Great is Repentance Before Prayer
It is written, “I implored the L-RD at that time, saying …” (Deuteronomy 3:23). Most of the commentators have questioned the meaning of the expression “at that time.” What time was that? They have explained that it consists of the time mentioned in the passage, “As for me, may my prayer to You, O L-RD, be at an opportune time” (Psalms 69:14). Moses asked that this moment be favorable in G-d’s eyes for accepting his prayer. Yet despite this, his prayer was not answered, for G-d had decided that he would not enter the Holy Land.
Regarding this subject, the book Beit Shemuel explains that “at that time” means the present moment, meaning that one shouldn’t think of the past or the future, but should only be concerned with the time in which he can correct his behavior. This is why Moses prayed when he could in order to implore G-d. Concerning this, I have heard that the word leimor (“saying”) alludes to the fact that a man’s prayer (as in the verse itself: “I implored”) should always be in his heart and mouth in order that he can say it (leimor) when he begins praying.
In my humble opinion, there is another way of explaining the expression “at that time” and leimor. Concerning this, the holy Reb Elimelech of Lizhensk states in his book Noam Elimelech: “When someone wants to perform a mitzvah, he should begin by repenting of the sins he has committed, for by his sins a man creates accusers and destructive angels (Perkei Avoth 4:13) that prevent him from subsequently elevating his mitzvot. Consequently, if there is no repentance, mitzvot cannot rise up.”
May I allow myself to add that not only do mitzvot not rise up in such a case, but that even the holiness that stems from them becomes the victim of the forces of impurity, which feed off of it. The Noam Elimelech affirms that we can remedy this situation by repenting before performing a mitzvah, for then we eliminate all accusers and destroy them by repentance, to the extent that mitzvot can rise up and we bring satisfaction to our Creator.
Following the same line of reasoning, we may add that we should also repent before praying in order not to be disturbed by these angels and accusers that seek to nourish themselves from prayer. Thus our prayers will be received with favor. This is why the Sages said, “The early righteous ones prepared themselves for an hour before prayer” (Berachot 30b), for they were actually undertaking a self-evaluation in order to repent of their prior sins so that their prayer would be received with favor. In fact it is written, “Know before Whom you stand” (Berachot 28b), yet how can one stand before the King of kings while stained with sins, faults, transgressions, and evil thoughts? This is why, before praying, we should recall all our sins and take it upon ourselves to not fall back into them. And even if one is certain to have not committed any sin – even if a person is righteous to a fault – we know that G-d is extremely demanding with those who are close to Him (Yebamot 121b). If He were to make the holy Patriarchs pass before Him in judgment, even they would not emerge innocent, for He would rebuke them. For what would they be reprimanded? On details so minute that a man doesn’t even take note of them. Consequently, it is also good to repent of all our sins before praying.
This allows us to understand the connection between Parsha Devarim and Parsha Va’etchanan. At first, Moses reprimanded the Children of Israel for all their wicked deeds, and he also enjoined himself to repent, in particular for the incident in which he struck the rock twice with his staff (Numbers 20:11). Concerning that, Moses told the Children of Israel, “But the L-RD became angry with me because of you, and He did not listen to me” (Deuteronomy 3:26). Then, when he finished and reprimanded himself and repented, he began to pray and implore G-d (va’etchanan). When was this? It was “at that time” – when he repented and there were none of his accusers left. His prayer was continually in his mouth (leimor), and yet it was not granted.
Everything that we have seen up to now allows us to explain the rest of the passage: “Let me please cross and see the good land that is on the other side of the Jordan” (v. 25). The Vilna Gaon explains that if Moses had said, “Let me please cross and please see the good land” (saying “please” twice), as he had done in his prayer for Miriam his sister (“Please, L-RD, heal her please” [Numbers 12:13]), his prayer would have been granted, as it had been for Miriam. In such a case Moses would have entered into Eretz Israel and the land would never have been devastated. However the Holy One, blessed be He, immediately stopped Moses and said to him, “It is too much for you! Do not continue to speak to Me further about this matter” (Deuteronomy 3:26), meaning, “Do not say ‘please’ [na] a second time” (see Imrei HaGra). We see, therefore, that Moses had his prayer so ready in his mouth that if the Holy One, blessed be He, had not stopped him so as to Sanctify His Name in public, his prayer would have been granted.
From all this, we learn that we may continually pray and think that our prayers are being heard, yet this may not be true if we have not completely repented of our wicked deeds beforehand. This is why we recite, before praying, the passage concerning sacrifices (Shulchan Aruch Orah Haim, beginning of paragraph 48). This is a way for a man to offer himself as a sacrifice before G-d and to repent of all his sins before addressing Him. It is a good way to prepare for prayer, but a great amount of concentration is required for it to be considered as if he had really sacrificed himself, for according to the Ramban (see Leviticus 1:9), a sacrifice replaces a man. Thus all that is done to an animal should really have been performed on a man. When a person realizes this, he will certainly repent, humble himself, and become like a sacrifice before G-d.