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וָאֶתְחַנַּ֖ן אֶל־יְהוָ֑ה בָּעֵ֥ת הַהִ֖וא לֵאמֹֽר׃

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Rashi on Deuteronomy

ואתחנן — All forms of the verb חנן signify an ex gratia gift. Although the righteous might make a claim to reward depend Upon their good deeds, yet they solicit from the Omnipresent only an ex gratia gift. [Because He had said to him, (Exodus 33:19) “I will show grace (וחנתי) unto him to whom I will show grace”, he (Moses) when referring to his entreaty of God uses the expression (lit., spoke to Him) "I implored grace (ואתחנן)” (Midrash Tanchuma 5:2:3] — Another explanation is that the idea of an ex gratia gift is not to be stressed; but this is merely one of the ten terms by which prayer is described, as are enumerated in Sifrei Devarim 26:7.
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Ramban on Deuteronomy

AND I BESOUGHT THE ETERNAL AT THAT TIME, SAYING. [The time referred to, is] when Moses mentioned the conquest of the lands of Sihon and Og. He said, And I commanded Joshua at that time,1Above 3:21. intimating, that “I [Moses] will not go over there, for I besought the Glorious Name2Further, 28:58. [to rescind the decree forbidding me to enter the Land], but He hearkened not to me and He commanded me to charge Joshua, for he shall go over before this people.”3Verse 28 here.
The purport of the expression at that time is that it alludes to the time of the decree that he mentioned, Also the Eternal was angry with me [for your sakes, saying: ‘Thou shalt not go in thither’],4Above, 2:37. though [Moses’] supplication is not mentioned there on the day of that event. The correct interpretation, however, is that the expression at that time refers to the time mentioned: “when I conquered Sihon and Og and I began to war against the nations given to Israel and I allocated the land to the two tribes [Reuben and Gad].” In that case, this supplication [referred to here] was offered when it was said to Moses, Get thee up into this mountain of A barim,5Numbers 27:12. for it was then that he sought mercy in the matter and entreated this supplication. And when G-d did not hearken to his voice, he again prayed, Let the Eternal, the G-d of the spirits of all flesh, set a man over the congregation,6Ibid., Verse 16. as is mentioned there. It is this verse, And charge Joshua3Verse 28 here. [that constitutes the answer to Moses’ second request]. Now, there [in the Book of Numbers] Scripture mentioned the prayer on which he was affirmatively answered [namely, the appointment of a successor]7Ibid., Verses 18-21. and here he mentioned this [unsuccessful prayer] in order to inform the people that, although the Land was beloved to him, he did not merit [to enter] it because of them. All this was part of his reproof.
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Kli Yakar on Deuteronomy

I pleaded to Hashem. Rashi explains that even though the righteous can claim rewards based on their good deeds, they ask the Almighty only for an undeserved gift. This is difficult to understand, for why would one think that they would ask for reward based on the good deeds that they had already performed? A person can never have any claim that Hashem owes him, because all of the mitzvot that a person does can never be sufficient to pay Hashem back for all the goodness that He does…
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Kitzur Baal HaTurim on Deuteronomy

23:1 וָאֶתְחַנַן – I Prayed. Written (in the verse) before (vs22) is, לֹא תִירָאוּם, You shall not fear them (3:22). (Moses thought to himself) “I encouraged Israel. Perhaps He will have mercy upon me”
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Or HaChaim on Deuteronomy

ואתחנן אל ה׳ בעת ההיא לאמור, "I pleaded with G'd at that time, saying, etc." Why did Moses have to say "at that time?" Sifri writes that when Moses saw how Sichon and Og had fallen, he believed that the fact that he had lived to see this was proof that G'd had relented in His decree against him and that this was an opportune time to plead to be allowed to enter the West Bank. If we accept this interpretation the words בעת ההיא refer to the time of the wars with Sichon and Og. Moses excused himself saying that had it not been for what he had been allowed to witness at that time he would not have pleaded for G'd to rescind His decision seeing he was aware that the decree was final.
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Tur HaArokh

ואתחנן, “I pleaded;” Nachmanides writes that when Moses mentioned the conquest of the lands of Sichon and Og, (3,21) adding the words ואת יהושע צויתי וגו', “and I commanded Joshua” (in preparation for his becoming his successor) it was because he wanted to stress that he himself was not going to cross the Jordan. He now added the reason why he felt sure about this, namely that he had already pleaded with Hashem to allow him to at least cross that river, but his plea had not been accepted. It was therefore his duty to pray to Hashem to give Joshua the strength without which no one could successfully lead the Jewish people.
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Siftei Chakhamim

The word חנון everywhere signifies, etc. Otherwise, it should have said ואתפלל (I prayed).
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Rav Hirsch on Torah

V. 23. חנן .אתחנן (siehe Bereschit 6, 8). חנן: gewähren, חן Gewährungswürdigkeit, חַנֵן nur Prov. 26, 25 Gewährung suchen. התחנן entweder: sich (lat.) Gewährung suchen, oder (accus.) sich gewährungswürdig zu machen suchen. Die Konstruktion mit אל spricht für das letzte. Es ist eine reflexive Einwirkung auf das eigene Innere, es in Beziehung zu Gott seines gewährenden Wohlwollens würdig zu machen. So wird auch Berachoth 30 b aus dem Begriffe התחנן die Aufgabe für den zum Gebete Schreitenden gefasst, sich also vorher in seinem Innern zu sammeln, כדי שתתחונן דעתו עליו, dass sein Sinn die entsprechende Stimmung gewinne. בעת ההיא (siehe Bamidbar 27, 12).
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Daat Zkenim on Deuteronomy

'ואתחנן אל ה, “I pleaded with the Lord. The holy tongue knows of seven different names, each referring to a different category of prayer. They are as follows: תפלה, תחינה, נפילה, פגיעה, רנה, צעקה, זעקה. Of all the types of prayer at the disposal of Moses, why did he choose only one category, i.e. תחינה? When Moses had asked G–d to reveal more of His attributes, especially His method of dealing with sinners, in Exodus 33,13, after answering Moses in part, He had concluded with: וחנותי את אשר אחון, (verse 19 there) He made it clear to Moses that whenever and howsoever He forgives a sinner or reduces the punishment for which that sinner is in line, it is a gift a תחינה. It is not something that the recipient had a claim to. Moses wanted G'd to know that though he pleads, he is aware that even if G–d responds favourably to his plea, he will never forget that this would be an outright gift rather than something he had been entitled to. Letting him cross the Jordan would be an outright gift. (Compare Tanchuma, section three on our parshah). Another reason for Moses’ choice of the word: ואתחנן, is that the numerical value of the letters in that word וחנותי we quoted from Exodus 33,19, is the same as that of ואתחנן.
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Chizkuni

ואתחנן, “I pleaded;” the root חנן when used in the reflexive conjugation occurs in this sense also in Genesis 42,21 when Joseph is described as pleading with his brothers. According to Rashi, who considers the root of the word to be חנם, the final letter ן at the end, should really have been a final ם.
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Alshich on Torah

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Rashi on Deuteronomy

בעת ההוא [I IMPLORED GRACE OF GOD] AT THAT TIME — After I had subdued the land of Sihon and Og I thought that perhaps the vow that I should not enter the land was annulled, since this was part of the land of Canaan (cf. Sifrei Devarim 26:8 and Rashi on Numbers 27:12).
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Kli Yakar on Deuteronomy

The answer to this question is that when it says that the righteous can claim based on their good deeds it does not refer to those good deeds that they have already performed, but to those good deeds that they will do in the future. For it is understood that no righteous person wants to claim any physical benefit, except in order to be able to fulfill another mitzva… If so, Moshe could have based his request on those good deeds that he would do in the future if Hashem would grant him his request. This is something real.
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Kitzur Baal HaTurim on Deuteronomy

23:2 וָאֶתְחַנַן -- I Prayed. The gematria of this word equals שִׁירָה (song). Moses recited songs before HaShem, so that He would accept his prayers. The phrase הי אֱלֹהֵיכֶם, HaShem your God (vs22) is juxtaposed with וָאֶתְחַנַן to indicate (Moses meant) שִׁוִיתִי הי לְנֶגְדִי תָמִיד, I have set HaShem before me constantly (Tehillim 16:8).
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Tur HaArokh

בעת ההיא, “at that time;” at the time when the decree that he himself would not cross the Jordan had become final and irrevocable. He had not made mention of his plea on the day it had been rejected. Rashi explains the words בעת ההיא as the period during which the armies of Sichon and Og were crushed and their lands conquered. When G’d had not accepted his prayer, Moses tried once more, including the request to appoint a suitable successor for himself. This was the prayer that he alludes to here, i.e. a prayer that had been well received by Hashem. In other words, only the opening words of our paragraph ואתחנן אל ה' are a reference to his plea on his own behalf. The only reason he made a public reference to his personal plea at all was to let the people know that he valued the merit of being allowed to set foot in that land so highly that he even had asked to revoke the decree that denied him entry, even as a private. He hinted that his not being allowed to enter that land was (at least partially) the people’s fault.
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Siftei Chakhamim

Because [the Almighty] had said to him, etc. Rashi is saying: How did Moshe know to ask the Almighty even for an underserved gift, one that is not dependent upon good deeds? On this question Rashi explains, “I will be gracious, etc.”
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Or HaChaim on Deuteronomy

According to the sages in the Sifri even the word לאמור is part of Moses' plea. Moses challenged G'd to tell him if He was prepared to let him enter the Holy Land. I believe that all these comments are merely homiletics. The words בעת ההיא refer to the time when G'd had sworn that except for Joshua and Calev no one who had been over 20 at the time of the Exodus would see the land of Israel. Moses had referred to that date in 1,37 when he had mentioned that G'd had been angry at him also, saying that he too would not get to the Holy Land. At that time Moses had pleaded to cancel His decree and to release Himself from the oath as alluded to by the words: "You have begun to show your servant Your greatness, etc." Our sages interpreted these words as a reference to an invalidation of an oath, as I shall discuss shortly. The reason Moses inserted this paragraph at this point was so that the people should not suspect him of having pleaded only on his own behalf and that he was not concerned with G'd cancelling the decree He had sworn concerning the entire generation. By saying בעת ההיא, Moses indicated that he prayed before the decree had begun to be executed.
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Rashi on Deuteronomy

לאמר TO SAY (i.e. that God should say) — This is one of the three occasions where Moses spoke before the Omnipresent: I will not let You go until You tell me whether You will fulfill my request or not (Sifrei Devarim 26:9; cf. Rashi on Numbers 12:13).
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Rabbeinu Bahya

ואתחנן אל ה' בעת ההיא לאמור, “I pleaded with the Lord at that time, saying:” the words בעת ההיא, “at that time,” refer to the aftermath of the defeat of Sichon and Og, whose lands were given to the Israelites. At that time Moses had dared hope that maybe the decree that he would not be allowed to enter the Holy Land had been canceled. This verse is a continuation of verse 21 when the Torah mentioned ”these two kings.”
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Siftei Chakhamim

There is another explanation: This is one of the ten terms. According to the first explanation there is a difficulty: Why is it not written ואתחנם (I asked for a free gift). Therefore Rashi says, “There is another explanation, etc.” But according to the second explanation there is a difficulty: Why does it not say ויחל (implored) as above (Shmos 32:11).
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Or HaChaim on Deuteronomy

Even though we do not find in Moses' opening words that he prayed also on behalf of his people, his intention had been to pray on behalf of the people as soon as G'd had hearkened to his own prayer concerning himself. This would be relatively simple as we have a principle that once part of a vow has been cancelled, the entire vow is no longer valid (Nedarim 66). The word לאמור in our verse indicates that Moses was concerned not only with himself but also with additional words he was going to say. He thought he acted wisely as he assumed that it would be easier to obtain a cancellation of the part of the decree which referred to him personally not entering the Holy Land. After all, he, personally, had not committed a sin involving lack of faith as had his peers. All of Moses' words demonstrate that he considered G'd as having acted righteously.
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Rabbeinu Bahya

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Siftei Chakhamim

By which prayer is described, as is stated in Sifrei. The following [are the ten terms: 1.שועה. 2.צעקה. 3.נאקה (three types of crying out). 4.רנה (song). 5.פצור (press). 6.קריאה (call). 7.נפול (fall). 8.פלל (plead). 9.פגיעה (approach). 10.תחנה (supplicate).
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Or HaChaim on Deuteronomy

Moses' entreaty also demonstrated four conditions which are necessary in order for one's prayer to be accepted. 1) One needs to pray in a manner similar to a poor man who knocks on a door in order to obtain some alms or some food as a hand-out, as we have been taught in Proverbs 18,23: "the poor man speaks beseechingly." 2) The prayer must be addressed to the source of Mercy, i.e. G'd Himself in His capacity as the attribute of Mercy. 3) It must be offered at a time when prayers are accepted, as we know from Psalms 69,14: "May my prayer to you come at a favourable moment, etc." 4) The prayer must be specific, incapable of being interpreted wrongly. This point is illustrated by Esther Rabbah at the beginning of chapter 7 item 24. [The Midrash discusses the meaning of the words in Esther 3,14: "that the people should be ready for this date," without specifying what precisely they should expect to happen on that day. The point is made that predictions made by Gentile prophets are obscure, liable to be misunderstood, whereas predictions made by Jewish prophets are clear and unambiguous. Ed.] The example quoted concerns a Jewish traveller who tired of the long trek he had to walk and whose ankle gave out. He said: "I wish I had a donkey." Shortly thereafter a Roman whose ass had just given birth to a young donkey passed him and told him to take it and to carry it. The traveller acknowledged that his prayer had been heard but that he had not expressed his prayer appropriately. He had failed to specify for what purpose he had requested the donkey. Thus far the Midrash. The word ואתחנן is the appropriate terminology when one beseeches G'd. By using this word Moses had complied with the first of the four conditions needed for a successful prayer. When he added אל השם, he complied with the second condition, i.e. he addressed his prayer to the attribute of Mercy. When he said בעת ההיא, he indicated that he had waited for the appropriate moment to offer up his prayer, i.e. a moment when G'd was known to be in a favourable frame of mind. Who would know better when such a time occurred than Moses? Perhaps this had been at the moment when G'd had said החל רש, "begin to possess and inherit his land" (Deut. 2,31). This would be in line with the view of our sages who said that Moses offered this prayer after the Israelites had defeated Sichon and Og and conquered their lands. By having waited for the appropriate time Moses had complied with the third of the four conditions for successful prayer we have listed earlier. Moses complied with the fourth condition for successful prayer when he said לאמור, i.e. he was precise in the formulation of his prayer, making it impossible to misunderstand. I have pointed out repeatedly that the word לאמור is often used to indicate that whatever immediately precedes it does not necessarily describe the exact words being used. Some of our commentators such as the author of the Yalkut Shimoni hold that the words בעת ההיא, "at that time," refer to Numbers 20,12 when G'd had told Moses and Aaron: "you (both) will not bring this community to the land I have given to them." On the other hand, Midrash Rabbah claims that the time Moses offered this prayer was on the occasion of Numbers 27,18 when G'd had told Moses to appoint Joshua as his successor. It is possible that Moses prayed a similar prayer on each of the occasions mentioned.
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Siftei Chakhamim

After I had captured, etc. Rashi has the following difficulty: Above it is written (Devarim 3:21), “And Yehoshua I commanded at that time, etc.” which means at the time of capturing Sichon and Og. And, “I pleaded to Adonoy,” refers to that verse [therefore the phrase here, “at that time,” is apparently not necessary]. Rashi answers: After ... I imagined that the vow had been partially cancelled. Therefore, [at that time] I thought to pray in order to enter the land, etc. (Re”m).
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Siftei Chakhamim

I imagined that the vow had been cancelled. You might ask: Since the vow had been cancelled, why then did Moshe need to pray? The answer is that Moshe thought the following: Before the land of Sichon and Og were conquered, it did not occur to me to pray because the Almighty had made a decree along with a vow, and therefore prayer would not help. But after conquering the land, and Bnei Gad, Bnei Reuvein, and half the tribe of Menashe inherited it, I thought that perhaps the vow had been cancelled — for a vow which is partially cancelled becomes totally void. If so, then the Almighty’s decree is without a vow and thus prayer will help.
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Siftei Chakhamim

This is one of the three occasions, etc. Re”m writes that Rashi is difficult to understand. For Sifrei lists five places, and Rabbi Elazar ben Azaria mentions four occasions where Moshe said, etc., and they are all listed explicitly. If so, Rashi’s words do not match either opinion. But it seems to me [the answer is]: Rashi’s commentary, “This is one of the three occasions, etc.,” means that Moshe prayed for these things and requested for the Almighty to fulfill his request and to make known to him if his request will be fulfilled. Such as regarding Miriam (Bamidbar 12:13) where Moshe requested she should be healed from tzara’as. Also regarding (Ibid. 27:15), “Almighty, appoint etc.,” where Moshe requested that his sons inherit his position of leadership — as Rashi explains there. And also here, Moshe is praying to cross the Yardein. But the other two occasions quoted in Sifrei are different. “Moshe spoke before Adonoy saying, etc. (Shmos 6:12),” where Moshe requested to know if You would redeem them, etc. And also, when “Moshe cried out to Adonoy saying ‘What shall I do to this people,’, etc. (Ibid. 17:4),” where Moshe requested to know if he would fall into their hands, etc. These two occasions were only a request to be informed, but not a request and prayer for the Almighty to fulfill what he is asking for. This answer can be found here in Rashi’s words, if you read the text carefully.
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