What does Luke 19:41 mean?

Jesus is in the middle of His triumphal entry into Jerusalem (Luke 19:28–40; Matthew 21:1–11; Mark 11:1–11; John 12:12–16). He is riding a donkey in fulfillment of Zechariah 9:9. The road is lined with cloaks and palm fronds. The people around Him are celebrating the arrival of David's promised heir. They are going to celebrate the Passover, a feast in honor of God's miraculous rescue of the Israelites from their captivity in Egypt.

And Jesus is weeping.

The Pharisees have set the scene better than the multitudes of Jesus' disciples. They told Jesus, "Teacher, rebuke your disciples" (Luke 19:39). In this moment, they represent the Jewish leadership who will not follow the crowds in welcoming Jesus' arrival. They will reject their King and Messiah and manipulate the Roman governor to crucify Him.

The people are rejoicing, shouting, "Peace in heaven and glory in the highest!" (Luke 19:38). Jesus laments, saying, "Would that you, even you, had known on this day the things that make for peace! But now they are hidden from your eyes" (Luke 19:42). The Jewish leadership refuse to see who Jesus is. And so, after He is crucified and resurrected—which must happen no matter what—the priests and elders will not take their rightful place as leaders in spreading the worship of Jesus and salvation through grace to the Jews and then to the Gentiles (Genesis 12:1–3). Jerusalem will stand just long enough for Christianity to gain a toehold in Gentile countries, and then Rome will destroy the city and the temple (Luke 19:43–44).