After reminding the Israelites of events from the recent past, Moses revealed that even though God had told him he would not be leading them into Canaan, he continued to pray that God would change his mind. Moses said that he "pleaded with the Lord at that time." The Hebrew word for "pleaded," chanan, is a word for both asking for, and bestowing, grace or mercy. Moses knew God's merciful character, and so he continued to pray for mercy on this matter until God let him know that he should stop.
Moses was someone who had repeatedly received what he asked for from God. In a sermonette at Church of the Messiah on February 25, 2023, Frank Fenton noted that one Jewish tradition, based on using gematria with va'etchanan, the Hebew for "and I pleaded" in verse 23, said that Moses prayed 515 times before God told him to stop. According to this tradition, he said that he would be willing to go into the land as an animal if he could not do it as a human being. Joseph's bones were going to be carried into the land. Why couldn't Moses go too? Frank urged us to keep praying as well, acknowledging that we are completely in God's hands.
There are a number of examples of such prayers in the Bible (e,g, Psalm 123; Isa 33:2). Jesus' parable of the persistent widow (Luke 18:1-8) urges us to keep praying. At Gethsemane Jesus prayed one last time that his mission could be accomplished by some other means than the crucifixiom (Lk 22:41-42), even though he had come to Jerusalem for that purpose. In a sermon at Church of the Messiah on February 25, 2023, Kyle Kettering also urged us to plead for God's grace, even for things that seem impossible.
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