Jesus' triumphal entry into Jerusalem before his last Passover is recorded in Matthew 21 and Luke 19. It was a fulfilment of a prophesy given to Zechariah in 9:9. The liturgy for the Feast of Passover included the Hallel, what we call Psalms 113 - 118. Psalms 118:26 says: "Blessed is he that cometh in the name of the Lord." These were the joyous words shouted by the people as Jesus entered the gates of Jerusalem, and later the entire Psalm was sung by the apostles at the conclusion of the Last Supper.
Matthew 21:1 "Now when they drew near Jerusalem, and came to Bethphage, at the Mount of Olives, then Jesus sent two disciples, saying to them, “Go into the village opposite you, and immediately you will find a donkey tied, and a colt with her. Loose them and bring them to Me. And if anyone says anything to you, you shall say, ‘The Lord has need of them,’ and immediately he will send them.” All this was done that it might be fulfilled which was spoken by the prophet, saying: Tell the daughter of Zion ‘Behold, your King is coming to you! Lowly, and sitting on a donkey, a colt, the foal of a donkey.’” So the disciples went and did as Jesus commanded them. They brought the donkey and the colt, laid their clothes on them, and set Him on them. And a very great multitude spread their clothes on the road; others cut down branches from the trees and spread them on the road. Then the multitudes who went before and those who followed cried out, saying: “Hosanna to the Son of David! ‘Blessed is He who comes in the name of the Lord!’ Hosanna in the highest!” And when He had come into Jerusalem, all the city was moved, saying, “Who is this?” So the multitudes said, “This is Jesus, the prophet from Nazareth of Galilee.”
Jesus probably rode the colt through the Eastern Gate, the location of which is seen in the picture below. If that is the case, the path would have switched back and forth due to the steepness of the terrain. The original Eastern Gate was destroyed along with the rest of the city in 70 A.D, and in later years another was built above it. This second gate, which is the one we see today, was bricked up by Sulieman the Great in AD 1541 to prevent a Jewish Messiah from entering. Without being aware of it, he was fulfilling Ezekiel 44:1. "Then he brought me back the way of the gate of the outward sanctuary which looketh toward the east. Then said the Lord unto me; This gate shall be shut, it shall not be opened, and no man shall enter in by it; because the Lord, the God of Israel, hath entered in by it, therefore it shall be shut."
The Mount of Olives was where the High Priest, on the Day of Atonement, sacrificed for the sins of the people. "There were five gates to the Temple Mount .................. the Eastern Gate on which was portrayed the Palace of Shushan. Through this the High Priest that burned the [Red] Heifer, and the heifer, and all that aided him went forth to the Mount of Olives. .......... All the walls which were there were high, except the wall in the east, so that the priest who burned the heifer, standing on the top of the Mount of Olives, and directing himself to look, saw through the gateway of the sanctuary, at the time when he sprinkled the blood. (Mishnah, Middot 1.3)
From atop the Mount of Olives, the High Priest looked across the Kidron Valley into the Sanctuary when he sprinkled the blood
Luke 21:37 "And in the daytime he was teaching in the temple; and at night he went out, and abode in the mount that is called the mount of Olives." Jesus left the city every night through the Eastern Gate, seen in the top tower, wound his way down the Kidron Valley, and slept on the Mount of Olives.
This picture was taken from the Temple Mount, and it views toward the Mount of Olives. The low eastern wall is visible in the background.
Matthew 26:30 - "And when they had sung a hymn, they went out to the Mount of Olives. Then Jesus said to them, “All of you will be made to stumble because of Me this night, for it is written:‘I will strike the Shepherd,And the sheep of the flock will be scattered.’ But after I have been raised, I will go before you to Galilee.” Peter answered and said to Him, “Even if all are made to stumble because of You, I will never be made to stumble.” Jesus said to him, “Assuredly, I say to you that this night, before the rooster crows, you will deny Me three times.” Peter said to Him, “Even if I have to die with You, I will not deny You! And so said all the disciples. Then Jesus came with them to a place called Gethsemane, and said to the disciples, “Sit here while I go and pray over there.” And He took with Him Peter and the two sons of Zebedee, and He began to be sorrowful and deeply distressed. Then He said to them, “My soul is exceedingly sorrowful, even to death. Stay here and watch with Me.” He went a little farther and fell on His face, and prayed, saying, “O My Father, if it is possible, let this cup pass from Me; nevertheless, not as I will, but as You will."
Gethsamene and the Mount of Olives, as seen from below the Temple Mount and looking across Kidron
The Mount of Olives is the place where the Lord will appear the second time. Zechariah 14:1. "Behold, the day of the LORD cometh, and thy spoil shall be divided in the midst of thee. For I will gather all nations against Jerusalem to battle; and the city shall be taken, and the houses rifled, and the women ravished; and half of the city shall go forth into captivity; and the residue of the people shall not be cut off from the city. Then shall the LORD go forth, and fight against those nations, as when he fought in the day of battle. And his feet shall stand in that day upon the Mount of Olives, which is before Jerusalem on the east, and the Mount of Olives shall cleave in the midst thereof toward the east and toward the west, and there shall be a very great valley; and half of the mountain shall remove toward the north, and half of it toward the south."
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