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This is Matthew’s account of Jesus’ arrival into Jerusalem (as found in Matthew 21, with some details in bold print added from Luke 19.)

As they approached Jerusalem and came to Bethphage on the Mount of Olives, Jesus sent two disciples, 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 that no one has ever ridden. Untie them and bring them to me. 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: “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.’” The disciples went and did as Jesus had instructed them. They brought the donkey and the colt and placed their cloaks on them for Jesus to sit on.

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Worth noting: Riding on a donkey was something a very particular kind of King did.

“In the ancient Middle Eastern world, leaders rode horses if they rode to war, but donkeys if they came in peace. First Kings 1:33 mentions Solomon riding a donkey on the day he was recognized as the new king of Israel… The mention of a donkey in Zechariah 9:9-10 fits the description of a king who would be ‘righteous and having salvation, gentle.’ Rather than riding to conquer, this king would enter in peace.” (gotquestions.org, “Why would A King Ride A Donkey Instead Of A Warhorse?”

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A very large crowd spread their cloaks on the road, while others cut branches from the trees and spread them on the road. The crowds (of disciples) that went ahead of him and those that followed shouted,

“Hosanna to the Son of David! Blessed is he who comes in the name of the Lord! Hosanna in the highest heaven! Peace in heaven and glory in the highest!”

Some of the Pharisees in the crowd said to Jesus, “Teacher, rebuke your disciples!”0 “I tell you,” he replied, “if they keep quiet, the stones will cry out.”

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Their chant is probably a reference to Psalm 118, which describes a king entering a city to ascend to the altar and offer sacrifice: “Bind the festal procession with branches, up to the horns of the altar!" (Psalm 118:27). This time, the king is the sacrifice.

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When Jerusalem came into view, He looked intently at the city and began to weep.

Jesus: Oh, Jerusalem, how I wish you knew today what would bring peace! But you can’t see…”

Jesus used the phrase “what would bring peace” elsewhere.

“What king going to encounter another king in war will not sit down first and take counsel whether he is able with ten thousand to meet him who comes against him with twenty thousand? And if not, while the other is yet a great way off, he sends an embassy and asks terms of peace.” (Luke 14:31-32)

"Terms of peace" is the same phrase translated "what would bring peace." The king will bring peace, but it will be the King’s peace, on the King’s terms, and in the King’s way.

Then Jesus drives out the money lenders in the Temple
Then Jesus curses a leafy fig tree for not bearing fruit.
The he tells the chief priests and the elders that tax collectors and the prostitutes would the kingdom of God ahead of them before telling them the parable of a landowner with a vineyard who sent his son to collect the harvest, and the tenents killed him. “ “Therefore I tell you that the kingdom of God will be taken away from you and given to a people who will produce its fruit.”

It’s an interesting way for the Messiah to start his Kingship.

The crowds cheered him as The Messiah – and by that, they meant a zealot warrior who would overthrow Rome.[1] That’s why there were palm branches. It was the sign of the Zealots. They wanted bloodshed from a Messiah with a sword. I have to imagine they weren’t too excited about a King on a donkey instead of a war horse.

The religious leaders were looking for Temple messiah, one who would purify the Temple and restore its reputation and influence in the world.

Well, Jesus purified the Temple, but not in the way they expected. He overthrew the hypocrites in the temple, then demonstrated the uselessness of a tree that does not bear fruit it is meant to, and told the chief priests and elders that that tree was them: fruitless; barren. He goes on to tell them they actually made disciples on behalf of hell (Matthew 23:15).

He refused to start an uprising against Rome. He actually told people to give to Caesar what was Caesar’s, and to repay evil with good. He told them that his Kingdom was not of this world, so his followers shouldn’t use force to spread His kingdom.

To get an idea of just how unsettling this was, think of John the Baptizer, while in jail awaiting his death, sent a message to Jesus: “Are you the one who is to come, or should we expect someone else?” This was John the Baptist, who once announced Jesus as, “Behold the Lamb of God who takes away the sin of the world.” He needed to know if Jesus was the real deal.

Jesus replied by quoting Isaiah (35:5 and 61:1): “Go back and report to John what you have seen and heard: The blind receive sight, the lame walk, those who have leprosy are cleansed, the deaf hear, the dead are raised, and the good news is proclaimed to the poor. And blessed are those who do not take offense in me.” (Luke 7)

That last line seems odd, but remember that the Jews were expecting a Messiah with a sword, not just a healing touch. Jesus is basically saying, ‘Don’t let this trip you up. This is what a real Messiah does.”

“Oh, Jerusalem, how I wish you knew today what would bring peace! But you can’t see…”

So what is the peace the Messiah was bringing, and where do we see it?

It was Jesus, and we see it in Jesus.

“In Him we have redemption through His blood, the forgiveness of our trespasses, according to the riches of His grace.” (Ephesians 1:7)
“For this is My blood of the covenant, which is poured out for many for forgiveness of sins.” (Matthew 26:28)
“… and from Jesus Christ, the faithful witness, the firstborn of the dead, and the ruler of the kings of the earth To Him who loves us and released us from our sins by His blood…” (Revelation 1:5-6)
“How much more will the blood of Christ, who through the eternal Spirit offered Himself without blemish to God, cleanse your conscience from dead works to serve the living God?” (Hebrews 9:14)
“Therefore, being justified by faith, we have peace with God through our Lord, Jesus Christ.” (Romans 5:1)

I don’t know what you expect from Jesus, but let’s look at the life and mission of Jesus.

If you expect that peace will come to the world (and to you) when the King takes care of the things around you, you will be disappointed. He didn’t make the Romans go away; he told the people how He would help them live in the presence of Romans. He didn’t confront others in answer to the hopes and prayer of the Pharisees; he confronted them.

They wanted a Messiah who would set everyone else right, as if the problem was only around them rather in them. This is why they couldn't see it. They assumed that God needed to deal with others.

But the problem was them. They were the source of sin in the world. They were the ones for whom the Messiah had to come.

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And Jesus did just that, and He set the terms of peace: He came to make things right between sinful, fallen humanity and a holy God, and he would do it by paying the price of reconciliation. He would satisfy the requirements of a just God while showing the heart of a loving God.

“God did not, then, inflict pain on someone else, but rather on the Cross absorbed the pain, violence, and evil of the world into himself… this is a God who becomes human and offers his own lifeblood in order to honor moral justice and merciful love so that someday he can destroy all evil without destroying us.” (Tim Keller)

Justice must be served because God is just; to save just one of us, it would have cost him a crucifixion. This should always humble us, because it reminds us that we are more sinful than we want to admit.

But mercy must be offered because God is merciful. To save just one of us, Jesus was willing to do this. This should always encourage us, because it reminds us that God’s love for us is so much deeper than we can ever imagine.

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[1] A short list of Messianic Kings who had tried and failed:

Judas (of Galilee), Zealot, led revolt against Romans AD 6 (Acts 5)
Judas Maccabeus 160's BC, considered on par with David/Gideon. He entered Jerusalem at the head of an army, purified the temple. His reconstitution of the temple is the basis of Hanakuh. He destroyed altars to Ashdod, but was eventually killed in battle.
Menahem ben Judah, (grand)son of Judas the Galilean led a revolt against Agrippa II.
Simon bar Kokhba 135), founded a short-lived Jewish state that he ruled for 3 years before being defeated in the Second Jewish-Roman War. 580,000 Jewish people died. He went from Kokhba,“Son of a Star” (Numbers 24:17) to Kozeba, “Son of the Lie.”
Theudas (mentioned in Acts 5:36) died in AD 46. He claimed to be a Messiah, and led about 400 people to the Jordan River, where he said he would divide it to show his power. He didn't. He was stopped and executed.
The Anonymous Egyptian (Jew). 55, (an allusion to Moses), with 30,000 unarmed Jews doing The Exodus reenactment. He led them to the Mount of Olives, where he claimed he would command the walls around Jerusalem to fall. His group was massacred by Procurator Antonius Felix, and he was never seen again.