-up fight, and we were so excited. But just 10 seconds in, Conor gets kicked in the leg, breaks his leg, and the fight is over. We all just sat there, stunned: wait, what just happened? Is it over?
Or take movie trailers. They can look intense and action-packed; you can’t wait to see it. Then, you go to the theater on opening night, and it’s a completely different film—slower, confusing, and definitely not what you expected. You walk out thinking, “That’s not the movie I signed up for.”
Maybe it's ordering something online. I remember ordering the ring sitting on Megan’s finger over there—another story where the wait built anticipation. The ring arrived when Ryan and I were flying back from Ethiopia. I had been tracking the package for so long, anticipating it, and when I finally got back and opened it…. In my eyes, the ring was so small. I questioned everything for a moment. I was like, " What is this? " Not sure what I was expecting because it’s not a very small ring—Megan, you can show everyone after this—but I guess I was thinking, wow, all that waiting, money, expectations, and it's all just this small little ring in this little box.
All of those moments have one thing in common. The expectation didn’t match the reality. You thought you knew what was coming, but when it finally showed up, it looked completely different.
That is exactly what Matthew wants us to see in Matthew 21 on the day we call Palm Sunday: the expectations people had for a conquering king collided with the reality of Jesus as a humble Savior.
The people of Israel hadn't just been waiting for a few weeks; they had been waiting for a King for generations. They had been building their expectations for centuries, imagining exactly what He would be like, how He would dress, and, most importantly, who He would conquer. They thought they knew exactly what was coming. And then Jesus shows up.
He doesn't arrive on a powerful war horse. He doesn't come flanked by a private militia or a line of chariots. He shows up on a donkey. In that moment, the "hype" of a conquering King hit the reality of a humble Savior. Everything they expected about the King didn’t match the King who actually came.
Isaiah told us this would happen in Isaiah 53:
He had no beauty or majesty to attract us to him,
nothing in his appearance that we should desire him.
He was despised and rejected by mankind,
a man of suffering, and familiar with pain.
Like one from whom people hide their faces
He was despised, and we held him in low esteem.
(Isaiah 53:2-3)
Many of us know this story: the palm branches, the shouts of “Hosanna,” Jesus riding into Jerusalem. But have we stopped to ask: What does this actually mean?
Matthew tells us that when Jesus entered, the whole city was "stirred." That word means like an earthquake. The ground was literally and metaphorically shaking. And it makes sense: it was Passover week. People had traveled from all over the known world to be there. The city was packed, the air was thick with emotion, and the people were expectant.
Jesus chose this exact, high-pressure moment to reveal Himself publicly as King. This wasn't a random choice or an accidental timing. This was a deliberate declaration.
To understand the weight of this moment, look at how the Gospel writers handle it. Usually, a biography focuses on a person's life, but the Gospels are obsessed with Jesus' final week
Matthew spends about 25% of his book on this week.
Mark spends about 33% of his book on this week.
Luke spends about 20% of his book on this week.
John spends nearly 50% of his entire Gospel on these final seven days.
Over the next week, from now until Easter, Ryan, Demer, and I are all going to be talking about this King. We’re going to look at this story through the lens of Matthew, 1 John, and even Genesis to see why this moment matters so much.
But what is actually going on here, on Palm Sunday? Matthew is making a crucial point: he is showing us much more than a parade—he is revealing the core of his gospel. Matthew wants us to see the collision between what people expected from a king and the kingdom Jesus actually brings. This clash between the kingdoms of this world and the Kingdom of God is the main point of Palm Sunday.
The Kingdom People Expect
We are actually going to start with verses 6-11, it says
The disciples went and did as Jesus had directed them. They brought the donkey and the colt and put on them their cloaks, and he sat on them. Most of the crowd spread their cloaks on the road, and others cut branches from the trees and spread them on the road. And the crowds that went before him and that followed him were shouting, “Hosanna to the Son of David! Blessed is he who comes in the name of the Lord! Hosanna in the highest!” And when he entered Jerusalem, the whole city was stirred up, saying, “Who is this?” And the crowds said, “This is the prophet Jesus, from Nazareth of Galilee.”
(Matthew 21:6-11)
Jesus makes His way toward the city gates; the atmosphere in Jerusalem isn't just "busy", it’s electric. Matthew tells us the whole city was "stirred," like an earthquake.
And when you look at what the crowd is doing in verses 6 through 11, you realize this isn't just a spontaneous welcome party. These people are performing a very specific, very intentional set of rituals.
First, they start cutting down palm branches. To us, palm branches are just something kids wave in Sunday school, but in the first century, they were a powerful symbol of Jewish nationalism and military victory. They were essentially the ancient version of an Olympic gold medal or a national flag. They were waving them because they believed a winner had finally arrived.
Then, they begin spreading their cloaks on the ground. This was an ancient act of total submission to a king. By laying their clothes in the dirt for the donkey to walk on, they were saying, “Everything I have belongs to you. I am your subject.”
And then the noise starts. They begin to shout: “Hosanna to the Son of David.”
“Hosanna!” literally means, "Save us, we pray!" They are quoting Psalm 118:
“Save us, we pray, O LORD!
O LORD, we pray, give us success!
Blessed is he who comes in the name of the LORD!”
“Son of David!” was the ultimate title for the long-awaited Messiah. We see this in 2 Samuel 7:12-13:
When your days are fulfilled, and you lie down with your fathers, I will raise up your offspring after you, who shall come from your body, and I will establish his kingdom. He shall build a house for my name, and I will establish the throne of his kingdom forever.
The Jewish people knew this prophecy pointed to their savior.
So, as Jesus is riding into Jerusalem, this was not a random moment of worship. This was the coming of a King.
So, what exactly were they expecting? If you could have hopped into the mind of someone in that crowd, they weren't thinking about "going to heaven when they die." They were thinking about it right now. They were expecting a political ruler and a military leader.
Three hundred years earlier, Alexander the Great had entered this same city. He came in with a massive, terrifying display of power, and the people greeted him out of pure fear because he had crushed every other nation in his path. Now, the Jewish people see Jesus and think, "Finally, it’s our turn." They wanted a King like David, a warrior who would pick up a sword, kick the Roman occupiers out of their land, and restore Israel to its former glory.
For the people in the streets, this wasn't a church service; it was a political rally. You can hear the relief in their shouts!
“Finally, we’re going to be free!”
“Finally, someone is going to take care of those Romans!”
“Finally, everything is going to change for us!”
This is the uncomfortable truth: They weren’t wrong to want salvation. They were oppressed, hurting people who wanted justice. And honestly? Neither are we. We all want a "King" to come in and fix the things that make us feel small, broke, or out of control.
We want a king who fixes our finances…
“If I could just make a little more money, then I’d finally feel secure.”
We want a king who fixes our relationships…
“If they would just change, then everything would be okay.”
We want a king who fixes our stress…
“If life could just slow down for a minute, then I’d finally have peace.”
The problem is that we, just like that crowd, tend to define "salvation" as comfort, control, and our side winning.
We live in a world where people are often more passionate about their political party than they are about Jesus. We listen to the promises of the world that tell us, "If our candidate wins, you’ll have freedom; if the other side wins, the world will fall apart." We look for salvation in a ballot box or a bank account.
The crowd was right that they needed a Savior, but they were wrong about the kind of salvation they needed. They wanted a King to change their circumstances, but Jesus will tell them later this week.
Jesus answered, “My kingdom is not of this world. If my kingdom were of this world, my servants would have been fighting, that I might not be delivered over to the Jews. But my kingdom is not from the world.”
(John 18:36)
Jesus came to change their eternity. They wanted a victory over Rome; Jesus was looking past Rome to a much bigger enemy:
And you, who were dead in your trespasses and the uncircumcision of your flesh, God made alive together with him, having forgiven us all our trespasses, by canceling the record of debt that stood against us with its legal demands. This he set aside, nailing it to the cross. He disarmed the rulers and authorities[a] and put them to open shame, by triumphing over them in him.
(Colossians 2:13-15)
Jesus’ main concern was our hearts and the defeat of sin and death.
So the crowd thinks they understand exactly what kind of King this is... but Jesus is about to show them that they don't have a clue.
Which brings us to…
The Kingdom Jesus Brings
If you know the story of Jesus through the Gospel of Matthew, you might have noticed that Jesus is a walker, much like me. Not to brag.
He has trekked hundreds of miles through the dust of Galilee, along the shores of the Sea of Galilee, and through the hills of Judea. But here, as He reaches the final mile before the gates of Jerusalem, something significant changes. Jesus stops walking.
He pulls two of His disciples aside and gives them a highly specific mission: go into the village, find a donkey and her colt, untie them, and bring them to Me. If anyone asks what you’re doing, tell them, "The Lord has a need for them." This wasn't because Jesus was exhausted or because His feet were sore. Jesus was using His physical surroundings to make a huge point. That he is King.
To understand why this was so shocking to the people lining the streets, you have to understand the "transportation culture" of the ancient world. In the Roman Empire, if you were a person of high status, a governor, a general, or a King, you didn't walk, and you certainly didn't ride a donkey. You rode a horse.
But not just any horse. You rode the most impressive, powerful, and intimidating horse you could find. A horse was a machine of war; it was a symbol of military dominance, speed, and the ability to crush anyone in your path. When a Roman general returned from a successful campaign, he would lead a "Triumph", a massive parade where he sat high above the crowd on a stallion, flanked by soldiers and the spoils of war. It was designed to make the people feel the weight of his power.
Think of it in modern terms. We have Air Force One, armored motorcades, and massive military parades with tanks and fighter jet flyovers. These things are designed to say one thing: "I am in control, I am powerful, and you should be intimidated."
But Jesus makes a different choice.
He rejects the impressive horse. He rejects the tank. He rejects the symbols of worldly dominance. Instead, he chooses a donkey.
Matthew tells us exactly why Jesus did this in verses 4 and 5. He was fulfilling a prophecy written five hundred years earlier by the prophet Zechariah:
Behold, your king is coming to you;
righteous and having salvation is he,
humble and mounted on a donkey,
on a colt, the foal of a donkey
(Zechariah 9:9)
By choosing a donkey, he was claiming the title of King while simultaneously redefining what a King looks like. A donkey is not an impressive animal used in battle. It’s a work animal. It’s what a farmer used to pull a plow or what a commoner used to carry luggage. It is a symbol of meekness, humility, and peace.
You don’t ride a donkey into a battlefield. You don’t use a donkey to lead a charge against a Roman legion. By riding that colt, Jesus was signaling to every person in that crowd: "Yes, I am the King you’ve been waiting for, but I am not the King you were expecting."
This is like if the president of the United States were to ride up to a press conference in something other than “The Beast”. Did you guys know about this? The Beast is the nickname for the U.S. President's heavily armored, custom-built Cadillac limo. This current version was made in 2018, costs about $1.5 million, weighs 20,000 lbs, features 8-inch armor, 5-inch bulletproof glass, run-flat tires, and a sealed cabin to protect against biological/chemical attacks. It carries the President's blood type, emergency oxygen, and advanced communications. One of, if not the most impressive car in the world. Instead of riding in on that, Jesus riding in on a donkey would be the president riding in on a Honda Civic. Nothing wrong with a Honda Civic, but it is definitely not the beast.
This is Jesus’ Upside-Down Kingdom.
Jesus wasn't just bringing a different "style" of leadership; He was announcing a completely different kind of Kingdom.
The world says power looks like force and control.
Jesus says power looks like humility and sacrifice.
The world says greatness is about winning and being served.
Jesus says greatness is about losing your life and serving others.
This isn't just a minor tweak to the system; this is completely upside down. It went against every instinct the Jewish people had. They were hurting, they were taxed into poverty, and they were living under the rule of Rome. They wanted a King who would pick up a sword and settle the score. They wanted a political revolution that would put them on top for once.
But Jesus saw a much bigger problem. He knew that if He simply overthrew Rome, the human heart would still be captive to a much greater ruler. He wasn't interested in a temporary political fix that would just need to be redone in another hundred years. He was interested in an eternal rescue.
Here is the big truth of Palm Sunday: Jesus didn’t come to take an earthly throne; He came to take a cross. We see in Mark 10:45:
“For even the Son of Man came not to be served but to serve, and to give his life as a ransom for many.”
(Mark 10:45)
The crowd was shouting for freedom from Rome, but Jesus was riding toward freedom from sin and death. They wanted Him to kill their enemies; He came to die for His enemies. They wanted a King who would rule over the nations; He came as a King who would give His life as a ransom for the nations.
We do the same thing today, don't we?
We treat Jesus less like a King and more like a customer support line.
“Hey, Jesus, I’ve got an issue over here. Can you fix this real quick?”
And the moment He starts addressing something deeper in us, we’re like, “No, no, no… not that. Just fix the situation.
We say things like…
“Jesus, just help me get through this test… this game… this week…”
“Jesus, fix this situation at work…”
“Jesus, make this relationship easier…”
But rarely do we stop and say…
“Jesus, change me.”
“Jesus, lead me.”
“Jesus, I’ll follow You wherever You go.”
But Jesus points us to a different Kingdom, one that cannot be shaken by an election or a revolution. He lifts our eyes past the temporary things of this world to a Kingdom of humility, gentleness, and hope. He came to solve a problem that a president, a king, or our circumstances could never touch: our separation from God.
If there was any confusion left about what kind of King Jesus is... He was about to clear it up immediately.
The Kingdom We Must Choose
If you were part of the crowd that day, you might have expected the "Triumphal Entry" to lead directly to a palace. You’d expect the King to go straight to the seat of government, demand an audience with the Roman authorities, and begin the process of political takeover. But Jesus doesn’t go to the palace. He doesn't go to the governor's mansion. He goes to the Temple.
And instead of a celebration, we see a confrontation.
Many of us have a mental image of "Gentle Jesus, meek and mild", the Jesus of the donkey. But as soon as He steps into the Temple courts, we see a different side of His character. He starts flipping tables. He’s driving out the buyers and sellers, scattering coins across the floor, and knocking over the chairs of those selling doves.
Why the sudden shift? Why did the Gentle King become so seemingly "ungentle"?
Well, during Passover, the city was flooded with people from all over the world. These people came with one goal: to meet with God and offer a sacrifice. But the religious system had turned an opportunity of worship into a "den of thieves."
There were two main ways people were being cheated:
The Sacrifice Scam: You would bring a dove or a lamb for sacrifice, but the Temple inspectors would declare it "unworthy." Then, conveniently, they had "pre-approved" animals for sale, at a massive markup.
The Temple Tax: You had to pay the tax in specific Temple currency. The money changers were there to help you exchange your "foreign" coins, but they charged dishonest, predatory rates.
The Temple was supposed to be a place where anyone, regardless of their status or wealth, could come into the presence of God. Instead, it had become a barrier.
I think of it like this. Many people bring coffee to church. Imagine if we at Main Street Church had people at the door checking your coffee cups. It’s a rule that you can’t bring any coffee in, but lucky for you, we have coffee here! It’s really good, holy, church coffee, and you can get an 8-oz cup for just $15! What a steal!
This is what made Jesus angry. Jesus is gentle, but He is not weak. He cares deeply about people having access to the Father, and when religious systems get in the way of that, He will flip the tables.
He said to them, “It is written, ‘My house shall be called a house of prayer,’ but you make it a den of robbers.”
(Matthew 21:13)
He is quoting Isaiah 56:7:
“My house shall be called a house of prayer for all peoples.”
(Isaiah 56:7)
That phrase: "My house." At this moment, Jesus is claiming ownership. He is equating Himself with God. He is saying, "You are messing with my Father's house, and you are messing with Me." The King is not just here to be celebrated with palm branches; He is here to rule and restore. He isn't just confronting external corruption; He is confronting anything, even "religious" things, that keep people from God.
Palm Sunday, which celebrates Jesus and marks the kickoff of Easter week, is also highly relevant to us today. Because, if we’re being honest, we aren't that different from the crowd in Jerusalem. We are still looking for salvation outside of Jesus.
We look for salvation in:
Politics and Leaders
Systems and Cultural Movements
Personal Control: We think that if we can just get our circumstances, our kids, or our careers to line up, we’ll be okay.
Let’s be clear: It is okay to care about these things. It is good to be passionate about justice and politics. There are people in this church right now who vote differently than you do, and that’s okay; we are all one family in Jesus. But the danger comes when we make those things ultimate.
We often talk more about political and personal kingdoms than we do about the Kingdom of God.
The Jewish people thought Rome was their biggest problem. They thought the Roman soldiers were the thing they needed to be "saved" from. But Jesus knew their greatest problem was the same as ours: sin and death. A new governor wouldn't fix that. A political revolution wouldn't fix that. Only a King on a cross could fix that.
You cannot read the account of Palm Sunday and stay neutral. This story forces a question that every one of us has to answer: Which kingdom are you actually living for? Are you living for the kingdom you want, the one of comfort, control, and earthly "wins"? Or are you living for the Kingdom Jesus brings, the one of humility, sacrifice, and eternal hope?
Jesus is not just a good teacher to be studied or a cultural symbol to be admired once a year. He is the King. And He is not a King who just wants your attention for an hour on Sunday morning. He is a King who wants your allegiance every day of the week. He wants to be the one who sits on the throne of your heart, directing your life, your money, your relationships, and your hope.
This week, as we move toward the cross and the empty tomb, may we stop waving branches long enough to ask ourselves: "Is He truly my King, or just my political candidate or selfish wants?"
Luke 9:23 says:
“If anyone would come after me, let him deny himself and take up his cross daily and follow me.”
(Luke 9:23)
Are you following Jesus for the convenience and for your get out of hell free card? Or are you truly taking up your cross daily and following him with your entire life?
The King We Didn’t Expect, but the One We Need
As we close today, I want you to think back to how shockingly small the ring I got Megan was, or that movie trailer that promised an action blockbuster but delivered a slow-burning drama.
We can laugh at those moments because the gap between what we expected and what we received was so massive. But as we stand here on Palm Sunday, we realize that this isn't just a funny story about misplaced expectations; it is the tension of the Gospel.
Two thousand years ago, Jerusalem was a city fueled by the hype of a political revolution.
Actually, before we go any further, we want to help you feel a little bit of that moment. Our elementary kids have been learning about this story, and they made some palm branches this morning. So I’m going to invite them to come up and wave those as they walk in, just like the crowd did when Jesus entered Jerusalem.”
(Children come and fill the auditorium, waving palm branches!)
Man, I love that. That’s the scene. That’s the excitement. That’s the kind of celebration that filled the streets that day.
They had their palm branches ready, the first-century equivalent of a foam finger or a campaign sign, because they were certain the King had finally arrived to crush Rome. They were looking for a King who would match their version of "salvation": comfort, political dominance, and their side finally winning. That was what the Kingdom People Expected. They wanted a ruler who would take the throne, but they were met with a Savior riding toward a cross.
Jesus didn’t show up on a stallion of war; He arrived on a borrowed donkey. This was the Kingdom Jesus Brought, a kingdom that subverts everything the world tells us about power. In our world, power is about how many people you can control; in Jesus’ Kingdom, power is about how many people you can serve. We spent our lives looking for a King riding on a horse who would destroy our earthly enemies, while Jesus was looking past the Roman soldiers to the true enemies of our souls: sin and death. He didn't come to take a throne through force; He came to take a cross through love. He knew that a change in government wouldn't fix the human heart, so He came to offer a change in eternity.
And if we thought this King was just a "gentle teacher" who wouldn't make any demands of us, He cleared that up the moment He walked into the Temple. In The Kingdom We Must Choose, we see that Jesus isn't interested in being a mascot for our political rallies or a lucky charm for our personal success. He is the Righteous King who flips the tables of our hearts. He confronts the "den of thieves" we build when we trade true worship for religious performance or earthly security. He isn't just asking for your "Hosanna" on a Sunday morning; He is asking for your allegiance for the rest of your life!
So, Main Street, here is the challenge for us as we enter Holy Week. Don't let this be just another "movie trailer" version of Jesus, the one where you cheer for the highlights but walk away when the story gets difficult.
The crowd shouted "Hosanna", "Save us, we pray!” and they were absolutely right to cry it out. They just didn't realize that the King they were cheering for was on His way to die for them.
“The same crowd that shouted ‘Hosanna’… days later shouted ‘Crucify Him,” which means it’s possible to celebrate Jesus… and still not belong to Him.”
The first time Jesus came, he rode into town on a donkey to bring peace.
The next time, he will ride in on a white horse to bring justice.
Is the question not whether we celebrate him?
The question is, do you belong to him?
Which kingdom are you truly living for? The one where Jesus fixes your circumstances, or the one where Jesus rules your life? This week, don't just wave a branch. Lay down your "cloaks", your pride, your political identities, your need for control, and submit to the King who is gentle enough to ride a donkey, but powerful enough to conquer the grave.
Response Questions:
Where in your life are you asking Jesus to fix your circumstances, instead of surrendering to Him as King?
If Jesus is truly your King, what would it look like this week to actually follow Him, not just celebrate Him?
