The Significance of the Triumphal Entry
The Slowdown in Human History
Boy, it is good to be with you here this week for Home Church! If you have your Bibles, turn to the book of Matthew. We are going to jump back into our series and enjoy some time in Matthew as we head toward Easter. If you happen to be a guest with us, we at The Well Community Church have been in the book of Matthew now for a number of months, enjoying this slow plow through the text. In typical Well fashion, we are going to open up Matthew 20 and cover all the way through chapter 21, verse 11. That is our standard approach: we take the Bible and cruise through it verse by verse, asking two very significant questions. What did the Bible mean in its original context? And what does it mean for us in ours?
I want to extend a special welcome to those who have been journeying with us, and especially to those joining us for the first time. For many folks, church might be a brand-new thing. You may have logged on knowing that there is a church teaching the Bible where you can experience what Christians do. If that is you, we are so glad you are here. What you are going to hear today is about the remarkable nature of Jesus Christ—who He is and the power He has in our lives, not just at one point in time, but over time.
I also want to give a quick shout-out to my friends up at Hume Lake Christian Camps. To date, they have pulled off the best Home Church experience I have ever seen. They parked a box van on the side of a hill, projected onto it, rigged up sound, and basically created their own drive-in theater up at Hume Lake! Hats off to their creativity. If you are anywhere in the world and think you can top an outdoor drive-in up in the sequoias, take a picture and have at it.
As you turn to Matthew 20, let me introduce a helpful concept in Bible study methods. The Bible was written with road signs all throughout the text. When we learn to spot these road signs, they bring tremendous insight to what we are reading. There are cause-and-effect relationships, comparisons and contrasts, and repetition. God sovereignly inspired the authors, and as they wrote, they left breadcrumbs along the trail.
One of the most significant principles is what is called the “law of proportion.” The idea is that the amount of space dedicated to a specific subject highlights its importance. For instance, the book of Genesis has fifty chapters, and three-quarters of those chapters focus on just four men: Abraham, Isaac, Jacob, and Joseph. The entire creation account takes up about a chapter and a half, while the patriarchs receive dozens of chapters because they represent the focal point of the book. Or consider Song of Solomon: seven verses on attraction, seventeen on dating, fifteen on courtship, seventeen on the honeymoon, and twenty-eight on conflict! It is as if God sovereignly emphasizes the most critical moments.
When you apply the law of proportion to the Gospel of Matthew, chapters 1 through 20 cover approximately thirty years, while chapters 21 through 28 cover just nine days. Matthew wants you to understand the supreme significance of these final chapters because that is where the treasure is. Matthew 1 through 20 moves like a movie with jump cuts: the birth of Jesus, thirty years later His ministry begins, six months later He does this, a year later He does that. But when you hit chapter 21, everything shifts into slow motion. The author slows the pace so we can gaze upon the true hero of the story—Jesus—and what He accomplished.
Beginning in chapter 20, Jesus moves methodically, intentionally, and systematically toward the crescendo of human history: the cross.
The Upside-Down Kingdom and the Final Miracle
Throughout Matthew, Jesus has been describing His kingdom. But His kingdom is completely different from anything this world has ever seen. It is an upside-down kingdom where if you want to find your life, you must lose it; where the first will be last, and the last will be first; where the greatest is the least, and the least is the greatest; where if you humble yourself, you will be exalted, but if you exalt yourself, you will be humbled.
Jesus has been traveling around the Galilee proclaiming this kingdom, taking occasional trips down to Jerusalem. But right here, a major pivot occurs. Jesus begins to move deliberately toward the cross.
He had already called His shot earlier in Matthew 20.
Matthew 20:18-19 (NASB)
‘Behold, we are going up to Jerusalem; and the Son of Man will be delivered to the chief priests and scribes, and they will condemn Him to death, and will hand Him over to the Gentiles to mock and scourge and crucify [Him], and on the third day He will be raised up.’
Jesus made it clear that crucifixion was coming. He was preparing to do what no one expected the King to do: die on a Roman cross.
As we come to the end of chapter 20, the stage is set and the anticipation is thick. Crowds have gathered, debating who Jesus really is. Is He a prophet? A teacher? A religious figure? Or could He be the Savior of the world? Before entering Jerusalem, Jesus performs one final miracle that places a divine stamp of authenticity on His identity.
Matthew 20:29-34 (NASB)
As they were leaving Jericho, a large crowd followed Him. And two blind men sitting by the road, hearing that Jesus was passing by, cried out, ‘Lord, have mercy on us, Son of David!’ The crowd sternly told them to be quiet, but they cried out all the more, ‘Lord, Son of David, have mercy on us!’ And Jesus stopped and called them, and said, ‘What do you want Me to do for you?’ They said to Him, ‘Lord, [we want] our eyes to be opened.’ Moved with compassion, Jesus touched their eyes; and immediately they regained their sight and followed Him.
Several details in this account are remarkable. First, these blind men call Jesus the “Son of David.” That is an explicitly messianic title. In 2 Samuel 7, King David was given a covenant promise that one of his descendants would rule on an eternal throne. These men also address Him as “Lord,” a title of reverence and complete submission. Even though the crowd sternly tells them to be quiet, they cry out all the more.
When Jesus stops and calls them over, verse 34 tells us He was moved with compassion—a deep, visceral emotion that moved Him to action. He touched their eyes, and immediately their sight was restored.
In doing this, Jesus authenticated His divine mission. Back in Luke 4, when Jesus began His public ministry in the synagogue at Nazareth, He quoted from Isaiah 61, declaring that the Spirit of the Lord had anointed Him to proclaim sight to the blind and freedom to the oppressed.
Luke 4:18-19 (NASB)
‘THE SPIRIT OF THE LORD IS UPON ME, BECAUSE HE ANOINTED ME TO PREACH THE GOSPEL TO THE POOR. HE HAS SENT ME TO PROCLAIM RELEASE TO THE CAPTIVES, AND RECOVERY OF SIGHT TO THE BLIND, TO SET FREE THOSE WHO ARE OPPRESSED, TO PROCLAIM THE FAVORABLE YEAR OF THE LORD.’
By healing these blind men, Jesus proved He was not just a teacher from Nazareth. He demonstrated that He is indeed the promised Savior sent from God.
The Presentation of the King
Having performed this final sign, Jesus prepares to enter Jerusalem in what is traditionally called the Triumphal Entry.
When we read about the Triumphal Entry, it is worth contrasting it with the Second Coming described in Revelation 19. When Jesus returns in Revelation 19, He rides a white horse, a sharp sword proceeds from His mouth, and the saints follow Him robed in white while He judges the nations. That future return is undeniably triumphant in power and majesty.
Here in Matthew 21, however, Jesus presents Himself as King in a profoundly humble manner. He echoes a Roman triumphal procession—the ticker-tape parade rolled out for a returning general or Caesar—yet He does so in a way that reflects His upside-down kingdom.
This event is recorded in all four Gospels. Mark gives it to us in his fast-paced, staccato style. Luke provides the historical nuance and backstory. John notes in John 12:16 that the disciples did not understand what was happening at first; only after Jesus was glorified did the light bulbs turn on. Matthew presents the scene with specific focus on prophetic fulfillment.
Matthew 21:1-3 (NASB)
When they had approached Jerusalem and had come to Bethphage, at the Mount of Olives, then Jesus sent two disciples, saying to them, ’Go into the village opposite you, and immediately you will find a donkey tied [there] and a colt with her; untie them and bring them to Me. ’If anyone says anything to you, you shall say, ‘The Lord has need of them,’ and immediately he will send them.’
Notice how Jesus orchestrates every detail. He tells two disciples exactly where to go, what to find, and what to say. Throughout His ministry, whenever crowds tried to make Him king by force, Jesus slipped away, repeatedly stating that His hour had not yet come. But here in Matthew 21, the hour has finally arrived. He deliberately sets the stage.
Matthew 21:4-5 (NASB)
This took place to fulfill what was spoken through the prophet: ’SAY TO THE DAUGHTER OF ZION, ‘BEHOLD YOUR KING IS COMING TO YOU, GENTLE, AND MOUNTED ON A DONKEY, EVEN ON A COLT, THE FOAL OF A BEAST OF BURDEN.’’
Jesus was not winging it. He was not improvising. He was intentionally fulfilling the prophecy of Zechariah 9:9. Matthew consistently points his readers back to the Old Testament Scriptures to show that Jesus fulfilled every expectation God had established.
Instead of entering on a warhorse or in an ornate chariot like a Roman conqueror, the King of the universe rides into Jerusalem on the foal of a donkey, embodying gentle humility.
Matthew 21:6-8 (NASB)
The disciples went and did just as Jesus had instructed them, and brought the donkey and the colt, and laid their coats on them; and He sat on the coats. Most of the crowd spread their coats in the road, and others were cutting branches from the trees and spreading them in the road.
The disciples placed their cloaks on the donkey, and Jesus sat upon them. As He traveled that one-mile stretch from Bethany and Bethphage across the Kidron Valley into Jerusalem, the crowds spread their garments and palm branches on the road.
In Deuteronomy 24, there is an interesting principle regarding pledges: if a person was too poor to offer collateral for a loan, they would offer their outer garment as a pledge of commitment. Some scholars suggest that laying garments on the road was an act by the common people pledging their allegiance and submission to Jesus as their King. Cutting palm branches and waving them was an established cultural expression of victory, celebration, and honor.
Save Us from What?
As Jesus rode toward the city, the atmosphere reached a fever pitch.
Matthew 21:9 (NASB)
The crowds going ahead of Him, and those who followed, were shouting, ‘Hosanna to the Son of David; BLESSED IS HE WHO COMES IN THE NAME OF THE LORD; Hosanna in the highest!’
The crowds shouted, “Hosanna to the Son of David!” The word Hosanna is an Aramaic expression that means “Save, I pray!” or “God save us!” They recognized His royal lineage and gave Him tremendous honor.
Yet Luke records the reaction of the religious leaders in that exact moment.
Luke 19:39-42 (NASB)
Some of the Pharisees in the crowd said to Him, ‘Teacher, rebuke Your disciples.’ But Jesus answered, ‘I tell you, if these become silent, the stones will cry out!’ When He approached [Jerusalem], He saw the city and wept over it, saying, ’If you had known in this day, even you, the things which make for peace! But now they have been hidden from your eyes.
When the Pharisees told Jesus to rebuke His disciples, Jesus answered that if they kept silent, the very stones would cry out. Then, looking over the Kidron Valley at the stunning view of the temple, Jesus wept over Jerusalem. He wept because He knew how fickle the crowds were, and how quickly their praise would turn.
When the people shouted, “God save us!” we have to ask: save them from what?
Depending on who you asked in the crowd that day, “save us” meant different things. For some, it meant save us from Roman oppression. For others, save us from poverty, or save us from our political circumstances. We often read our own theological understanding back into the text, knowing Jesus came to save us from our sins, but many in that crowd were looking for an earthly deliverer.
Matthew 21:10 (NASB)
When He had entered Jerusalem, all the city was stirred, saying, ‘Who is this?’
When Jesus entered Jerusalem, the whole city was stirred, asking, “Who is this?”
That question—Who is this?—is the single most important question you will ever answer.
I remember wrestling with that question myself. I came to faith in Jesus while I was in college. Before that, I had no clue who Jesus was. To me, Jesus was bundled together with the Easter bunny and Santa Claus. If you had asked me who He was, I would have said He was a good moral teacher who helped people and gave them someone to lean on. I had no idea He was the Savior of my soul.
It was not until college, when I truly heard the gospel, that I realized what was broken in me had nothing to do with my external environment and everything to do with my sin. I was born in iniquity and desperately needed a Savior. I needed God to save me—not from political leaders or economic struggles, but from my own sin.
Isaiah 53:6 (NASB)
All of us like sheep have gone astray, Each of us has turned to his own way; But the LORD has caused the iniquity of us all To fall on Him.
2 Corinthians 5:21 (NASB)
He made Him who knew no sin [to be] sin on our behalf, so that we might become the righteousness of God in Him.
That is the glory of the gospel. Jesus lived the perfect life we could never live, took our place on the cross, endured the wrath of God as our substitute, died for our sins, and rose victoriously on the third day.
Tragically, the crowd in Jerusalem began to cool almost immediately.
Matthew 21:11 (NASB)
And the crowds were saying, ‘This is the prophet Jesus, from Nazareth in Galilee.’
They had just shouted that He was the Son of David and the King who comes in the name of the Lord. Now they downplay Him: “This is the prophet, Jesus, from Nazareth in Galilee.”
Within just a few days, that same crowd would stand before Pilate in Matthew 27:22, not crying “Hosanna,” but screaming, “Crucify Him!” They completely missed who was standing right in front of them, fulfilling what the prophet Isaiah had warned.
Isaiah 6:9-10 (NASB)
He said, ’Go, and tell this people: ‘Keep on listening, but do not perceive; Keep on looking, but do not understand.’ ‘Render the hearts of this people insensitive, Their ears dull, And their eyes dim, Otherwise they might see with their eyes, Hear with their ears, Understand with their hearts, And return and be healed.’
Their eyes were dim, their ears were dull, and they failed to see the King who had come to redeem them.
Prophecy Fulfilled to the Very Day
What Jesus did during the Triumphal Entry was remarkable, but when He did it is equally astonishing.
Five hundred years before Jesus rode into Jerusalem, the prophet Daniel recorded an extraordinary timeline in Daniel 9. Daniel wrote that from the issuing of a decree to restore and rebuild Jerusalem until the coming of the Messiah, there would be a precise period of time: sixty-nine “weeks” of years, which equals 483 prophetic years, or 173,880 days.
We know historically and biblically from Nehemiah 2 that the decree to rebuild the walls of Jerusalem was issued by King Artaxerxes in the month of Nisan in 444 BC. If you start the clock at the issuing of that decree and count forward 173,880 days, you land precisely at the week of the Triumphal Entry in Matthew 21.
Sir Robert Anderson and other scholars have walked through the astronomical and historical math, demonstrating that the prophetic countdown ended on the exact day Jesus rode into Jerusalem on that colt.
Jesus did not accidentally stumble into fulfilling a five-hundred-year-old prophecy. Throughout His ministry, He avoided public coronation because the prophetic clock had not yet struck zero. But when the appointed day arrived, Jesus intentionally rode into the city to present Himself as the Messiah. There is zero chance in human history that anyone could fulfill such specific prophecies to the exact day—unless He is God in human flesh.
Jesus is not merely a good teacher. He is not just a prophet or a historical figure. He is the sovereign Savior of the world.
John 3:16 (NASB)
’For God so loved the world, that He gave His only begotten Son, that whoever believes in Him shall not perish, but have eternal life.
Trusting the Sovereign King
We serve a Savior who spans human history. By His grace and power, He orchestrated the events of history so that He could step into our world at the exact right moment, offer Himself as the perfect sacrifice for our sin, and defeat death through His resurrection.
As we approach Easter, I want to ask you: how do you answer that question in verse 10? Who is this?
My prayer is that your view of Jesus would be elevated and right-sized. I pray you would see Him high, lifted up, and exalted as the only one worthy of your complete trust.
I know we find ourselves in an unusual season right now. You might be watching Home Church on your couch in your pajamas, listening in your car, or running on a trail with earbuds in. Whatever your circumstances, remember this: the sovereign God who fulfilled a 500-year-old prophecy to the exact day is the same sovereign God who is fully capable of carrying you through whatever you face today.
Instead of placing your hope in circumstances or human leaders, place your trust in the King of kings. He spoke the universe into existence, created you in His image, pursued you in your brokenness, and died in your place on the cross so that through faith in Him, you might have eternal life.
Let’s pray together.
Father in heaven, it is with great delight and assurance that we come to You, knowing that You are good. Thank You for providing salvation through Jesus Christ. You have called us out of our sin and invited us into a relationship with You.
Lord Jesus, You are the Son of David. You are the promised King. You are the Savior of the world. Hosanna in the highest, for there is none like You! Remind us this week of Your absolute sovereignty. You presented Yourself as the sacrifice for our sin, You died on that cross, You were buried, and You rose from the grave to give us life. We worship and celebrate You as our King. In Jesus’ name, Amen.