What does Luke 19:44 mean?
Jesus is on a donkey, riding into Jerusalem. The crowd around Him chants that the kingdom of David has come (Luke 19:28–40). Instead of celebrating, when Jesus sees Jerusalem, He weeps. He knows the leadership of the Jews will not accept their King and Messiah. They will fail in their responsibility to lead their people to salvation. And so, they will forfeit their city and their temple.Within forty years of Jesus' earthly ministry, the next generation of Jewish leaders will have a hand in Jerusalem's destruction. There will be so much infighting that when the Roman leader Vespasian finally sees a clear route to take his army to Jerusalem, he waits. Jewish political differences have turned violent, and Vespasian is willing to watch them wear themselves out.
When Vespasian returned to Rome to become emperor, his son Titus followed his father's lead. It's difficult to say what might have happened had the Jewish leaders set aside their differences earlier and fought against Rome together. In the end, the Jews made a valiant effort, and it took the Roman army longer than they expected to take the city. As they finally breeched the eastern wall, the Romans stole the coins and some of the implements in the temple, then set the building on fire. What metal the Romans didn't easily extract melted into the seams of the stone floor. When the soldiers realized it, they tore apart the temple, stone by stone, and scraped the gold and silver from the cracks.
The in-fighting between the Jewish factions probably resulted in many unnecessary deaths. Titus besieged Jerusalem during Passover, one of the three yearly feasts that filled Jerusalem with travelers. When Jews tried to flee Jerusalem and evade the Romans, they were caught and crucified. Some accounts indicate five hundred a day died this way. More than one hundred thousand died of starvation. Over the span of the entire war, nearly as many Jews were captured; the Romans forced some to become gladiators, enslaved many, and burned others alive.
Jesus sees the future: siege works, mass graves, and starving people. Even more, He sees the hundreds of thousands of Jews who will come for the Passover and spend eternity in torment because their leaders will give into envy, refuse to see how He fulfills the prophecy of the Messiah, and lead their people away from their God.
Luke 19:41–44 records the scene as Jesus weeps over Jerusalem. He is on a donkey, riding toward the city. Soon, He will be mocked, beaten, humiliated, and crucified. Right now, however, He looks over the mighty walls and thinks about the city that holds the temple of God. The people there—the nation—will not accept Him as their Messiah. Then, in AD 70, Romans tear down the very stones. In the next passages, Jesus cleans out the temple and the Sanhedrin plot against Him, parallelling the conditions that will bring Jerusalem's destruction. Both Luke and Matthew record Jesus similarly lamenting over Jerusalem (Luke 13:31–35; Matthew 23:37–39). But Luke is the only Gospel writer to include this depiction of Jesus weeping over Jerusalem and its future.
Jesus approaches Jerusalem by way of Jericho. Along the road, he encounters Zacchaeus: an unusually short man and infamous tax collector. Zacchaeus responds to Jesus' invitation and demonstrates humility and repentance. Jesus gives a parable explaining a believer's obligation to encourage the spread of the gospel. Jesus enters Jerusalem to great fanfare, upsetting local Pharisees. As He rides, Jesus weeps to think of the future destruction in store for the city. He once again drives corrupt businessmen from the temple grounds. His enemies are furious, but too afraid of the adoring crowds to take direct action.