Jesus' entrance into Jerusalem was planned. Jesus intended for people to see Him as a King who came in peace, as a fulfillment of the covenant promises of God. Yet, Jesus was not exactly the kind of king the people expected. He claimed creation would cry out with injustice if the people didn't celebrate Him as the King, yet He wasn't coming to destroy the Roman occupiers. He came and wept over Jerusalem knowing how many were going to reject Him as their true King and the cost they would pay because of it. Not the kind of Messiah they expected at all.
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