Matthew 21:1-11

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Introduction

The Triumphal Entry

21 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.”

We’ve finally made it to chapter 21 of Matthew’s Gospel, and while we still have 8 chapters to go (probably another year and a half at our current pace), this is one of the most significant turning points in Matthew’s Gospel. As far back as chapter 16 Jesus began dropping hints that this time was coming, a time when he would go to Jerusalem, be delivered up to the chief priests, suffer many things, be killed, and finally raised three days later. The disciples still don’t know what to make of it, but now they’re on Jerusalem’s doorstep.
And when Jesus enters Jerusalem he will stir up a hornet’s nest of resistance, a resistance that will ultimately have him killed. Now, while he was in Galilee he frequently avoided the crowds when they attempted to make him king, or when they attempted seize him or throw him off a cliff like in Nazareth, he would often tell men to be silent about his miracles, because this final component of his ministry was still to come, so he avoided it until it was the proper time. And now that time has come, the time in his ministry to announce his identity as Israel’s Messiah and King, to be delivered up to the religious leaders in Jerusalem, to suffer, to die and to be raised. This is what Jesus has been preparing his disciples for over the past 5 chapters.
Now, what I find interesting is that while we still have 8 chapters to go before we reach the end of Matthew’s Gospel (in chapter 28), we only have one week left of Jesus’ life and ministry before he’s crucified. Between chapters 21 and the middle of chapter 28 only one week of Jesus’ time on earth remains. Jesus’ crucifixion will take place during the Passover festival which is only a week away from the events of chapter 21. This is why the crowds are gathering in Jerusalem, some of which are already there when Jesus arrives, with others following him along the road to Jerusalem from Jericho. So in chapters 21-28 Matthew zooms in and focuses on these final events of Jesus’ life and ministry.
And amidst what will take place, or what will happen to Jesus, we will see another major theme, a theme of judgement. Over the next 5 chapters we’ll see that Jesus’ coming to Jerusalem will include God’s judgement against Israel. Jesus will weep as he approaches the city, he will deliver multiple parables against her, he will give the most scathing indictment yet against her religious leaders, and finally, he will tell his disciples of her coming destruction.

Theme of judgement

And, before we begin looking specifically at these 11 verses here in chapter 21 I want to say a little about this theme of judgement, because as we progress through these next 8 chapters I want us to not only have a bird’s eye view of these events, but also a bird’s eye view of why these events play out like they do. Jesus’ crucifixion, for instance, at first, seemed as though God’s plan of sending his Son into the world had failed, for his disciples certainly thought so at first, but we know that this isn’t the case, because in Acts 4:28, the early church confessed shortly after Jesus’ resurrection and ascension into heaven that,

27 for truly in this city there were gathered together against your holy servant Jesus, whom you anointed, both Herod and Pontius Pilate, along with the Gentiles and the peoples of Israel, 28 to do whatever your hand and your plan had predestined to take place.

Jesus’ crucifixion was at the center of God’s plans when He orchestrated the events of history.
Therefore, so were his plans that Israel would reject their Messiah. On one hand He was certainly grieved at their unbelieving hearts, but he also orchestrated his Son’s crucifixion by that unbelief. In fact, it’ll be God’s judgement upon Israel that will also lead to end of the OT sacrificial system, and to the inauguration of the kingdom of heaven.
The earthly Temple and its bloody sacrifices were never intended to be God’s endgame. This is precisely why the book of Hebrews was written, to demonstrate, to show God’s intention to do away with those things that were meant to point ahead to something greater, namely Christ! And since the Messiah has come, the types and shadows must also pass away.
In order for the kingdom of heaven to be established the old must be removed, because something greater has come. In Matthew 12:6, Jesus told the Pharisees,

6 I tell you, something greater than the temple is here.

And while they should have rejoiced, instead they saw Jesus as a threat to their Temple system, a threat to their power, a threat to their influence. As far as they were concerned the Temple system was serving them quite well, it had become and end unto itself, and unless Jesus was there to help them overthrow their Roman oppressors he was merely a threat to their regime.
They had misunderstood the old covenant, all of its laws, and it’s ceremonial practices, they thought these things were a part of the God’s end game, but these things were meant to teach them about Christ, not replace him.
Jesus said in John 5:39-40,

39 You search the Scriptures because you think that in them you have eternal life; and it is they that bear witness about me,

And so everything that the Scriptures prescribed for them to do, from the ceremonial laws to the Temple sacrifices, these things were meant to bear witness to the Messiah, not replace him. These things were meant to point to him and teach them about him, so when they refuse to embrace him Jesus brings judgement.
In the OT the Messiah was expected to bring two thing, the first, salvation, and the second, judgement, but unfortunately they didn’t understand the kind of salvation that he would bring, or that the judgement would be upon them.
So, as we plod our way through these next 8 chapters I want you to keep these things in the back of your mind. I want these things to inform your understanding as we press forward. It’s often said that it’s impossible to see the forest through the trees, so I think it’s important that we often pause to get our bearing before we zoom in a these smaller stories and texts.

Bethphage and the Mount of Olives

Now, that being said, let’s begin there in verse 1,

21 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.”

The first thing I want to do is help get our bearings, especially considering most of us aren’t naturally familiar with these places. If you recall from our last time together Jesus and his disciples have been making their way to Jerusalem from Jericho. Jesus is from Galilee, and at this point he’s probably traveled more than 100 miles on foot from his home in Capernaum. And at this point a large crowd is following him on his final leg to Jerusalem. They’re likely following him for a couple of reasons, the primary being due to his teaching and the miracles that he’s performed in the district of Galilee. The other contributing factor to the size of this crowed is likely to due to the simple fact that the Passover festival is only a week away and that there thousands of people traveling to Jerusalem to celebrate. It’s estimated that about 30,000 people lived in Jerusalem at that time, but that it swelled to something like 180,000 people during the week of Passover, so you can imagine that the volume of foot traffic at this time of year was significant.
Now, Matthew tells us that as Jesus drew near to Jerusalem, he came to a town called Bethphage on the Mount of Olives, which means they had ascended almost 3,000’ since leaving Jericho, and it’s believed that Bethphage was located either at the crest of this mountain ridge or just on the eastern side of it. This ridgeline, known as the Mount of Olives, was only a mile east of Jerusalem, but the two were separated by a large valley known as the Kidron Valley, and from the Mount of Olives they had an incredible view of Jerusalem because the ridgeline rises slightly higher than the city. This also means that the Mount of Olives blocks any view from Jerusalem of seeing the Jordan River valley to the east.
The Mount of Olives has three prominent peaks and was, in Jesus’ day, covered in Olive Trees. It’s where Jesus’ famous Olivet discourse takes place in Matthew 24 when Jesus foretells the destruction of Jerusalem, and is home to the famous grove of Olive trees known as Gethsemane. Unfortunately, in AD 70, when when Rome besieged Jerusalem, eventually destroying the city, the Roman military commander, Titus, cut down all of the Olive trees.
There were actually two small towns located on the Mount of Olives, Bethphage and Bethany. In Mark’s account he actually mentions both of them, and they were both along the road between Jerusalem and Jericho. And Matthew tells us that when they reached Bethphage that he sent two of his disciples into the village to retrieve a donkey for him. And he tells them that if anyone says anything to them that they’re to say, ‘The Lord needs them,’ and that they will send then at once.

Friends in Bethany

Now, at first glance, this seems quite miraculous, and it may very well be, for it wouldn’t have been hard for Jesus to do this, but there’s some interesting circumstantial evidence that the Bible gives us that might indicate something else. The first thing is that they’re near the town of Bethany, which is the same place were Jesus’ friend Lazarus lived, it’s where he died and presumably where Jesus raised him from the dead. John 11:1 says,

11 Now a certain man was ill, Lazarus of Bethany, the village of Mary and her sister Martha.

then in verse 5,

5 Now Jesus loved Martha and her sister and Lazarus.

and then in verse 17,

17 Now when Jesus came, he found that Lazarus had already been in the tomb four days. 18 Bethany was near Jerusalem, about two miles off,

So it’s very plausible, if not likely, that these verses suggest that Jesus already had contacts in-and-around Bethany, which could explain why the owner of the donkey would have permitted Jesus’ disciples from taking the colt and its mother upon their request.

Bethany Jesus’ home base

Bethany also appears to become Jesus’s temporary home base while he’s in Jerusalem for the Passover week. In Mark’s Gospel he says that after Jesus entered Jerusalem that they returned to Bethany that night (Mark 11:11-12) before returning to Jerusalem again the following day. Matthew seems to confirm this later in 21:17 when he also says one evening that Jesus went out from Jerusalem to Bethany and lodged there.
In fact, this isn’t too surprising, given that Passover was at hand. It’s known that, during festivals like Passover, in order to accommodate the massive influx of visitors, Jerusalem’s city limits were extended to the surrounding hillsides, to places like Bethany and Bethphage. While the 33 acre Temple courtyard would have hosted the huge throng of people during the festival, the visitors would have retreated outside of the city to the surrounding villages to lodge overnight.

Fulfilled prophecy

Then in typical Matthew fashion he writes there in verse 4,

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.’ ”

Matthew’s Gospel is the most Jewish of all the Gospel accounts, in other words, he’s writing and appealing to a Jewish audience. He intends to demonstrate that Jesus is the Messiah, the Son of David, the foretold King of Israel, so he’s constantly connecting Jesus to the prophets of the OT. And so he does here, and he actually combines the words of Isaiah with the prophet Zechariah. The first line, ‘Say to the daughter of Zion’ appears to come from Isaiah 62:11, referring specifically to the city of Jerusalem, while the rest of it he quotes from Zechariah 9:9.
Now, I don’t point this out to alarm you but rather to explain that it was very natural and typical for those who were familiar with the Scriptures to conflate, or combine, complementary texts, like Matthew does here. He’s constantly reminding his Jewish counterparts of their Messianic texts to demonstrate Jesus’ fulfillment of them. It was undisputed in his time that Zechariah 9:9 was referring to the Messiah, which also meant that what Jesus was about to do had massive implications.

Jesus’ intentions

And Jesus is obviously not unaware of this text either, as far as we know he’s only ever traveled on foot, yet he takes it upon himself to ride into Jerusalem on a donkey for the last mile of his journey. My point is that Jesus is intentional about his actions, he’s not hiding his identity, he’s going to waltz right into Jerusalem, the City of David, on a colt, just as it was predicted by the prophet Zechariah. Jesus’ intentions are clear, and he doesn’t have to say a word.
I’ve sometimes been asked why Jesus didn’t make it more clear to who he claimed to be, but I think we only ask that question when we don’t realize that what Jesus did, such as in this text, spoke much louder than anything he could have ever said. Often it’s only because we don’t understand the degree to which Jesus’ actions fulfilled OT prophecies that we ask those kind of questions. On one hand Jesus’ identity was shockingly clear, yet on the other hand we can see why Jesus put on the brakes when it wasn’t yet time for him to be crucified, but now, here in chapter 21, that time has ended, and it’s why they’ll crucify him only one week later.

The red carpet

But before he enters the city Matthew writes there in verse 8,

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!”

Now, when they spread their cloaks (or what we might call their jackets) on the road in front of Jesus, along with these Palm branches (that John identifies for us in his Gospel), they’re essentially laying out an impromptu red carpet for Jesus. This symbolized the honor given to political leaders, such as governors and kings. For instance, in 2 Kings 9:13 when the writer describes the northern kingdom anointing Jehu as their king, it says,

13 Then in haste every man of them took his garment and put it under him on the bare steps, and they blew the trumpet and proclaimed, “Jehu is king.”

And as they began to do this Matthew says that the crowd also started to shout, “Hosanna to the Son of David!” “Hosanna in the highest!” “Blessed is he who comes in the name of the Lord!” This word, ‘Hosanna’, meant, “Save, please,” or “Save, now.” But, by Jesus’ day it had become an expression, or a shout of praise, drawn from Psalm 118 concerning the Messiah, along with the phrase, “Blessed is he who comes in the name of the Lord!” Kind of like how the word, ‘Hallelujah’, originally meant, “God be praised!”, but is used in worship as a shout of rejoicing. And when the crowd would shout, “Hosanna in the highest!” it was a reverent way to speak of God in heaven. (Matthew Commentary, R.T. France, p. 780)
So imagine this Galilean crowd laying their cloaks and palm branches before Jesus as he entered Jerusalem on a donkey’s colt, chanting “Hosanna in the highest!” It’s crystal clear what’s happening here, and Jesus, in a very real sense, has started it. Jesus is not sneaking quietly into Jerusalem.

Jerusalem stirred up

Then Matthew writes there in verse 10,

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.”

Now, what I want you to see is the clash between this foreign Galilean crowd, who is ushering Jesus into Jerusalem on a colt, and the city of Jerusalem.
In the Gospel of John, we also learn that even the Galilean crowd that had already gathered in Jerusalem ahead of Jesus came out to join them. We read in John 12:12 that,

the large crowd that had come to the feast heard that Jesus was coming to Jerusalem. 13 So they took branches of palm trees and went out to meet him, crying out, “Hosanna! Blessed is he who comes in the name of the Lord, even the King of Israel!”

And so when Jesus enters Jerusalem, Matthew says, that the whole city was stirred up, saying, “Who is this?” And the crowds respond, “This is the prophet Jesus, from Nazareth of Galilee.”

Jesus causing a commotion

Now, I want you to think about what this means in light of everything we know about Jesus and Jerusalem. Think back to Matthew 2:3 when Herod was king and Jesus was born in Bethlehem, just south of Jerusalem. Think of what Herod’s reaction was when wise men came from the east asking, “Where is he who has been born king of the Jews?” Matthew said that,

3 When Herod the king heard this, he was troubled, and all Jerusalem with him;

and that Herod secretly sought out Jesus in Bethlehem to kill him, but when the Magi foiled his plan he killed every male child in Bethlehem and the surrounding region who were two years and under. Jesus was seen as threat to Herod’s rule so he sought to kill him, and because he was a threat to Herod Jerusalem feared how this new-born king might get them in trouble with the Roman government. And so again, Jerusalem is rightfully troubled at Jesus’ entrance into Jerusalem.

Jesus their political leader

Now, also remember, the crowds intended Jesus to be their political deliverer, they didn’t realize that it wasn’t political deliverance that they needed, but rather to be set free from their sin.
And as Christians, we too, so often seek political deliverance over against the deliverance from sin (whether it be our own, or our neighbor’s), we’ll spend time arguing politics and the dangers of a particular presidential candidate while remaining silent concerning the need for salvation from sin. We’re willing to engage our neighbor on the peripheral items, to try and treat the symptoms while neglecting the true sickness - mankind’s sin. This is why the Gospel is so important, this is why evangelism is so important, because it addresses the root of our problems, both in ourselves and our neighbor. The Gospel addresses the deadly nature of sin, and it offers deliverance from it. And when we neglect the Gospel in our conversations with others we neglect the most important news in the world.
Itinerant preacher Voddie Baucham once said,
“We are not seeing terrible things in our culture because we vote the wrong way. We are seeing terrible things in our culture because men love darkness rather than light.”
Israel didn’t need a political leader to overthrow Roman oppression, they needed deliverance from their sin, but since they were so blind to that need, their Messianic expectation was clouded by their earthly desires for a mere political system (Mark 11:10). Like the disciples, who misunderstood the nature of the kingdom that Jesus preached, Israel misunderstood the very mission of the Messiah himself. So even those who threw palm branches and their cloaks before him were completely unaware of Jesus’ intentions and the nature of his mission. While they were right to honor him as King, and to cry “Hosanna!”, they expected him to save them from Rome, while he intended to deliver them from their sin. This is why Jesus’ crucifixion was such a shock to his followers, it’s why it was such a shock to even his closest disciples.

Conclusion

But despite the wrong intentions of the Galilean crowd, and the threat that Jesus posed to Jerusalem’s security and it’s religious systems, God would have his way, Jesus’ kingdom would prevail, and he would save his people from their sin. The perfect storm had been orchestrated by God’s hand of providence, despite the mess Jesus would encounter at Jerusalem, despite being delivered up to the chief priests, despite enduring unthinkable suffering, and being crucified on a cross. Jesus would triumph, he would be raise three days later and ultimately ascend to be seated at the right hand of the Father on his throne. No one could stop him.

Prayer

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