Jesus descended from the Mount of Olives on the donkey and rode up into the city on the east side of Jerusalem. He entered in four days before the Passover. This is the day of preparation when the Passover lamb is chosen. The father of each Jewish family would find a lamb and present it for acceptance; it had to be perfect and without blemish. Even so, the Father was bringing his Lamb to the Jews for acceptance and the crowd shouted Hosanna! Mat 21:9
Pilate was also most likely entering Jerusalem on the west side from Caesarea. He came each year with his crack troops to keep the Jews under control on this sacred and national day! He would always come up a few days before Passover with his army on powerful horses. It was a great show of human strength and glory. The man on a horse versus the man on the donkey!
Hosanna was not a religious term but originally a political term which meant deliver us from oppression. And if the people were crying out “Hosanna,” it could only mean deliver us from Roman oppression. When the high priests heard the crowd shouting Hosanna they said to be quiet for fear that Pilate would hear and serious trouble would ensue. “But when the high priests and the scribes saw the amazing things that he had done and the children shouting in the Temple, “Hosanna to the Son of David,” they became furious (Mat 21:16).
They needn’t have worried; Jesus prevailed over the kingdom of men. The kingdom represented by the man on the horse lasted another hundred years. The kingdom of the man on the ass has lasted 2000 years and will never end. The scripture the Jews had in mind as they shouted hosanna, shows us why they were so happy and expectant.
Be full of joy, O daughter of Jerusalem: see, your king comes to you: he is upright and has overcome; gentle and seated on an ass. And he will have the war-carriage cut off from Ephraim, and the horse from Jerusalem, and the bow of war will be cut off: and he will say words of peace to the nations: and his rule will be from sea to sea, and from the River to the ends of the earth. And as for you, because of the blood of your covenant, I have sent out your prisoners from the deep pit in which there is no water. Zech 9:9-11
This was a clear prophecy that the King on the donkey was going to defeat the horses of the Roman oppressors and set up a kingdom that would reach from sea to sea.
Friends, I’m glad His kingly rule reached even me and I’m glad that two thousand years later He is still sending prisoners out of the deep pit in which there is no water (Hell) for I was one. How about you?