Jesus came in a donkey in a victory parade of sorts (though humbly and nothing like the Roman parade). But excitement was in the air. 2.5 million people were in town for the passover. Jesus was normally very quiet about his ministry. Would heal people and then tell them not to tell anyone about him.
"Then Jesus said to him, “See that you don’t tell anyone. But go, show yourself to the priest and offer the gift Moses commanded, as a testimony to them.” Matthew 8:4
Why did this happen? Did Jesus give the crowds what they wanted so all would see it wouldn't be as they thought it would? They wanted a conquering hero. Jesus came in on a donkey proclaiming peace, but there was no conquering Rome. He had to first conquer sin.
Remember the streets were crowded with people. Celebration feeling in the air. Parties. Reunions. People planning this for a year.
"As they approached Jerusalem and came to Bethphage on the Mount of Olives, Jesus sent two disciples, 2 saying to them, “Go to the village ahead of you, and at once you will find a donkey tied there, with her colt by her. Untie them and bring them to me. 3 If anyone says anything to you, say that the Lord needs them, and he will send them right away.”
"This took place to fulfill what was spoken through the prophet:
5 “Say to Daughter Zion,
‘See, your king comes to you,
gentle and riding on a donkey,
and on a colt, the foal of a donkey.’”[a] Matthew 21:1-5 (and quoting Zechariah 9:9)
Matthew was a Jewish writer writing to a Jewish audience. He knew how important it was to show that Jesus fulfilled prophecy.
"From that time on Jesus began to explain to his disciples that he must go to Jerusalem and suffer many things at the hands of the elders, the chief priests and the teachers of the law, and that he must be killed and on the third day be raised to life." Matthew 16:21
Jesus knew why He was going to Jerusalem. He had tried to prepare His disciples to face His death.
"The next day John saw Jesus coming toward him and said, “Look, the Lamb of God, who takes away the sin of the world!" John 1:29
John the Baptist knew who Jesus was right away!
Prior to going to Jerusalem, Jesus spent time with Lazarus, Martha and Mary in Bethany. Between Bethany and Jerusalem they would go over the Mount of Olives (called this because it was covered in Olive trees). Jesus would look down on Jerusalem before He arrived.
"As he approached Jerusalem and saw the city, he wept over it 42 and said, “If you, even you, had only known on this day what would bring you peace—but now it is hidden from your eyes." Luke 19:41-42
Jesus told the disciples where to find a donkey for the procession. They did exactly what He told them to do.
"The disciples went and did as Jesus had instructed them. 7 They brought the donkey and the colt and placed their cloaks on them for Jesus to sit on." Matthew 21:6-7
Cloaks and branches were laid down to cut the dust. This was the "red carpet" treatment!
"A very large crowd spread their cloaks on the road, while others cut branches from the trees and spread them on the road. 9 The crowds that went ahead of him and those that followed shouted,
“Hosanna[a] to the Son of David!”
“Blessed is he who comes in the name of the Lord!”[b]
“Hosanna[c] in the highest heaven!” Matthew 21:8-9
Palm branches and the shout "Hosanna" were signs of victory. Hosanna is a victory chant. The city was shaken (like in an earthquake) with the crowd's enthusiasm. So much fanfare the ground shook.
There people had huge expectations for Jesus, what Jesus would do for them. They thought they were going to gain from Jesus -- gain physical freedom from Rome. Be free from Rome's taxes. People quickly got disillusioned with Jesus because they didn't cash in with Jesus as they thought they would. Jesus never promises a life of ease. There is only one place in the Gospel where Jesus uses the word "easy."
“Come to me, all you who are weary and burdened, and I will give you rest. 29 Take my yoke upon you and learn from me, for I am gentle and humble in heart, and you will find rest for your souls. 30 For my yoke is easy and my burden is light.” Matthew 11:28-30
God's great promise is His presence, not a life of ease. His promises aren't for material junk.
"When Jesus entered Jerusalem, the whole city was stirred and asked, “Who is this?”
11 The crowds answered, “This is Jesus, the prophetfrom Nazareth in Galilee.”Matthew 21:10-11
(Where "stirred" is used in this verse is where the ground shook with excitement)
The people are shouting for Him. Jesus is in tears (see Luke 19:41-42) over their blindness.
"As he approached Jerusalem and saw the city, he wept over it 42 and said, “If you, even you, had only known on this day what would bring you peace—but now it is hidden from your eyes." Luke 19:41-42
They didn't get it. They didn't understand why Jesus was there. Nobody was getting it. They were twisting all of it to their own agendas. He promises redemption, His presence, Eternal life. Before victory there has to be the sacrifice for sin.
Jesus is coming back as a warrior eventually. See below:
"I saw heaven standing open and there before me was a white horse, whose rider is called Faithful and True. With justice he judges and wages war. 12 His eyes are like blazing fire, and on his head are many crowns. He has a name written on him that no one knows but he himself. 13 He is dressed in a robe dipped in blood, and his name is the Word of God.14 The armies of heaven were following him, riding on white horses and dressed in fine linen, white and clean." Revelation 19:11-14
Jesus wasn't offering revolution but repentance on Palm Sunday.
What does your life say Jesus is? When People see Jesus through you, what do they see?