Midras Amsal 18:23: Devarim Rabbah, Ein Yaakov (Glick Edition) & Sifrei Devarim

“I pleaded with the Lord” – this is what the verse said: “A poor person speaks with pleas, and a wealthy one responds harshly” (Proverbs 18:23). Rabbi Tanḥuma said: “A poor person speaks with pleas” – this is Moses, who came to his Creator with pleas. “And a wealthy one responds harshly” – the wealthy One of the world, namely the Holy One blessed be He. He answered him harshly, as it is stated: “Do not continue speaking to Me” (Deuteronomy 3:26).
Another matter: Rabbi Yoḥanan said: “A poor person speaks with pleas [taḥanunim]” (Proverbs 18:23) – these are the prophets of Israel. “And a wealthy one responds harshly” (Proverbs 18:23) – these are the prophets of the nations of the world. Rabbi Yoḥanan said: There was no one in the nations of the world more righteous than Job, and he came only with reproaches [tokhaḥot], as it is stated: “I would organize my case before Him and fill my mouth with arguments [tokhaḥot]” (Job 23:4). There were none greater among the prophets than Moses and Isaiah, and both of them came only with pleas. Isaiah said: “Lord, be gracious to us [ḥanenu] ; we have longed for You” (Isaiah 33:2), and Moses said: “I pleaded [va’etḥanan] with the Lord.”
Another matter: “I pleaded with the Lord” – to what is the matter comparable? To a noblewoman who bore a child.⁵Some interpret this to refer to a concubine of the king (see Midrash HaMevo’ar). In any event, the meaning is that because she bore a child to the king or ruler, she could enter the palace whenever she wanted. All the days that her son was alive, she would enter the palace with impunity. When her son died, she began asking to enter with pleas. So, as long as Israel was alive in the wilderness, Moses would enter before the Holy One blessed be He with impunity: “Lord, why will Your wrath be enflamed against Your people” (Exodus 32:11)? “Please pardon the iniquity of this people…” (Numbers 14:19). When Israel died in the wilderness,⁶This refers to the generation that had experienced the exodus from Egypt. he began asking to enter the Land of Israel with pleas – “I pleaded.”

R. Nachman said in the name of Rab: "What is the meaning of the passage (Prov. 18, 23) The poor speaketh entreatingly, but the rich answereth roughly. The poor speaketh, refers to Moses; and the rich, etc., refers to Joshua." What is the reason [for such an interpretation]? Shall I say because it is written (Josh. 6, 21) And he laid them out before the Lord? And R. Nachman explained this that he laid them down closely upon one another [and pleaded with Him], etc. Did not Pinchas do the same? As it is written (Ps. 106, 30) Then stood up Pinchas, etc. It ought to be written, va-yithpalel, which means, and he prayed, instead of va-ye phalel (debated). R. Elazar said: "Infer from this that he had debated with his Creator. He cast them before the Lord, saying: 'Sovereign of the Universe! were these so worthy that on account of them twenty-four thousand persons of Israel should fall? — as it is written (Num. 25, 9) And those that died in the plague were twenty and four thousand.'" And if you infer it from the passage (Josh. 7, 7) Wherefore hast Thou caused this people to pass over the Jordan?— did not Moses say similar to this (Ex. 5, 22) Wherefore hast thou let so much evil come upon this people? We must therefore say, because Joshua said (Jos. 7, 7) Would that we had been content, and dwelt on the other side of the Jordan. (Ib., ib. 10) And the Lord said unto Joshua: Get thee up. R. Shilla lectured: The Holy One, praised be He! said to him: "Thine [transgressions] is worse than theirs, for I have said (Deut. 27, 4) And it shall be as soon as ye are gone above the Jordan, that ye shall set up these stones, but ye went a distance of sixty miles before ye did this." After Shilla went away, Rab appointed an interpreter and lectured (Jos. 11. 15) As the Lord commanded Moses His servant, so did Moses command Joshua; and so did Joshua; he left nothing undone of all that the Lord commanded Moses. But why is it written, Get thee up? It means that the Lord said to him: Thou thyself hast caused all the evils, [because thou didst declare as accursed the goods of Jericho]. And this is meant by the passage (Ib. 8, 2) Only its spoil and its cattle shall ye take for booty unto yourselves.

(Devarim 3:23) "And I entreated the L-rd at that time, saying": This is as Scripture writes (Proverbs 18:23) "The poor man speaks imploringly and the rich one answers brazenly."