Luke 19:28-44 – The Un-Triumphal Entry

Hi ho Silver, away!

It was Palm Sunday as Jesus rode into Jerusalem. He sat on a blazing white stallion that kicked up a cloud of dust as he pranced through town.

The people Jesus passed were in awe of such a beautiful animal, but they were even more awestruck by the man who rode it. As Jesus passed by, you could hear the people say, “Who was that masked man?” and “Did you see His Sword?

But He didn’t have time to stop. There were bad guys on the loose and Jesus had a job to do.

As He rode into Jerusalem He quickly sized up the situation and formed a plan to capture the ring leader of the trouble makers. His name was Diablo, although some called him Satan.

Diablo didn’t like it that Jesus was on the prowl in his streets, so when he heard Jesus was in town, he loaded his pistols, sent his sidekicks out to set up an ambush. Then, kicking wide the squeaky saloon doors, he stepped out into the dusty street.

The crowds ran for cover. They knew to keep clear when Diablo had that look in his eyes.

But Jesus wasn’t afraid. He got down off of His stallion, silver pistols and white chaps gleaming in the sun. He clenched his fists, popped his knuckles, made that squinty eyed grimace, and said, “Go ahead…make my day.”

Amazingly, Diablo did. A couple of shots were fired, there was a short scuffle, and Jesus won handily over Diablo and his minions.

Jesus hog-tied them all and threw them in jail.

The crowds of people reappeared, and began to ask Jesus to be their new sheriff.

But with a great leap, He mounted His horse and pulled hard on the reigns. The stallion stood on its hind legs, neighed loudly, and pawed the air with its front legs. When it stood as tall as it could stand, Jesus leaned forward in the saddle. Holding the reigns with one hand while lifting his white hat in the air with the other, He shouted with a loud voice, “I’ll be back.”

As Jesus rode off into the sunset, the background music swelled to a crescendo, and the credits began to roll…

Isn’t that how you would have done it if you were Jesus? It’s what I would have done. It’s probably what Hollywood would have done. But Jesus always does things differently. He never did things the way any one of us would have done them.

As we look at what really happened 2000 years ago when Jesus did enter Jerusalem, it is not what any of us would have done.

Luke 19:28-44 sets the scene. This passage contains the first event in Christ’s final week—the event known as the Triumphal Entry. But as we will see, it is anything but “Triumphal.”

A “Triumphal Entry” would be like the one I just described a few minutes ago. A Triumphal Entry would be what the Jews were looking for. A Triumphal Entry would have included Jesus defeating Satan and overthrowing the Roman domination of Israel. A Triumphal Entry would have had Jesus set up as King and Ruler and Judge.

But none of those things happened. This event is called the Triumphal Entry, but that is not really what it was.

1. What Jesus Did (Luke 19:28-35)

Luke 19:28. When He had said this, He went on ahead, going up to Jerusalem.

As Bible students, the first question to ask of this text is, “When He had said what?” Just prior to this event, Jesus told the parable of a nobleman who went to a faraway land to be crowned king. As he was leaving, he gave ten minas to ten servants, and told them to invest it for him while he was gone. The parable tells us about three of these servants, what they did with their money, and how the master rewarded them when he returned as king … or punished them, as was the case with the third servant.

That is the parable Jesus had just finished telling, and now in Luke 19:28, we see that when he had said this, he went…up to Jerusalem.

While some see this as a parallel between Jesus going up to Jerusalem and the master in the Parable going into a foreign country, this is not the proper parallel we should make. After all, Jesus does not go into a foreign country, but just up to Jerusalem. The parallel with the preceding parable is with the third servant, the one who hid his talent and so was condemned and cast out by the master. This is what will happen to Jesus when He enters into Jerusalem. He did not play by the rules of this world and gain more money and power for Himself, and so the religious and political powers of this world will do all they can to destroy Him. (See this explanation of the Parable of the Talents for more on this idea).

Let us see how this unfolds.

Luke 19:29. And it came to pass, when He came near to Bethphage (means House of Unripe Figs) and Bethany (means House of Many Figs).

I don’t think it is accidental that these two towns are mentioned here. The fig tree was always representative of God’s blessing on Israel. One of the covenant promises God made with Israel was that when they were obedient to Him, he would bring them peace and prosperity. This was symbolized by “each man having his own vine and his own fig tree” (1 Kings 4:25; cf. also Hos 9:10; Isa 36:16).

Jesus has just told a parable about how he wants his servants to be productive while he is away. And now, in Luke 19:29, Luke mentions both Bethphage—House of Unripe Figs, and Bethany—House of Many Figs, and the question in the reader’s mind then was, “When Jesus enters Jerusalem, which of the two will he find the Jews to be?”

We know that Jesus is going to find a barren Jerusalem. He is going to find a fig tree of unripe fruit. And in fact, we know from the accounts in Matthew and Mark that the very next day, He illustrates this by cursing the barren fig tree. Do you remember? On Monday morning, He is hungry, and he comes upon a fig tree which has no fruit, so He curses it, and when they all return that night, the tree has withered and died (Matt 21:19-20; Mark 11:13-14, 20).

It was not the season for figs, but this was all symbolic of what Jesus expected to find in Jerusalem…but did not.

Continuing on with Luke 19:29 then, but stating that they were at the mountain called Olivet. This is the Mount of Olives. Again, some symbolism is implied here. First of all, prophetically, Jesus is the Olive shoot out of the stump of Jesse. During Jesus’ final week, He spent a lot of time on the Mount of Olives, and in fact, His final night was spent praying in the Garden of Gethsemane on the Mount of Olives, which means “Garden of the Olive Press.” Most likely, it was on an olive press that Christ prayed, and because of the great pressure that was upon Him, shed drops of blood. He, as the Olive shoot, was pressed like an olive.

But the Mount of Olives is important for another reason. Zechariah 14:3-4 prophecies that when the Messiah comes to set up his earthly kingdom, He will come to the Mount of Olives. The Jews knew of this prophecy, and look at what the result would be. In 14:9, 11, the Mount of Olives will split in two, and He will set up His throne in Jerusalem. So every time Jesus drew near to the Mount of Olives, the disciples got excited.

This sets us up for what happens next. If we had never read this account before, and if we were Jews looking for the Messiah’s coming, we would be expecting Christ to overthrow the Romans and set up His earthly rule.

But in Luke 19:29 and following, He gives his disciples some very curious instructions.

Luke 19:29-35. He sent two of His disciples, saying, “Go into the village opposite you, where as you enter you will find a colt tied, on which no one has ever sat. Loose it and bring it here. And if anyone asks you, ‘Why are you loosing it?’ thus you shall say to him, ‘Because the Lord has need of it.'”

So those who were sent went their way and found it just as He had said to them. But as they were loosing the colt, the owners of it said to them, “Why are you loosing the colt?”

And they said, “The Lord has need of him.” When they brought him to Jesus. And they threw their own clothes on the colt, and they set Jesus on him.

The fact that the colt had never been ridden makes it specially suited for sacred purposes. For example, the red heifer which was to be used in ceremonies of cleansing was to be a beast upon which the yoke had never come (Num 19:2; Deut 21:3). The cart on which the ark of the Lord was to be carried had to be one which had never been used for any other purpose (1 Sam 6:7). So this was a young, never-before-ridden donkey.

Another thing we notice about what Jesus does, is that He is borrowing this donkey. This might seem strange, but it was actually a fairly common practice in that day. When a royal emissary arrived in town, they would often borrow (or commandeer) a mount to ride into town on. It was considered a privilege to have your mount used by the king or prince or general or famous teacher who was riding into town (cf. Gen 49:10-11). The interesting thing, however, is that most often, the royal emissary found the most beautiful and proud stallion in the city to ride in on. This would show victory and conquest.

But the donkey colt was just the opposite. It shows humility and peace. Christ did not want to enter Jerusalem riding a horse, or driving a chariot. He did not wear a crown, or carry a sword as most royal persons would have done. Donkeys were used occasionally, but when they were, they were for civil, not military processions (1 Kings 1:33).

This is all important because we’re going to see that the people thought they were getting a military Messiah. Someone who was going to judge and fight and rule. Christ wanted them to see Him differently. So when He rides in on a donkey, this was His way of saying, “I come in peace.” He came not to destroy, but to create. Not to condemn, but to help. Not in the might of arms, but in the strength of love. Jesus was definitely making a claim.

The multitudes recognized a claim—but not the one Christ was trying to make. We’ve seen first, what Jesus did. Luke 19:36 shows us, secondly, what the crowds did.

2. What the Crowds Did (Luke 19:36)

Luke 19:36. And as He went, many spread their clothes on the road.

Spreading of garments represents royal homage (2 Kings 9:12-13). It was a sign of paying tribute—like rolling out the red carpet today. By laying down their cloaks, they were giving Jesus a kingly welcome.

But this is only the first thing they did. They do a couple of other things, like cheering and waving palm branches…but all of these things reveal thirdly, what the crowds wanted.

3. What the Crowds Wanted (Luke 19:37-40)

Luke 19:37. Then, as He was now drawing near the descent of the Mount of Olives, the whole multitude of the disciples began to rejoice and praise God with a loud voice for all the mighty works they had seen.

We know from the other Gospel accounts that most of these people here were pilgrims from Galilee (many of them were disciples; Luke 19:37) or Jericho (Matt 20:29). All of them were most likely here for the Passover and the Feast of Unleavened Bread.

Maybe you are thinking, “The verse mentions a multitude. How many people were there?”

In AD 60 (30 years after this event, a Roman governor took a census of the number of lambs that was slain in Jerusalem during this week, and found that it was close to 250,000 lambs! Jewish law stated that there must be a minimum of ten people for each lamb slain, so during this time, there would be at least 2.5 million people in or around Jerusalem![1] There was no better time for him to be revealing himself, for a large portion of the Jewish people were there. Being from Galilee, they had seen (or heard about) many of His miracles (Luke 19:37), and heard some of His teachings. Jesus normally avoided Jerusalem, so He was relatively unknown there.

Luke 19:37 also tells us that these disciples were rejoicing and praising God with a loud voice. Luke 19:38 tells us what exactly they were saying.

Luke 19:38. saying: ‘Blessed is the King who comes in the name of the LORD!’ Peace in heaven and glory in the highest!”

Multitudes, cheering for Him here. Luke’s account kind of translates for us what they were saying, but the other accounts tell us that they were also shouting, “Hosanna!” Hosanna means “Save us, Oh God!” and comes from the Psalms. Specifically, the people here were reciting Psalm 118:25-27. So we hear this, and think they were recognizing Christ’s divinity and Messiah-ship.

But really, shouting this was not too much out of the ordinary. Jerusalem sat on a hill, that is why whenever people travel to Jerusalem, the Bible reads that they went “up” to Jerusalem. During this time of the year, as I mentioned, millions of pilgrims would make the journey up to Jerusalem for Passover and the Feast of Unleavened Bread.

And as they approached Jerusalem, they would sing certain psalms which are known as the Songs of Ascent. At a certain point on the road, they would begin with Psalm 113, and as they got nearer and nearer to Jerusalem, would sing through Psalm 114, 115, 116 and 117 so that as they entered into Jerusalem, they were singing Psalm 118.

And many of these pilgrims, in the joy of the moment, would stop right outside the gates of Jerusalem, and welcome other pilgrims by joining them in song as they walked the final few steps to Jerusalem. So as these pilgrims were approaching Jerusalem, they would be singing the final few lines of Psalm 118, and as they did, the throngs of people, the multitudes would welcome them by joining them in singing.

What were these final words they would sing?

“Blessed is he who comes in the name of the Lord. Hosanna in the highest. Blessed is he who comes in the name of the Lord. Hosanna in the highest.”

Can you imagine? As you approach the holy city of Jerusalem, to celebrate one of the most holy days of the Jewish Calendar, thousands of people would greet you and join with you in song. I think that’s what entering heaven might be like.

So, as Jesus entered, the multitude of people was just singing as they normally did to welcome other travelers. But the thing that was different about this Traveler, was that He rode in on a donkey in fulfillment of prophecy. And some who recognized this, began to lay their coats at His feet in welcome, and wave palm branches before Him as well.

They were giving Him a royal welcome. As I said, the coats were like rolling out the red carpet, and the branches were a symbol of paying homage to rulers (1 Macc 13:51; 2 Macc 10:7).

They also slightly changed the words of the song for Jesus. Rather than “Blessed is he who comes in the name of the Lord” (Psalm 118), they sang “Blessed is the King who comes in the name of the Lord.” This reveals that they wanted a KING. So while the singing was not out of the ordinary, the donkey, the coats, the palm branches and the specific words of the song were. These things were signs of royalty. The crowds revealed through this that they wanted a ruler, a judge, a KING. They wanted a warrior.

Of course, as always in the Gospels, there were religious leaders nearby. And when they saw what the crowds were doing, they recognized the prophetic implications, and look what they say in Luke 19:39.

Luke 19:39. And some of the Pharisees called to Him from the crowd, “Teacher, rebuke Your disciples.”

They have had run in after run in with Jesus, and…they can’t stand Him. In fact, they are looking for ways to kill Him (Luke 19:47).

Luke 19:40. But He answered and said to them, “I tell you that if these should keep silent, the stones would immediately cry out.”

What does Jesus mean? Why is it so important that He be hailed and honored on this day in history?

Luke 19:41-44 tell us why. We have seen What Jesus Did, What the Crowds Did, and What the Crowds Wanted. Let us now look at what Jesus wanted.

4. What Jesus Wanted (Luke 19:41-44)

Luke 19:41-44. Now as He drew near, He saw the city and wept over it, saying, “If you had known, even you, especially in this your day, the things that make for your peace! But now they are hidden from your eyes. For days will come upon you when your enemies will build an embankment around you, surround you and close you in on every side, and level you, and your children within you, to the ground; and they will not leave in you one stone upon another, because you did not know the time of your visitation.”

Over and over again in the Gospels, Jesus warns His followers not to tell anyone who He is. The reason He nearly always gives is that His time had not yet come. (Mt. 8:4; 9:30; 12:16; 17:19; John 6:15.)

But now we come to the Triumphal Entry. Everything He does over the next few days was designed to call attention to the fact that He is the Messiah. His time had come. In Luke 19:41, Jesus wept over Jerusalem. Why? Because in Luke 19:42, they did not know what day it was.

You say, “Well, what day was it? Why was it so important for Jesus to be recognized on THIS day?”

There is a famous prophecy in the book of Daniel, which was written about 600 years before Christ came to earth, which foretold the exact day Christ would enter Jerusalem! The prophecy is known as Daniel’s 70 weeks, and is found in Daniel 9:24-26. It foretells the exact day Jesus was to enter Jerusalem. Most believe that this day was April 6th, AD 33.

And in Luke 19, the religious leaders of the day want Jesus to keep His disciples quiet. And what does Jesus say? If they kept quiet, the very stones would cry out! There was no keeping quiet on this day in history. And Jesus wanted His own people to recognize him for who He was…but they did not. And so in verse 41 and 42, He weeps over the city because they did not recognize what day it was (cf. Jer 6:26; 8:18-9:3; Lam 1:1-4)!

We tend to make excuses for them. We look at that prophecy in Daniel and say “It’s pretty confusing.” But Jesus wanted them to know, and even expected them to know. In fact, God, in Deuteronomy 4:29, commanded them to know. In other words, there was no excuse for their not knowing.

If they had been in God’s Word as they should have been, THEY WOULD HAVE KNOWN WHAT DAY IT WAS!

And here, as Christ enters into Jerusalem, the scene makes Him cry. They shout “Blessed is He who comes in the name of the Lord. Hosanna in the Highest.” They lay their cloaks before his donkey. They wave palm branches. They are honoring him with their words and their actions, but their hearts are far from Him (Isa 29:13; Matt 15:8).

Some of them, undoubtedly, thought that he was the promised Messiah, but they all wanted the Messiah who would rule and judge and set up an earthly Kingdom. In all likelihood, not one of them understood what kind of Messiah He had come to be. The disciples didn’t even understand until after Jesus had died and risen from the dead. But all of them, the disciples and the multitudes should have seen. They should have known. It was everywhere in Scripture. It was plain before their eyes. He had clearly taught it and explained it. He was even riding in on a donkey—a symbol of peace and humility—not victory and conquest.

But they did not understand.

All history had pointed toward this single, spectacular event when the Messiah publicly presented Himself to the nation, and they did not recognize Him. The religious leaders—who of all people should have known because they prided themselves in their knowledge of the Scriptures—told Jesus to tell the multitudes to keep silent. (Luke 19:39).

As a result of not recognizing who He was and what he had come for, Jesus tells them what will happen in Luke 19:43-44. This is exactly what happened. In AD 70, the temple was destroyed. The Jews were scattered. What Jesus said came true—all because they did not recognize Him as He wanted.

So from Luke 19:28-44, we’ve seen what Jesus did, what the crowds did, what the crowds wanted, and what Jesus wanted.

As Christians who are living 2000 years later, the passage still speaks to us. It asks us,

5. What do You Want, and What Will You Do?

First of all, who do you think Jesus is, and what do you think He wants? Many think He was just a good teacher or a prophet. But He claimed to be God. Would Jesus be disappointed with who you think He is?

And lest we be too critical of Jerusalem on that day, ask yourself this question: What city even today would not be shaken by Jesus’ entry into it? Imagine Jesus entering New York, Los Angeles, Washington, or Dallas? If we even recognized him, I’m sure we’d welcome him with our hosannas—at first, anyway. We’d line the streets and strike up the band and have a grand parade right down Main Street. But I’m equally sure that, by the end of the week, we’d have Him nailed to a cross, too.

Why? Because the Kingdom Jesus came to establish still threatens the kingdoms of this world—your kingdom and mine—the kingdoms where greed, power, and lust rule instead of grace, mercy, and peace. And who among us really wants to surrender our lives to that Kingdom and that King? So let us not be too hasty in judging them.

Secondly, are you looking for His reappearing?

The first time He came, they should have known exactly what day He would appear. God has not given us such information about Christ’s second appearing when we will be raptured to meet Him in the air. He said that no one can know the day or the hour (Mt. 24:36). And as a result, many of us have simply given up watching and waiting for His coming. But that is not what we are supposed to do.

Even though we cannot know the day or the hour, we are to be ready for His coming. It could be any day. It could be today. It could be tomorrow. There is nothing else that needs to happen before the church is taken away (Jas 5:7-9; 1 Pet 4:7; Heb 10:24-25; 1 Thess 5:1-4; Titus 2:11-13; Matt 16:1-3).

We are supposed to know the times we live in. We are to understand the times. We are to be eagerly awaiting the Lord’s coming—even though we cannot know the exact date.

I began this morning by describing the way we normally would imagine Christ’s coming if we had been able to write the script. But that’s not the way he came the first time.

You know what though? It’s no too far off from how his second coming will be. Let me close this morning by reading a few verses from Revelation 19.

Now I saw heaven opened, and behold, a white horse. And He who sat on him was called Faithful and True, and in righteousness He judges and makes war. His eyes were like a flame of fire, and on His head were many crowns. He had a name written that no one knew except Himself. He was clothed with a robe dipped in blood, and His name is called The Word of God. And the armies in heaven, clothed in fine linen, white and clean, followed Him on white horses.

Now out of His mouth goes a sharp sword, that with it He should strike the nations. And He Himself will rule them with a rod of iron. He Himself treads the winepress of the fierceness and wrath of Almighty God. And He has on His robe and on His thigh a name written: KING OF KINGS AND LORD OF LORDS.

Are you waiting for this? Are you ready for this? I would suggest that you get ready, for Christ is coming, whether you are ready or not.

Yet there is something even more important about this text than just looking for the second return of Jesus.

When Jesus came the first time, most of the religious people were looking for a Warrior Messiah. A Messiah who would raise an army and crush, kill, and slaughter the enemies of Israel.

But this is not why Jesus came. And though the people hailed Him as King, they wanted a different sort of King than the King He had come to be.

He wanted them to see that He loved their enemies as much as He loved them. That he forgave their enemies, just as He had forgiven them. That He welcomed both the Israelites and their enemies into one family of the Redeemed.

But they did not see this, and so He wept over the city.

And I often wonder if Jesus weeps over us.

Though we now know why Jesus came the first time over 2000 years ago, many of us expect that in His second coming, He will come as a Warrior King. We want Him to raise an army (or bring one with Him) so that He can crush, kill, and slaughter all our enemies.

Could it be that we have fallen into the same trap as our spiritual forefathers? Could it be that just as they wrongly wanted a Messiah who would kill and slaughter others, so also, we are wrongly hoping for a Messiah that will kill and slaughter ours?

Maybe, just maybe, when Jesus comes again, it will not be to kill our enemies and let their blood flow through the city streets. Maybe, just maybe, when Jesus comes, it will be to forgive all, accept all, love all, and bring peace to all.

Maybe, when Jesus comes again, riding that white horse of victory, the victory He declares is not over our physical foes, but over the spiritual foes of sin, death, and devil.

Maybe, when Jesus comes again, with a robe dipped in blood, it is not stained with the blood of our enemies, but with His own blood, shed for our us and for our enemies.

Maybe, when Jesus comes again, with the shining sword at His side, it is not a sword for dealing death, but a sword of the Spirit and the Word of Truth, which reveals to us all who we really are and what God is truly like.

The crowds wanted a king who would kill their foes. They were wrong. We want a king who will kill our foes…

Are you looking for the second coming of Jesus? If so, make sure that when you do, you take cues from His first coming for how His second coming will look. For if we don’t, we may not recognize Him at His coming, and He may weep over us, just as He wept over them.