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Matthew 21:1-11 | The Triumphal Entry of Christ
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Welcome to week one of our brand new series: Entry & End Times. Over the coming weeks, we will walk through Matthew chapters 21-25, marveling at the final acts of Jesus in the last week of his earthly ministry before he departed this world. We will also be awakened by the words of Christ about what is coming for the world in the end times.
Our text today comes from Matthew 21:1-11—a passage that records the very first significant event in what we call the Passion Week of the Lord Jesus Christ.
In our human experience, no one knows the day or the hour they will depart from this life. However, there are circumstances when a doctor may tell a terminally ill person they have a certain set amount of time to live.
Consider this: if a person knew exactly when they would die, how much more significant would their final words and final actions become?
Enter the Lord Jesus Christ. He knew exactly when he was going to die. He knew exactly where he was going to die. He knew exactly how he was going to die. And he knew when he would return to the Father.
The year is AD 33. The place is the holy city of Jerusalem. The month is Nissan on the Jewish calendar—April in our terms. Jerusalem is crowded with 2 million people gathered for Passover, the biggest festival on the Jewish calendar.
At Passover, the Jews commemorated their great deliverance from 400 years of Egyptian slavery. History tells us that during this week, approximately 250,000 lambs were slain—one lamb for every family. This would give us over 2 million people packed into the city of Jerusalem.
Every year at Passover, they would slay lambs and spill their blood to remember the time they were delivered from Egyptian slavery. The blood on the doorpost symbolized the coming of Christ.
Matthew records the beginning of the public life's end for the Lord Jesus Christ. In Matthew 21, beginning in verse 1:
Now when they drew near to Jerusalem and came to the town called Bethphage, to the Mount of Olives, then Jesus sent two disciples, saying to them, "Go into the village in front of you, and immediately you will find a donkey tied and a colt with her. Untie them and bring them to me. If anyone says anything to you, you shall say, 'The Lord needs them,' and he will send them at once."
Jesus and his followers had walked approximately 100 miles from northern Israel near Capernaum, Caesarea Philippi, and Galilee all the way down to the south to Jerusalem. They had stopped every night for rest along the way.
On his journey, Jesus had stopped in the city of Jericho, where he won to the faith a rich man called Zacchaeus, who gave away half his goods. He had also stopped at Bethany, where he spent time with friends—Mary, Martha, and Lazarus, whom he had raised from the dead.
But when Jesus arrives at Bethphage, a suburb of Jerusalem near the end of his journey, he does something remarkable: he asks for a donkey.
Here is what strikes me: we have no record of Jesus ever riding an animal anywhere in the scriptures before this moment. He is not tired. He is not weary. He is not unable to walk the last mile.
What Jesus does is arrange a public display. He sits on that donkey so that everyone around him—the crowds that have been following him for miles—will see this man riding into Jerusalem.
This is intentional.
Up until this point, the Lord, though famous, had done nothing to draw unnecessary attention to himself. He had been operating quietly. But now, why would he pull off an elaborate stunt to draw attention to himself in front of 2 million people?
Matthew tells us why in verse 4:
This took place to fulfill what was spoken by the prophet, saying, "Say to the daughter of Zion, 'Behold, your king is coming to you, humble and mounted on a donkey, on a colt, the foal of a beast of burden.'"
Matthew, looking back in hindsight, remembers that Jesus arranged this elaborate entry because he was fulfilling a prophecy.
That prophecy came from a man named Zechariah, who lived 500 years before Christ was born. Five centuries before Jesus walked the earth, Zechariah wrote that a day was coming when the Son of God would roll into the city of Jerusalem sitting on a donkey.
But the prophecies didn't stop there.
In Daniel chapter 9, there is another prophecy about "seventy weeks." A man took it upon himself to do the mathematics—to calculate those seventy weeks in terms of years. According to that prophecy, when a king named Artaxerxes declared the rebuilding of Jerusalem, 483 years from that decree, the Son of God—the Prince, the Anointed One—would enter the city in the month of Nissan.
And according to history, exactly 483 years to the month and day, Jesus rode into the city of Jerusalem on this donkey.
The Lord arranged this public display to make sure the word of God does not fall to the floor.
When I read this text, three things stick in my heart.
God looks after his word to make sure it is properly performed.
You want to talk to me about other religious books? They have never said anything about the future. We have the only religious writing in the history of the world that contains hundreds of prophecies that have been accurately fulfilled. And Christ is the only human in history to fulfill these prophecies.
This reminds me that when God speaks, he watches over his word through history to make sure it does not fall to the floor.
That may not mean anything to you, but it means something to me. It reminds me that everything God has spoken over me, everything God has spoken over you, God will watch over his word to make sure everything he spoke will come to pass.
When he tells me my name is written in the Lamb's Book of Life, I don't have to be afraid of death. I have confidence in what God has said to me.
When you have received a word from God through a credible source, you can have confidence that the Lord will watch over that word to perform it. It doesn't matter how much time elapses between declaration and manifestation. God will watch over his word.
Let me share a testimony. My wife Lena and I had been saved for about two years. We were sitting in a church in North Carolina on the front row. Our son Malachi was 6 months old.
A prophet visited the church that day. She looked down at Lena sitting on the front row and said: "This child right here—bring him to me."
We went up with the child. She took Malachi in her arms and said: "This child, 6 months old, will be musically inclined. He will be musically gifted. He will write songs, and he will sway people into the kingdom of God."
Lena and I took that prophecy and hid it in our heart. We said nothing to anyone. We said nothing to the child.
Twelve years old: Malachi, in the computer in the kitchen, stumbles onto an app called GarageBand. He started making music. He made his first beat. He made worship tracks. He picked up a guitar and played it. He picked up a bass and played it. He picked up a piano and played it. He picked up drums and played it. Now he's singing all of it.
Now he's 20 and walking in the manifestation of what God spoke over his life.
Why? Because God watches over his word to perform it.
This is for everyone who God has spoken to about something that's still sitting in your heart. You buried it somewhere in a journal. You knew it was credible. You knew it in your heart. You're wondering, "God, when will this happen in my life?"
I'm telling you: as long as you are obedient and faithful, the Lord will not allow his word over you to fall to the floor.
It's going to happen in Jesus' name. It's going to happen.
This text also reminds me that the Lord aligned himself with the will of God. He knew about the prophecy, so he hopped on the donkey.
What a lesson for you and me: we are wise when we know the will of God and we align our lives with the will of God.
Jesus shows us the power of what happens when we read and submit, when we hear and submit, when we have revelation and submit. We live in such a way that we align ourselves with the word of God.
The Lord tells the disciples: "Go get that donkey."
John 12 tells us the disciples did not understand this command. They didn't understand why he wanted this animal. But the Lord knew the significance.
Here's what strikes me: you never know the weight of one singular act of obedience. You have no idea what's on the other side of a singular instruction from God.
God can speak to you from his word. He can speak to you from the Holy Spirit. And some of us love to disobey. You have no idea what we forfeit when we don't obey the instructions from the Lord. You have no idea what's on the other side of a clear instruction from God.
Move to a city. Move to a certain church. Take a certain job. Don't marry this person. Sign that contract. You have no idea what's on the other side of a single instruction from God.
That's why, if we are wise, we obey when God speaks.
And this is for parents: we are wise when we train our children to obey when God speaks. You have no idea what's on the other side of a singular act of obedience.
How did the disciples respond? The scripture tells us they were confused. But look at verse 6:
The disciples went and did as Jesus had directed them.
They obeyed in their confusion. They didn't understand why he was telling them to do this. They didn't know why he was telling them to leave the job, get out of that bad relationship, move to Atlanta, join the church. But they obeyed.
You don't need all the answers to be obedient. You just need submission and faith.
Start the business. Write the book. Move to the city. Take the job. Start the podcast. Just obey, even if you don't understand.
The Lord told me to change the name of our church. I didn't understand that. He told me to preach through Matthew. I didn't understand that. He told me not to preach with outlines. I didn't understand that. I'm just obeying.
Verse 7 tells us:
They brought the donkey and the colt, and put their cloaks on them, and he sat on them.
Another writer tells us that this donkey had never been ridden. If you know anything about donkeys, they are wild animals. Yet Jesus rode this child of a wild animal with the mother in front of it. Why? Because he's God. He tamed the animal because he created it.
Verse 8:
Most of the crowds spread their cloaks on the road, and others cut down 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 the one who comes in the name of the Lord! Hosanna in the highest!"
I want you to see what happens here. People take their cloaks—their jackets—and throw them down on the road for him to pass over.
Now, this is not 2025 in America. This is AD 33 in Israel.
The average person owned only one garment. Clothing was hard to come by. Only wealthy people had extra clothes. The average person did not have a closet full of clothes. Whatever they had on their back was all they owned.
But when these people see Christ, they take the most valuable thing they have off their back and throw it down on the floor. They said Christ was so worthy that there was nothing they had that they would withhold from him.
Yet some of you are stingy with your 25 cents in an offering. You want to keep back obedience. You want to keep back faithfulness. These people took the most valuable thing they had and threw it down, and they didn't even know if they would get it back.
Christ was that valuable to them.
They shout: "Hosanna to the Son of David."
"Hosanna" is a compound Hebrew word that means "God, save us now." It comes from Psalm 118. They are crying, "God, save us! God, save us!"
This crowd outside the city recognizes Christ as the Messiah. And when they see him, they are not asking for stuff. They are asking for salvation. They are asking for the intangible things that are more important than material possessions.
"God, give me wisdom. God, give me strength. God, give me revelation. God, save my soul."
Here's what strikes me: this crowd outside the city is shouting, "God, save us." But just a few days later, another crowd will say, "Crucify him."
I want to point this out to you: be careful not to live in the praises of people. The same people who love you one week will hate you the next week.
If you have to find your affirmation from the praise of people, you will be weak, and you will be in trouble. If you live by their praise, you will die by their rejection.
That's why we must get our affirmation from above.
Thank God for praise. Appreciate when people say you did a good job. Praise God for that. But if your affirmation is only horizontal, you are in trouble.
You better know how to hear praise and say thank you, and hear rejection and say God praise them anyway. You better know how to find your affirmation from above.
Although these are two different crowds, if you read the text carefully, if any of the people shouting "Hosanna" wanted Jesus to defeat the Roman Empire, they were mistaken.
He's riding a donkey. A donkey was a symbol of peace. Warriors rode horses.
Jesus is telling them: I'm not coming as a warrior king first. I'm coming as a king of peace.
But the next time he comes on an animal, it will be on a horse. The next time he comes, he's not coming to make peace. The next time he comes, he's coming to make war.
You better know what side of that battle you're on.
Verse 10:
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."
When Jesus rolled into the city of Jerusalem, the whole city is in an uproar. Their hearts are stirred. Another translation says their hearts are moved. Another says there's pandemonium in the city. They're confused. "Who is he?"
But here's what breaks my heart: John tells us that when Jesus approached the city, he wept. Why? He was weeping because he knew a lot of them would reject him and die in their sins, eternally separated from God.
The Lord is crying as he rides into the city.
I want to say to us as a church: I would to God we would shed those tears. I would to God we would feel what he felt.
I would to God we would drive through Atlanta, we would hop on social media, we would see what's happening all across our country and all across our world, and we would shed the same tears that the Lord shed.
I would to God we would feel the pain that he felt. That we would see the lost, see the broken, see those who are going to reject him, and it would move us to tears. It would move us to pray. It would move us to be generous. It would move us to be serious about the spread of the Gospel.
Time is running out.
I'm preaching to you about a King who came in the year AD 33, and I'm talking to you about a King who's about to come very, very soon. We don't have much time left.
If there's anything we need right now, it is an awakening in our soul, an awakening in America, an awakening around the world: Christ is coming.
My prayer for us is that we would shed the same tears he shed. That our eyes would be open. That we would do everything we can to push the gospel, to get Christ as close to as many people as possible, while still shedding tears for those who are far away.
This is what the scriptures call the triumphant entry of Christ. This is the first event in what will be the final week of his earthly ministry.
And on the heels of that, we will hear his powerful words about what is coming for everybody in this country and around the world in these end times.
This is a series for you to pray over. Pray that God would spread it as far and wide as possible, that men will understand: Christ is coming.
And he ain't coming on no donkey this time. He's coming to make judgment and war.
We pray that people will be on the right side of that battle, and that we as a church would get out of our foolishness and rally together for the glorious spread of the Gospel of our soon-coming King.
Eternal God, wise Father, we feel your spirit right now. We know that your Son is coming, and his second coming will not be on a donkey.
Lord God, we pray you would awaken America. Awaken the nations of the world. Jesus, let them know the Messiah is coming, that he's going to rule from the city of Jerusalem, and that time is running out.
I pray for revival to break out in this nation, Lord—to break out in cities all across America and around the world. I pray their hearts will be stirred as Christ comes near them.
And Lord, we as a church, help us to do all we can to spread this gospel. Help us to see the beauty of biblical prophecy and how you keep your word to your children.
Let us marvel over Christ. Let us marvel over his powerful, public entry into the city for the last time. And be reminded: he's coming to do it one more time.
May we be found faithful when he rides in the second time—whatever day that is. It could be next week, next month, next year. May we be found faithful when he rides in the second time.
I pray this over us in the mighty, majestic, and matchless name of our Lord and Savior Jesus Christ.
Amen and amen and amen.
