Summary: Jesus, the Passover Lamb, heads into Jerusalem, where He initiates a massive public demonstration as He offers Himself to be King of Israel. This event is the inauguration of the Prince of Peace as King of kings.
THE TRIUMPHAL ENTRY
During Passover time, Jerusalem was crowded with visitors. Every Jewish adult from a twenty mile radius was obligated to attend the celebrations, and this number was added to by many, many more who would crowd in from further a field for the occasion. William Barclay tells us that the city was teeming with people, as many as two and a half million might have been in Jerusalem [Barclay, The Gospel of Matthew, vol. 1. P. 262]. They were there to commemorate Passover, an event that had taken place fifteen hundred years earlier…when God delivered His people from the land of bondage in order to lead them to the Promised Land.
The Triumphal Entry, as it is called, occurred on Sunday of Passion week. It is one of the events that all four Gospels record giving the occasion great significance. Jesus, the Passover Lamb, heads into Jerusalem [for the last time], where He initiates a massive public demonstration as He offers Himself to be King of Israel (CIT). Keep in mind that normally Jesus moved quietly and preferred obscurity, many times charging those He healed to “tell no man” (Mt. 8:4). Here, however, He sets in motion a huge crusade. Why? It probably was so the Jews would never be able to say, “If we had only had the opportunity to embrace You as our King, we certainly would have done so.” He stripped away that excuse from the Jewish nation when He rode into Jerusalem and publicly offered Himself to them as their Messiah.
This passages emphasizes that Jesus is the King of Glory: the King comes in peace (21:1-5); the King is acclaimed by the people; and the King is crowned with praise. This event is the inauguration of the Prince of Peace as King of kings.
I. THE KING COMES IN PEACE, 21:1-5.
II. THE KING IS ACCLAIMED BY THE PEOPLE, 21:6-8.
III. THE KING IS CROWNED WITH PRAISE, 9-11.
Jesus’ coming into Jerusalem is a climax for which anticipation has been building. Ever since the disciples had identified Jesus as ‘the Christ, the Son of the Living God’ at Caesarea Philippi (16:16), Jesus can then state that, ‘He must go to Jerusalem’ (16:21). Now He arrives. Not only is the place itself significant, but His arrival at the time of the Passover festival is significant, for the Passover was itself a clear foreshadowing of His own death as the Passover Lamb. John the Baptist introduced Jesus to the world as, ‘the Lamb of God, who takes away the sin of the world’ (John 1:29). It is significance that Jesus Christ was proclaimed to the world as God’s Passover Lamb by God’s chosen herald.
Matthew’s account of the Triumphal Entry begins with Jesus sending two disciples in verse 1. “When they had approached Jerusalem and had come to Bethphage, at the Mount of Olives, then Jesus sent two disciples,
[They crossed the Jordan and traveled south through Perea to avoid Samaria which brought them through Jericho. The distance from Jericho to Jerusalem is about seventeen miles, or fifteen miles to Bethany; the difference in elevation is some three thousand feet. Matthew does not mention the arrival at Bethany, which John describes as occurring "six days before the Passover" (John 12:1), probably on Friday afternoon.]
Jesus and His disciples had come to Bethphage, [“house of figs,”] from the east as they came up the road from Jericho. The town is on the slopes of the Mount of Olives, a two and a half mile long ridge, laying two miles directly east of Jerusalem. When one comes from the east to the top of the Mount of Olives, the panorama of Jerusalem just across the Kidron Valley to the west is magnificent.
It appears that Jesus stayed at the home of Mary, Martha, and Lazarus for several days including the Sabbath. He initiates His final week by sending two of His disciples ahead into a village [possibly Bethany -Mk. 11:1] to find a donkey with a colt, and to bring the animals to Him.
[The Mount of Olives, (Mt. 24:3, 26:30,36 Zec 14:4) in Acts 1:12 'Olivet,' is a low mountain or long and lofty hill, which begins north of Jerusalem and runs eastward, and then turning at a point nearly a mile northeast of the city, runs southward until interrupted by the outlet of the valleys which lie east and south of the city, and send off their united streams at the southeast in a deep ravine towards the Dead Sea. The mountain evidently took its name from its fruitfulness in olives. The valley which separates it from Jerusalem is “the brook Kidron” in John 18:1.]
Jesus sent His disciples ahead to made preparation for His prophetic entrance into Jerusalem in verses 2 & 3. “saying to them, “Go into the village opposite you, and immediately you will find a donkey tied there and a colt with her; untie them and bring them to Me.  “If anyone says anything to you, you shall say, ‘The Lord has need of them,’ and immediately he will send them.”