Jesus and His party left Jericho and headed up the steep Roman road to Jerusalem; Luke doesn’t provide as many details about this part of the trip as Matthew did, although he does discuss briefly the procurement of the colt. Luke does however, make it clear that most of the crowds Jesus encountered upon His arrival believed He was there as a king to seize power. Yet, Luke’s main focus is at the end of his account; it isn’t how the people reacted to Jesus, but instead it is about how Jesus reacted to Jerusalem:
As he approached Jerusalem and saw the city, he wept over it and said, “If you, even you, had only known on this day what would bring you peace—but now it is hidden from your eyes. The days will come upon you when your enemies will build an embankment against you and encircle you and hem you in on every side. They will dash you to the ground, you and the children within your walls. They will not leave one stone on another, because you did not recognize the time of God’s coming to you.” (19:41-44)
Try to imagine the scene: The crowds were welcoming Him as their king in full expectation that He is about to seize control of the city and restore the Nation to its ancient glory with the help of the armies of God. Jesus is astride the colt representing His divine kingship in His hour of triumph, and when He sees the city, He weeps. But these are not tears of joy, they are tears of mourning, for He knows as no one else does at that moment that Jerusalem’s disastrous fate is about to be sealed. To make matters even more tragic, He knows that the fate that is about to be sealed is utterly unnecessary.
In these verses, Jesus speaks of what will happen here to God’s beloved city, the city that symbolized God dwelling in the midst of His people, when Roman armies encircle it and impose one of history’s most brutal sieges culminating in the utter destruction of the city and its remaining inhabitants.
Jesus knows at that precise moment, that He is coming here to die for the sins of Mankind, that His death will be brought about by the leaders of Jerusalem who will reject Him as they had rejected the prophets of God before Him. Of course He also knew that His death will be in fulfillment of God’s plan of redemption. Yet even so, He also knew that the very leaders, who will have Him killed, will lead the vast majority of the people against Him after the resurrection… and to their destruction.
Is it any wonder that He wept?