While escorting Jesus to his home, Zaccheus is overcome by the power of the Holy Spirit and born again through repentance and faith. As they stand in the street, they are surrounded by a great crowd of disciples and onlookers. According to the ancient Roman historian Josephus, approximately two million pilgrims would flood into Jerusalem to celebrate Passover, so the crowds must have been enormous. In this atmosphere the religious excitement is high. Every miracle Jesus does adds to the growing conviction that He is indeed their Messiah and that when He arrives in the capital city, He will begin a revolution to free them from Rome's bondage, like Moses freed them from Egypt's. Unfortunately, in spite of all that Jesus has said earlier (Lk 9:22,44; 18:31-34), even His disciples are caught up in this misguided fervor. So He addresses a parable to them which is intended to correct their thinking so that when He does come to judge the earth, they will not be ashamed.

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