The Tragic Entry of Jesus into Jerusalem in Luke 19:28–44

Jesus’ entry into Jerusalem before he was crucified is often called the triumphal entry, but how triumphal was it? Luke’s account of Jesus’ entry in Luke 19:28–44 (in comparison to the synoptic accounts in Matt 21:1–11; Mark 11:1–11) emphasizes an element of tragedy in this event.

Luke begins his account of Jesus’ entry into Jerusalem with the words after he said this (Luke 19:28). This wording ties Jesus’ entry into Jerusalem closely in with what has preceded in the narrative, which is the parable of the ten pounds (Luke 19:11–27). Luke states in Luke 29:11 that Jesus told this parable because he was about to enter Jerusalem, and some of his disciples had mistakenly thought that the kingdom of God was about appear immediately.

Jesus understood God’s plan better than his disciples did. Jesus’ entry into Jerusalem marks the end of a long journey during which he had been purposely on his way to Jerusalem. In Luke 9:51, after Peter’s declaration about Jesus being the Christ and Jesus’ foretelling his death for the second time to his disciples, Luke states that Jesus “set his face to go to Jerusalem.” In Luke 13:33 Jesus is recorded as saying to the Pharisees that he had to keep going on his journey because it was not possible that “a prophet die outside Jerusalem.” In Luke 18:31 Jesus takes the twelve apostles aside and tells them for the third time that he was going to die, but for the first time he pointed out specifically that his death would take place in Jerusalem.

In Luke’s narrative, Jesus had already told his disciples that dark clouds awaited his arrival in Jerusalem, but his disciples did not seem to have been able to comprehend how the Messiah could die. They were expecting a triumphal entry of the Messiah into Jerusalem.

This expectation of triumph is highlighted in Luke’s narrative. On reaching Jericho, some 22 kilometers from his final destination, Jesus healed the blind beggar, and people started praising God for the miraculous healing that Jesus had performed (Luke 18:35–43). It was this large crowd that caused Zacchaeus to climb the tree (Luke 19:1–10). The scene was one of jubilant disciples going up to Jerusalem. It is very interesting, however, that the person most eager to get there was none other than Jesus himself. He was leading the pack (Luke 19:28).

As the countdown continued, Jerusalem was getting ever closer. They reached the villages of Bethphage and Bethany, less than three kilometers from Jerusalem, so Jesus sent out two of his disciples to get a young male donkey. This detail emphasizes that Jesus came in fulfillment of God’s plan. Jesus knew that everything would happen just as God had revealed it in the Old Testament Scriptures. Luke 19:30–34 stresses how Jesus was in command of the situation. Everything was prepared. The colt upon which no one had yet ridden was there, ready for its spot in the limelight.

Luke assumes his readers know the significance of this detail about the donkey. It all goes back to the prophecy of Zech 9:9, which says: “Rejoice greatly, O daughter of Zion, shout in triumph, O daughter of Jerusalem! Behold, your king is coming to you; he is victorious and endowed with salvation, humble and mounted on a donkey, even on a colt, the foal of a donkey.” Jesus knew that this prophecy applied to him, and so he knew that a donkey would be ready. The disciples who had been sent on the donkey mission found everything exactly as Jesus had said it would be (Luke 19:32). Everything was ready. The Scriptures must be fulfilled.

After the donkey was brought back to Jesus, the disciples in question threw their cloaks upon the colt’s back to form a humble saddle, and they helped Jesus sit on the donkey (Luke 19:35). As he was riding into Jerusalem, the crowd were spreading their cloaks out before his path to form the equivalent of a humble red carpet, acknowledging Jesus’ royalty (Luke 19:36). The crowd may have been slow to understand many things about Jesus, but this time they were spot on about one thing: this was the promised king of Zech 9:9. The prophecy commanded: “Shout in triumph, O inhabitants of Jerusalem!” And this is what they were doing. The King had come in fulfillment of Scripture.

Drawing ever closer to the city, as Jesus reached the descent of the Mount of Olives, the whole crowd of disciples were rejoicing and praising God for all the miracles that they had seen Jesus perform. Luke emphasizes the emotional condition of the disciples in Luke 19:37. Literally, they “began to praise God with a load voice, rejoicing.” The crowd was praising, shouting, rejoicing. The key content of their acclamation was taken from the victory hymn Ps 118: “Blessed is the King who comes in the name of the Lord”(Ps 118:26); to which they added the words of praise: “peace in heaven and glory in the highest heaven!”

This is what the Jews had been waiting for. The Messiah, the second King David, who would save Israel from her enemies, had come! After so many years of humiliation and defeat at the hands of the Assyrians, the Babylonians, the Medes and Persians, the Greeks, and then the Romans, finally the King had come. The people of Israel had been waiting for this for so long. For over a thousand years they had been waiting for the true Davidic King to arrive. And now it had come to pass.

This was the time of the fulfillment of prophecies like Zech 2:10 –12, which reads: “Sing for joy and be glad, O daughter of Zion; for behold I am coming, and I will dwell in your midst, declares the Lord … and the Lord will possess Judah as his portion in the holy land, and will again choose Jerusalem.” Some 550 years after that prophecy was made, the Lord, Israel’s God, was coming to dwell in the midst of his people through the agency of Jesus, the Messiah. The focal point of world history, when the promised Savior King came to reign in Jerusalem, the capital city of God’s kingdom on earth, had arrived. God’s messianic promises were being fulfilled before their very eyes. The dream had come true!

All of this meant that this was rightfully to be the party time of the millennia. But in the midst of such rejoicing, what Luke records in Luke 19:37 presents a truy discordant note. Some of the Pharisees in the crowd said to Jesus: “Teacher, rebuke your disciples!”

The Pharisees come across here as being massive party poopers. It is bad enough being a party pooper, but here the Pharisees showed themselves as being party poopers at the party of all parties. That takes some hide, or at least a great hardness of heart. The stubbornness of the Pharisees to praise God because of the coming of kingdom of God into the world through Jesus stands in great contrast with the enthusiastic joy of the crowd.

How painful it must have been to Jesus to see such an attitude (even though he knew it had to be that way). Jesus replied to the Pharisees: “If the crowd were to become silent, then the stones would cry out!” (Luke 19:40). There is great irony here. The Pharisees, the respected religious leaders of the people, were more brain-dead than a pile of inanimate rocks!

This was seriously saddening, and Jesus entered into the sadness of what this kind of attitude would mean for the Jews as a whole. As he drew closer, seeing the city, his beloved Jerusalem across the Kidron Valley, he broke up and wept for the city. Amidst the bitter tears, he muttered the words:

If only you knew this day what would bring you peace! But now it is hidden from your eyes. For the days will come upon you when your enemies will throw up a barricade against you and surround you and hem you in from all sides, and raze you and your children within you to the ground, and they will not leave one stone upon another within you, because you did not recognize the time of God’s coming to you (Luke 19:42–44).

According to Luke, Jesus viewed his coming as God’s coming to Israel. This was a momentous occasion, an event of supreme significance; but many did not recognize it for what it was … to their own destruction. From Jesus’ perspective, this was terribly sad.

All in all Luke draws for us an amazing and moving picture: from the exuberant joy of the crowd at this historic moment to Jesus’ tears at the hardness of people’s hearts. The triumphant joy all too soon turned to tragic sorrow. It is for those reasons that the triumphal entry, the way Luke paints it, might better be known as the tragic entry of Jesus into Jerusalem.