For the Jewish people, Passover was more than a religious observance. It was the time of year when they celebrated liberation from Egyptian bondage.
During Jesus' time, they also used this opportunity to express their longing for political freedom from Rome. Jews who claimed to be "messiahs" had so often caused riots during Passover that the Romans brought extra troops into Jerusalem during the Passover season. The Roman soldiers did not hesitate to shed blood to keep the peace.
Jesus on his way to Jerusalem
On the Sunday before Passover, Jesus came out of the wilderness on the eastern side of the Mount of Olives (just as the prophecy said the Messiah would come).
People spread cloaks and branches on the road before him. Then the disciples "began, joyfully, to praise God in loud voices for all the miracles they had seen" (Luke 19:37). The crowd began shouting, "Hosanna," a slogan of the ultra-nationalistic Zealots, which meant, "Please save us! Give us freedom! We're sick of these Romans!"
The Palm Branches
The people also waved palm branches, a symbol that had once been placed on Jewish coins when the Jewish nation was free. Thus the palm branches were not a symbol of peace and love, as Christians usually assume; they were a symbol of Jewish nationalism, an expression of the people's desire for political freedom.
Jesus as the Passover Lamb
Yet Jesus came to the people as the Lamb of God. Jesus, the sinless Messiah who would die on humankind's behalf, appeared on the very day that people chose their spotless Passover lambs!
It's almost as if God said to the world, "Here's my Lamb. Will you chose him?" But instead of turning to Jesus as the Lamb of God, the crowds misunderstood his proclamation that he was the Messiah. They wanted him to be their political-military deliverer.
In response, Jesus wept. The tears Jesus shed as the people cried out their political "Hosannas" were tears of grief for the hearts of his people.
Jesus foresaw the terrible devastation of Jerusalem that would result because the people did not recognize him as God's Messiah. The people were looking for a messiah who offered political deliverance and a political kingdom.
However they would have nothing to do with the Messiah who offered forgiveness and deliverance from sin. In his grief over their distorted beliefs, Jesus wept out loud.