Part 5 of “On the Way to Jerusalem”
March 29, 2026 || Glynwood Baptist Church, Prattville, AL || James Jackson, Pastor
Good morning! Please open your Bibles to Luke 19.
My nephew got married several years ago in New Orleans. Since he and his bride both grew up there, they had a traditional “second line” parade.
Do we have any Louisianians who already know what that is?
Alright—then let me explain it for the rest of us.
A second line is a wedding parade through the French Quarter. After the couple is pronounced husband and wife, they lead a procession from the church to the reception.
The bride and groom are out front, holding decorated umbrellas. Behind them is the Grand Marshal—basically a hype man—getting everyone into the spirit of the parade. There’s a live brass band playing jazz, and all the wedding guests are waving handkerchiefs.
And the best part is this—the Grand Marshal invites everyone along the street to join in.
As we made our way through the Quarter, I looked behind me… and I was amazed at how many people had fallen in behind us.
(New Orleans natives don’t need much of an excuse to join a party.)
Tourists lined the streets clapping and cheering as we passed by.
Now I’m sure there were a few folks who were annoyed at the noise and the traffic—but honestly, they were drowned out by the music, the dancing, and the excitement.
But here’s what struck me…
With the exception of our family and invited guests, most of those people celebrating didn’t know the bride or the groom.
And by the next day, they probably wouldn’t have recognized them if they passed them on the street.
When I think about Jesus’ Triumphal Entry into Jerusalem, I picture something a lot like that.
That day—which we celebrate as Palm Sunday—there was a parade.
People cheered.
They waved palm branches.
They spread their cloaks on the road.
They shouted, “Hosanna!”
But when the parade passed…
they went back to whatever they had been doing.
And I can’t help but wonder—
how many of them had no idea who Jesus really was?
And in less than a week…
how many of them were lining the streets for a very different kind of parade?
We’ve been following Jesus on His way to Jerusalem for the past several weeks, and it’s worth taking a moment to look back at where we’ve been.
We began with Costly Commitment—that following Jesus comes at a high cost.
Then we talked about Ultimate Urgency—that the cost of rejecting Jesus is even higher.
We looked at three of Jesus’ parables that show how God invites everyone to the party.
And last week, we saw the ten lepers who were healed—and learned that not everyone responds to that invitation.
So today, on Palm Sunday, we come to Rejoicing and Rejection on the Way to Jerusalem.
Let’s see how Luke tells it. Please stand to honor the reading of God’s Word.
Luke 19:28–44 ESV
28 And when he had said these things, he went on ahead, going up to Jerusalem. 29 When he drew near to Bethphage and Bethany, at the mount that is called Olivet, he sent two of the disciples, 30 saying, “Go into the village in front of you, where on entering you will find a colt tied, on which no one has ever yet sat. Untie it and bring it here. 31 If anyone asks you, ‘Why are you untying it?’ you shall say this: ‘The Lord has need of it.’ ” 32 So those who were sent went away and found it just as he had told them. 33 And as they were untying the colt, its owners said to them, “Why are you untying the colt?” 34 And they said, “The Lord has need of it.” 35 And they brought it to Jesus, and throwing their cloaks on the colt, they set Jesus on it. 36 And as he rode along, they spread their cloaks on the road. 37 As he was drawing near—already on the way down the Mount of Olives—the whole multitude of his disciples began to rejoice and praise God with a loud voice for all the mighty works that they had seen, 38 saying, “Blessed is the King who comes in the name of the Lord! Peace in heaven and glory in the highest!” 39 And some of the Pharisees in the crowd said to him, “Teacher, rebuke your disciples.” 40 He answered, “I tell you, if these were silent, the very stones would cry out.” 41 And when he drew near and saw the city, he wept over it, 42 saying, “Would that you, even you, had known on this day the things that make for peace! But now they are hidden from your eyes. 43 For the days will come upon you, when your enemies will set up a barricade around you and surround you and hem you in on every side 44 and tear you down to the ground, you and your children within you. And they will not leave one stone upon another in you, because you did not know the time of your visitation.”
This is God’s Word. Let’s pray
1. The King Who Comes
Right from the jump, Luke shows us that none of this was random. Jesus is choreographing every element of this scene. He sends two disciples ahead with very specific instructions:
“Go into the village… you’ll find a colt… untie it… bring it to me.”
And He even tells them what to say if someone questions them: “The Lord has need of it.”
And it happens exactly the way He said it would.
That’s not coincidence. That’s control. Jesus is consciously, deliberately fulfilling the prophecy of Zechariah 9, which foretold the Messiah would enter Jerusalem on a donkey.
Now, I want to say just a quick word to any skeptics who might be here or watching online—who may be thinking,
“Well, isn’t this just Jesus arranging things so people would think He’s the Messiah?”
If that’s you, I’m really glad you’re here. I want to honor that question.
But let me gently point out—this is just one of hundreds of prophecies fulfilled by Jesus.
Many of them—like being born in Bethlehem…
or being betrayed for thirty pieces of silver…
or rising again on the third day—
are not things anyone could stage or manipulate.
And there’s something else going on about the donkey that is easy to miss: This is’t the first time a king of Israel has entered Jerusalem on a donkey. Back in 1 Kings 1, when David is preparing for his son Solomon to take the throne, he gives very specific instructions.
He says, “Put Solomon on my own mule… and bring him into the city” And they anoint him as king… and all the people begin to celebrate.
What’s more, Solomon, who’s name is related to the Hebrew word shalom, which means peace, is arguably the only king of Israel whose reign was marked by peace and stability instead of war and conflict.
So when Jesus comes riding in like Solomon… He’s not just claiming to be a king.
He’s declaring what kind of King He is.
A king who comes to make peace between holy God and sinful man.
A king who comes to give life in love, instead of taking life in war.
More than a king— the Prince of Peace.
So how did the crowd react? Did they get it? Not really. They wanted a King who would conquer Rome. They weren’t thinking about a King who would conquer sin and death. So let’s talk about…
2. The Clueless Crowd (v. 36-40)
And underneath that celebration, there’s something else in the air: expectation.
Because Passover isn’t just about what God did in the past—it stirs a hope that maybe He might do it again.
That maybe God might deliver His people… one more time.
And so as Jesus rides along, something starts to happen.
At first, it’s just the disciples doing what Jesus told them to do—bringing the colt, placing their cloaks on it.
But as He begins to move through the city, the response starts to spread.
People start laying their cloaks on the road.
And before long, Luke tells us that “the whole multitude of His disciples began to rejoice and praise God with a loud voice…”
What does Luke mean by “the whole multitude of His disciples.” Typically when we hear “disciples,” we tend to think of the Twelve. But Luke uses that word more broadly. He’s describing the large crowd of people who have been following Jesus—listening to His teaching, watching His miracles, caught up in the movement around Him.
Some are true followers.
Some are curious onlookers.
And some… are just swept up in the moment.
In other words— a lot like a New Orleans wedding parade!
Some know exactly who they’re celebrating. Others just know something exciting is happening, and they want to be part of it.
Now, you might look at the fill in the blank on your listening guide and think, “Wait— why are you calling them the clueless crowd? That’s kinda harsh. How do you know they’re clueless?”
And that’s a great question, because when you look at the text, they’re not saying the wrong things. They’re quoting Psalm 118:26: “Blessed is the King who comes in the name of the Lord!”
These are the right words. This is real praise.
But here’s what Luke wants us to see—and here’s where we need to be careful. Look again at Luke 19:37 :
Luke 19:37 ESV
37 …the whole multitude of his disciples began to rejoice and praise God with a loud voice for all the mighty works that they had seen,
Their praise is real…but their understanding is incomplete.
They are shouting praise for the mighty works of God, but there’s no indication they recognize Jesus as the Word of God.
They’ve been anticipating a Messiah who would save them from Rome, but they don’t yet understand that this Messiah can save them from their sins.
They are ready to give him a crown of gold, but they aren’t expecting Him to take a crown of thorns.
And let’s be honest. Even today, it is possible to see Jesus, to experience Jesus, to be part of the crowd, to say the right things, sing the right songs, show up on the right day, and still not fully recognize who Jesus is.
Maybe we misunderstand His mission— thinking He came so we can have material blessings and financial security.
Maybe we misunderstand His methods— thinking He’s going to use political processes and military might to accomplish His purposes.
Maybe we misunderstand his motivations for coming— that He came to condemn us instead of to seek and to save us.
See, there’s lots of ways to miss the Messiah— to be clueless about the Christ.
The praise can be genuine, but our understanding is limited.
Jesus knew this. And in the next few verses, Luke tells part of the Triumphal Entry story no other gospel writer does—the moment the Coming King becomes the Crying King.
3. The Christ Who Cried (v. 41-44)
In verse 41, Luke turns the camera away from the crowd and back to the King. The noise of the crowd fades into the background, and we see Jesus. This is not what you expect in the middle of a parade. The crowd is shouting. The disciples are praising. The city is alive with celebration. And the King… is weeping.
And this isn’t a quiet tear. The word Luke uses means deep, audible sobbing—even wailing. Jesus is not irritated. He is not frustrated. He is heartbroken.
And listen to what He says:
“Would that you, even you, had known on this day the things that make for peace…”
Do you hear it? You’re celebrating, but you don’t know what actually brings peace. You’re shouting “Hosanna,” but you’re missing the very thing you need.
They thought peace would come through power—through political victory, through overthrowing Rome. But Jesus knows peace doesn’t come that way. Peace comes through repentance, through forgiveness, through the cross He is walking toward.
And then He says something even heavier. He speaks of what’s coming: siege, destruction—not one stone left upon another.
We know from history that all of this was fulfilled less than forty years later. In 70 AD, Jerusalem was destroyed. But don’t miss this—Jesus doesn’t say it with anger. He says it with tears.
A few years ago, I stood on the Mount of Olives at a small chapel called Dominus Flevit—“The Lord Wept.”
And you might have noticed from the picture, the church is shaped like a tear drop.
The church is one of the only Catholic church in the world whose altar faces west. It’s built to face the city of Jerusalem. And as you stand there, you’re looking out over the same city Jesus was looking at in this moment. I remember standing there, seeing that skyline, knowing the history, knowing the conflict, and hearing these words in my mind: “If you had only known the way of peace…”
Judgment is coming, but it is not His desire. The King who will judge is the King who weeps.
And that’s what makes this so personal. Jesus is not distant from people who miss Him. He grieves over them.
The crowd is celebrating, but missing the peace He came to bring. The King is weeping because He sees where that road leads.
Jesus ends this prophecy with a statement that can sound a little cryptic. After warning that not one stone will be left upon another, He says it will happen because “you did not know the time of your visitation.”
Let’s unpack that. Jesus is saying, “I came to you. I stood in your streets. I walked among you. And if you had recognized that, things would have been so different.”
We will never find peace if we do not recognize that God is present with us. So many of our problems—our fears, our insecurities, our temptations, our sins—how many of them would lose their power if we truly believed that God was with us?
We’ve already talked about one of Jesus’ titles: Prince of Peace. Now think about another: Immanuel—God with us.
Jesus Christ came to dwell among us. He fulfilled God’s law and, through His sacrifice on the cross, made peace—peace between God and man, peace within the human heart, and peace among people. And through the message of Jesus Christ—crucified, buried, and risen—we can know the things that make for peace.
And today, you can know them too.
So now we come to a collision of choices. Because Palm Sunday is the day the coming King and the clueless crowd collide. It’s the moment when you have to ask yourself, “What am I looking to for peace?” It is a collision of choices.
You can choose to admire Jesus, agree with Jesus, and talk about Jesus without ever surrendering to Jesus. You can choose a Jesus you create in your own image—a Jesus who blesses your plans, fixes your problems, and works around your busy schedule.
Or you can choose the real Jesus—the One who calls you to repentance, changes your heart, and rules over your life.
You can choose which Jesus you will follow. But only One will bring you peace. Only One has reconciled us to the Father through His death on the cross. Only One has secured our salvation through His resurrection from the dead.
We come to a collision of choices. You don’t get to stand on the sidewalk and watch this parade go by. You’re in it. And the question is not, “What did they do with Jesus?” The question is, “What will you do with Him?”
Jesus said, “Would that you had known the things that make for peace…” And here is the good news: you can know them. Peace is found in a Person, and His name is Jesus.
He is the King who came, the King who wept, and the Christ who was crucified. And today, you have the opportunity they missed—to recognize Him, to receive Him, to surrender to Him. Because the same King who rode into Jerusalem is the crucified, risen, and reigning Lord.
He does not want your applause. He wants your surrender.
Don’t miss your moment of visitation. Don’t miss the peace He came to bring. Because the King has come—and the only question left is: what will you do with Him?
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