A Most Beautiful Entrance

Palm Sunday - April 13, 2025

INTRODUCTION

Good morning! Welcome to City on a Hill Community Church and welcome to Palm Sunday. The Sunday before Easter, often referred to as Palm Sunday is in recognition of Jesus’ triumphal entry into the city of Jerusalem.

Now, if you’ve been following along with us, we have been making our way through Luke’s gospel for 18 months now. And during our journey through the gospel, Jesus has been slowly making His way towards the city of Jerusalem where He will time His ministerial journey in such a way as to enter Jerusalem six days before Passover.

And Palm Sunday celebrates that entrance into the city. And it is a beautiful scene where the crowds are praising His name. They’re shouting Hosanna! They are proclaiming Him to be the prophesied Son of David, the Messiah of God. And so it really becomes quite shocking when we see such a triumphant entrance quickly turn sour over the course of a few days where He would be arrested, beaten, mocked, ridiculed, and ultimately crucified on the cross.

But I won’t jump ahead into the Good Friday message. You will need to come back this Friday at 6pm to hear that passage told through music. What we will focus on today is the entrance of Jesus into Jerusalem. And this passage and this Palm Sunday message is told each year at this time. But it is always good for us to receive God’s Word and to hear it preached. After all, Paul writes, “So faith comes through hearing, and hearing through the word of Christ” (Romans 10:17). So while the passage may ring familiar to many of you this morning, we hold fast to the words of Hebrews 4:12 — “For the word of God is living and active, sharper than any two-edged sword, piercing to the division of soul and of spirit, of joints and of marrow, and discerning the thoughts and intentions of the heart.”

This morning, we will read the account of Jesus’ Triumphal entry from the perspective of the disciple Matthew. And in his account we will come to see that this passage is all about “identifying markers”—these glimpses or evidences that point to the identity of Jesus as the Christ, the Messiah.

There are a lot of crime television shows, true crime podcasts and documentaries today. It is a very popular genre in our culture at the moment. And if you have ever found yourself watching such shows or listening to such podcasts, you likely understand how a lot of crimes are solved. There is the gathering of evidence and thanks to advancements in technology, there are many ways of doing that today. There is the use of finger print analysis and DNA gathering. But even with the advancements in video technology, there are, at times, even able to gather evidence using things like facial recognition. And all this evidence that is gathered we can call “identifying markers.” They create a profile of a suspect, a person of interest. Likewise, the identifying markers Matthew uses will point to Jesus as the Messiah.

Matthew, if you are unfamiliar with the book, writes His biographical account of Jesus with the Jewish person in mind. For them, it was of greatest importance to marry the prophetic words of their Scriptures to the identity of their Messiah. And Matthew does this. So the first section of our passage this morning, we can call The Fulfillment of Prophecy.

The entrance of Jesus into Jerusalem is beautiful because of its fulfillment to prophecy and because it brings further clarity to the identity of Jesus as Messiah. If you have your Bibles with you this morning, please turn with me to Matthew’s gospel, chapter 21 and we will begin in verse one.

PRAY

TRIUMPHAL ENTRY

Matthew 21:1–11 - The Triumphal Entry

1 Now when they drew near to Jerusalem and came to Bethphage, to the Mount of Olives, then Jesus sent two disciples, 2 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. 3 If anyone says anything to you, you shall say, ‘The Lord needs them,’ and he will send them at once.” 4 This took place to fulfill what was spoken by the prophet, saying, 

5  “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.’ ” 

6 The disciples went and did as Jesus had directed them. 7 They brought the donkey and the colt and put on them their cloaks, and he sat on them. 8 Most of the crowd spread their cloaks on the road, and others cut branches from the trees and spread them on the road. 9 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!” 10 And when he entered Jerusalem, the whole city was stirred up, saying, “Who is this?” 11 And the crowds said, “This is the prophet Jesus, from Nazareth of Galilee.”

Isn’t that a beautiful scene? In our study through Luke we have seen moments were the crowds respond in joy and excitement to Jesus. We have seen times where they oppose Him. We have witnessed moments were the religious leaders seek to have Him brought down. But here, there seems to be almost unison among the large group of people in the city to Jesus’ entrance.

Jesus and His group of followers are making their way towards Jerusalem and it tells us that they come to the village of Bethphage. This town is located near another town called Bethany which you may recognize as the location of Mary, Martha, and Lazarus’ dwelling. These two villages were located to the east of Jerusalem and as you approached the city you would come to the Mount of Olives which would overlook the city.

It is here that Jesus brings to His side two disciples and gives them a very specific command. He tells them, “Go into the city ahead of us. There you will find a donkey and a colt. Untie them and bring them back. If the owner says anything, simply tell him, ‘The Lord has need of it’ and he will give them to you.”

The reason for such a peculiar and specific command is to fulfill Scripture, which Matthew is kind enough to quote in his passage. Paul, in his letter to the Corinthians would write:

1 Corinthians 15:3–4 ESV

For I delivered to you as of first importance what I also received: that Christ died for our sins in accordance with the Scriptures, that he was buried, that he was raised on the third day in accordance with the Scriptures,

Everything Jesus did in His life, in His death, and in His resurrection was in accordance to the Scriptures and this entry into the city is no different. The prophecy comes from Zechariah. And while we may have labeled Zechariah a minor prophet, his words have major significance because he is quoted over 80 times in the New Testament writings, with the one here perhaps his most famous.

Zechariah 9:9 ESV

Rejoice greatly, O daughter of Zion! Shout aloud, O daughter of Jerusalem! 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.

Now skeptics may argue, “Well, anyone could fulfill this prophecy! They just have to sit on a colt and ride into Jerusalem! This proves nothing!”

And while that may be true, it is the culmination of all the fulfilled prophecies which gives such strong and overwhelming evidence to Jesus as the promised Messiah.

In fact, a conservative estimation of Jesus’ fulfilled prophecies from the Old Testament is roughly 300! Alfred Edersheim found 456 Old Testament verses referring to the Messiah, and J. Barton Payne found as many as 574 verses that point to or describe the coming Messiah.

In other words, while this one particular prophecy could be purposefully fulfilled, the culmination of all of them are too much to argue away.

Now to focus on the prophecy of Zechariah here for a moment, one word really stands out to me in the midst of everything written down. The description of the coming Messiah as humble. The word in the Old Testament prophecies has a deeper meaning than simply lowly in spirit or gentle (which Jesus is, by His own description!).

C.F. Keil states,

The word “humble” denotes the whole of the lowly, miserable, suffering condition, as it is elaborately depicted in Isaiah 53.

If you are unfamiliar with Isaiah 53, I would encourage you to take the time to read it and you will very quickly recognize Jesus in these prophetic words. This passage is known as The Suffering Servant.

The whole picture of this Messiah—this King—is so counterintuitive to the world’s representation of kings. We tend to think of the kings of Scripture as cruel, prideful, waging in bloody battles for their own glory.

But Jesus turns the whole understanding of “King” on its head. He enters into the scene in a lowly stable, being born to lowly parents from a lowly town. His entrance would be entirely insignificant if it wasn’t for what He came to do and who He is as the Son of God!

I have to imagine that as Zechariah was receiving the words to write from the Lord, he may have hesitated when he is told the king of Kings would come into town riding on a donkey!

Caesar’s would ride into cities on golden chariots pulled by a couple of majestic war horses. Kings of old would ride mounted upon their horses. It was highly uncommon for a king to ride upon a donkey. However, one other instance we see of a king riding upon a donkey is in 1 Kings on the day Solomon is recognized as the new king of Israel.

1 Kings 1:33 ESV

And the king said to them, “Take with you the servants of your lord and have Solomon my son ride on my own mule, and bring him down to Gihon.

The reason a king may ride upon a donkey as opposed to a horse is believed to be a sign of peace and humility. Horses were ridden during war time and the donkey would therefore signify a season of peace.

Regardless of significance, it would still be a highly unusual thing to witness.

I’ve always appreciated Douglas Sean O’Donnell’s comparison. He says,

It’s laughable to think about a Roman emperor straddled over such a slow, dirty, undignified, and unpretentious beast. It would be like the President coming into Chicago and traveling down the Magnificent Mile on a tricycle.

330 plus years before Jesus’ entrance, Alexander the Great would stride into Jerusalem upon his war horse at the head of a parade of thousands of troops. That is the kind of entrance we expect of a great king. But again, Jesus is altogether a different kind of king. He is the King of kings!

From the words of Zechariah to Jesus, 500 years have passed. 500 years between the penning of the prophecy to Jesus’ humble entrance upon the colt of a donkey.

So Jesus sends out the disciples, and just as He has told them, there is a donkey and a colt. They return to Jesus with both. In Mark’s parallel account, there in fact is a person who approaches the disciples and asks them what they are doing. They tell him exactly what the Lord told them to say and the man allows them to use them.

It may simply be a passing fact in the story, but I do find it significant because it reveals the fulfillment of Christ’s words and the simple fact that His Word is always true. What He says, what He promises will always come to pass. He promised the disciples on several occasions that “the Son of Man must die” and be raised back to life. It happened. Every time He spoke the words, “Be healed.” The individual was healed.

The Word of God has been, continues to be, and always will be TRUTH.

John 17:17 ESV

Sanctify them in the truth; your word is truth.

Paul, in writing to his protégé, Timothy, calls for him (and all who present God’s Word) to rightly handle the “Word of truth.”

2 Timothy 2:15 ESV

Do your best to present yourself to God as one approved, a worker who has no need to be ashamed, rightly handling the word of truth.

Jesus even refers to HIMSELF as the way, the TRUTH, and the life. So is there significance to Jesus saying there would be a donkey and colt and there is? Maybe not. But it does, however, remind me of the absolute truth of God’s Word throughout the ages. It reminds me that I can rest fully in the fact that His Word will never return void. It reminds me that even when life gets hard that I can trust in the eternal promises of His Word and know that I have been redeemed by the blood of the cross.

Sadly, what I (and we as believers) KNOW to be true is not so easily perceived by a skeptical world. In fact, our culture has adopted the question of Pontius Pilate from John’s Gospel: “What is truth?” (John 18:38)

Ironically, Pilate asked this question to the very One who proclaimed to be the Truth. But this is the world today; everyone is able to carry with them their “own truth.” What they perceive to be true is true, even if it runs counter to another’s truth. And in so doing, truth has become something vague, ever changing, and hard to maintain a hold onto. So by the world’s standard today, truth can change from one day to the next.

But for us, our hope rests upon the solid rock and firm foundation of Christ—the Word incarnate. God is immutable—unchanging. And therefore we know that what His Word said 3000+ years ago remains true today and will remain true to the end of the age. There is no uncertainty with God, and for me, that gives me great confidence and trust in Him and in the Bible. I never have to doubt what I read!

But the debate and worldly doubt we see today is nothing new. In fact, it was just as much a part of culture during the birth and expansion of the early church. We are given an example of this in Acts 26 where Paul makes a Scriptural defense of God’s Word before King Agrippa. And I just want to walk us through this because Paul’s reasoning is so good!

Paul begins by sharing of his own conversion on the road to Damascus, then simply states that everything he preaches and teaches is simply everything the Law and Prophets (the Old Testament) said would come to pass. In other words, Paul is saying, “I am simply presenting the evidence laid before us by God’s Word and it points directly to Jesus Christ of Nazareth.”

Now another man stood present during this discussion; a man by the name of Festus. He was the procurator of the Roman province of Judea. And he retorts,

Acts 26:24–25 ESV

And as he was saying these things in his defense, Festus said with a loud voice, “Paul, you are out of your mind; your great learning is driving you out of your mind.” But Paul said, “I am not out of my mind, most excellent Festus, but I am speaking true and rational words.

Then Paul appeals to Agrippa (who was also a Jew). He says, “King Agrippa, do you believe the prophets? I know that you believe.”

The question implies that if you believe in the prophets then you must believe Jesus to be the Christ because He fulfills them!

That is the question that King Agrippa had to answer in his own heart. And ultimately that is the question we must all answer in our own lifetimes.

Similarly, it is the same question Jesus asked John on the boat. “Who do you say that I am?” All of our eternity rests in how we answer that one question.

Oswald Chambers, author of My Utmost for His Highest, states:

Jesus Christ never asks anyone to define his position or to understand a creed, but “Who am I to you?” Jesus Christ makes the whole of human destiny depend on a man’s relationship to himself.

Oswald Chambers (Lecturer and Missionary)

But He doesn’t do so without first giving us overwhelming evidence (I believe) to be able to answer this question. One of those evidences was His entrance into Jerusalem.

Now let us get to the actual entrance. Let us reread verses 8-11.

Matthew 21:8–11 ESV

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.”

Something I’ve found quite remarkable is that nearly everyone I’ve conversed with about Jesus—believer and unbeliever alike—admire Jesus. They may not see Him as the Son of God. But they find His character, His teachings, and His actions to be admirable. However, Jesus’ actions here leave no room for us to debate upon His identity. It is a bold claim that Jesus makes as He fulfills Zechariah’s prophecy. He isn’t beating around the bush, but openly proclaiming Himself to be the prophesied Messiah!

Douglas Sean O’Donnell calls this the “Audacity of Jesus’ Intentionality.” It really is an ironic moment in the sense that Jesus—who is the perfect reality of humility, and selflessness comes riding upon a donkey and essentially saying, “Here I am. The Messiah of God. Your King has come.” The irony is that this moment is Jesus’ proclamation of his humble reign.

But Jesus has been making proclamations like this throughout His ministry. This is nothing new. Although this may be on the grandest scale yet as He enters a bustling city preparing for Passover, with scores of people before and behind him shouting His praises.

But think of the seven “I Am” statements of John’s gospel. “I am the bread of life.” “I am the light of the world.” “I am the door of the sheep.” “I am the good shepherd.” “I am the resurrection and the life.” “I am the way, the truth and the life.” “I am the true vine.”

I mean, Jesus even said, “Before Abraham was born, I AM” (John 8:58)—the same name God gave Himself in Exodus.

Exodus 3:14 ESV

God said to Moses, “I am who I am.” And he said, “Say this to the people of Israel: ‘I am has sent me to you.’ ”

Usually, we would keep away from someone who seemingly promotes themselves so much. Yet, by Jesus’ actions, His life, His love, His selflessness, His sacrifice—we recognize Him as the epitome of humility.

The great theologian, John Stott simply calls this the “paradox of Jesus.” Stott writes,

[Jesus’] claims sound like the ravings of a lunatic, but he shows no sign of being a fanatic, a neurotic or, still less, a psychotic. On the contrary, he comes before us in the pages of the Gospels as the most balanced and integrated of human beings.

That is the paradox of Jesus! His claims to be deity and yet is beautifully and remarkable humble and gentle and lowly.

Earlier I mentioned “identity markers” in this passage. These clues or pieces of evidence that reveal to us who Jesus truly is in our passage. The first, of course, is His entering on a donkey. The next are given by the shoutings of the crowd as Jesus makes His way through Jerusalem.

THE PROCLAMATIONS OF THE CROWD 1. Hosanna to the Son of David! (v. 9)

The first is the shout of “Hosanna to the Son of David.” The Davidic covenant. Read with me from 2 Samuel.

2 Samuel 7:12–13 ESV

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 proclamations of the crowd further confirm Jesus’ identity as the promised Messiah. He is, after all, from the lineage of king David—hence why his parents travelled to Bethlehem for the census (they were from the house of David).

2. “Hosanna!”

The second identifying marker here is simply the cry of “Hosanna!” We may think of the word Hosanna to simply be a praise such as Hallelujah. But it is quite different. In reality, it is a plea for salvation.

The root word of hosanna is found in the book Psalms.

Psalm 118:25 ESV

Save us, we pray, O Lord! O Lord, we pray, give us success!

The word Hosanna derives from the combining of two Hebrew words. The first is Yasha, which means “deliver, save.” The second is anna, which translates to “I beg of you, or I beseech you.” So when you combine the words—yasha-anna—hosanna—it means “I beg of you to save us!” or “Please deliver us!” Another identifying marker! The Messiah would be their savior. However, the crowd was mistaken by what he was saving them from. N.T. Wright states:

The ‘Hosannas’ were justified, though not for the reasons they had supposed.

N. T. Wright

He would not deliver them from the Roman Empire as they were hoping. His deliverance would be far greater than simply separating the Jews from Roman captivity. His salvation would be on an eternal plane—separating us from sin and death!

So this whole ordeal has stirred up a frenzy in the city. People are coming out of their homes, out of the markets, and flooding the street trying to figure out what’s going on. The wording Matthew uses is, “the whole city was stirred up.” The literal translation of the Greek wording here is that the “whole city quaked.” Just as the city would quake at his death and His resurrection.

And in all the raucous, the people ask the (eternal) life altering question, “Who is this?” Again, the question we all must come face to face with. And the crowd is close, but their answer does not fully envelop the greatness of Christ. They say, “This is the prophet Jesus, from Nazareth of Galilee.”

3. Nazareth.

This brings me to what I believe is yet another identifying marker, however. While Jesus was a prophet in the sense that He did prophecy, He of course was far more than that. He is the Son of God. He is the Messiah. He is the Savior of the whole world. He is the Word of God incarnate. He is the fullness of love, grace, mercy, forgiveness, kindness, justice.

The statement that He was a prophet isn’t the identifying marker. It is that He is from Nazareth.

Matthew 2:23 ESV

And he went and lived in a city called Nazareth, so that what was spoken by the prophets might be fulfilled, that he would be called a Nazarene.

I think it is important to explain this because there is no Old Testament prophecy that says Jesus would be called a Nazarene. Theologians tend to take three positions on this statement from Matthew.

The first position is in the language of the word itself. In Isaiah 11:1, it says that “a shoot will come up from the stump of Jesse.” Obviously referencing the Davidic covenant. The Hebrew word for branch (or shoot) is nester. However, Hebrew words have no consonants so it would be written as NZR. The same first consonants as Nazareth. Thus, NZR and Nazarene would sound very similar.

The second option, which I feel is the weakest of the bunch, is that Matthew references a prophecy outside of the Scriptures.

The third option, which I believe is the strongest argument, is that Nazarene references a person who is “despised and rejected.”

Nazareth was a very small town with a very bad reputation. If you recall, when Jesus calls Nathanael into discipleship, he asks the other disciples, “Can anything good come out of Nazareth?” And there are two main prophecies that point to the Messiah as being despised.

Psalm 22:6–7 ESV

But I am a worm and not a man, scorned by mankind and despised by the people. All who see me mock me; they make mouths at me; they wag their heads;

Isaiah 53:3 ESV

He was despised and rejected by men, a man of sorrows and acquainted with grief; and as one from whom men hide their faces he was despised, and we esteemed him not.

Jesus would also identify Himself as lowly. And the reality of His identity as a Nazarene lines up with the whole of Scripture in that sense.

CONCLUSION So all of this—the riding on a donkey into town, the recognition of His lineage into the line of David, the cry for salvation among the crowd, and his roots in Nazareth all point to and give overwhelming evidence to the identity of Jesus as the Messiah. However, as the saying goes, “You can lead a horse to water, but you can’t make him drink.” Or in the hilarious mind of Gary Larson: (Show image) You can lead a horse to water, but you can’t make him walk on it.”

The facts are presented here to you and me. In a sense, God’s Word has lead us to the living water. But it is up to each of us individually if we choose to drink of it. It is up to you individually if you will proclaim Jesus as Lord and Savior for your own life.

Jesus is our humble King. He is our Savior. May our hearts all cry out, Hosanna! Lord, save us! Jesus was and is our Savior and King and He is coming again. May all our hearts be ready for that great day!

Matthew 24:44 ESV

Therefore you also must be ready, for the Son of Man is coming at an hour you do not expect.

PRAY