The triumphal entry is recorded in the four gospels. Although the four evangelists have their own peculiarities, they all agreed that the people welcomed Jesus as the king of Israel. In 2 Sam 6:14-16, David, girded with linen ephod, was dancing when he brought the ark of the Covenant to Jerusalem while the people of Israel where shouting with the sound of the trumpet. Jesus was not just the new David who entered Jerusalem this time but he was also the personification of the Covenant. Jesus did not dance like David but rode instead on a donkey that had never been ridden. It was the fulfillment of the prophecy of Zechariah 9:9 “Your king comes to you triumphant and victorious, humble and riding on a donkey, on a colt…”
When the people welcomed him as king, it was the only time that Jesus let himself be celebrated by the people. In fact according to Luke (19:39-40), when the Pharisees said to Jesus to stop his disciples, Jesus replied “I tell you, if these were silent, the stones would shout out.” The entrance of Jesus is not just about him being the King of Israel but also the coming of the Kingdom being himself the Kingdom-personified. We call this in Greek as auto-basileia. The hosanna and the benedictus by the people were sung before Jesus went to the cross.
According to John, Jerusalem was filled with people not just because of the festival of the Passover but because the people who witnessed the raising of Lazarus went to meet him (Jn. 12:17-18). Jesus’ popularity during that time made everyone wanting to see him in person.
The people although welcomed Jesus in great jubilation did not understand the meaning of the event. Even Jesus’ disciples did not understand it either as commented by John (12:16) because the fuller understanding will be made manifest in the light of Easter. Because of this lack of understanding, the people’s hosanna and benedictus will later be turned into angry cries that long for Jesus’ death: “Crucify him!”
The triumphal entry was like a homecoming of a hero just like in our times. True enough, it was the homecoming of Jesus to the city which had suffered so much pain and witnessed enough blood shed. We can see it as Jesus’ way of conquering Jerusalem which will later reject him and throw him out to be crucified outside the city walls. The conquer was not through might and power but pain and suffering being represented by the donkey he was riding on which was a beast of burden.
The entry to Jerusalem was Jesus’ entry to his own death as a consequence of his "yes' to the Father. This all happened during the Passover Festival when the lambs were being offered in the temple in Jerusalem. The irony was that Jesus as the Lamb of God will be offered not in the temple but in Golgotha, the mountain of skulls. Indeed the triumphal feeling given by the people was short lived because the true triumph is not to be found in the temple sacrifice but on the sacrifice of the cross; the true triumph is not in Jerusalem the earthly city but in the heavenly Jerusalem. That is why Jesus died outside Jerusalem.
When we say "yes" to follow Jesus, we will follow him even if it means entering Jerusalem with him.