For an explanation of the methodology of this series, see the introduction.

"I entreated G‑d at that time, saying:" (Deut 3:23)

Peshat (basic meaning):

Rashi: "I entreated/Vaet’chanan"
...the righteous ...request only a free gift of the Omnipresent. The root of the word chanun [and its derivatives] in all cases is an expression signifying or requesting a free gift. Even though the righteous may base a request on the merit of their good deeds, they request only a free gift of the Omnipresent. Because God had said to him [Moses], "v’chananti/and I will favor whom I wish to favor," (Exod. 33:19) he [Moses] spoke to Him [G‑d], using the expression Vaet’chanan.

Siftei Chachamim: Rashi explains why the verse did not use "I prayed" instead of "I entreated".

"at that time"
After I had conquered the land of Sichon and Og, I thought that perhaps the vow [which God had made, that I should not enter the land] was nullified [since the land I entered was to become part of the land of Canaan].

This is one of three occasions in which Moses said before the Omnipresent, "I will not let You go until You let me know whether or not You will grant my request. "

Remez (hinted meaning):

Baal HaTurim: "I entreated"
Written in the verse just before this, Moses tells Israel, "Do not fear them." Moses thought "if I encourage Israel, perhaps G‑d will have mercy on me."

"I entreated"
The gematria of this word is that of Shira/song. Moses recited songs of phrase before G‑d so that He would accept his prayer.

Derash (interpretive meaning):

Ramban: "at that time"
refers to the time "when I conquered Sichon and Og and I began to war against the nations given to Israel and I allocated the land to the 2 tribes, Reuben and Gad." Moses prayed then for mercy and pleaded to be allowed to enter the Land of Israel. When G‑d did not hearken to him, Moses then prayed for the appointment of a successor. Scripture mentions then his latter prayer which was affirmatively answered. Here Moses mentions 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.

...although the Land was beloved to him, he did not merit to enter it because of them.

Ohr HaHayyim: Moses' entreaty demonstrated 4 conditions necessary for one's prayer to be accepted:
(1) one must pray similar to a poor man who knocks on a door for a hand out, as "the poor man speaks beseechingly." (Prov. 18:23)
(2) the prayer must be addressed to the source of Mercy [to G‑d in His capacity of Mercy].
(3) it must be offered at a favorable time, "May my prayer come to you at a time of goodwill.'
(4) the prayer must be specific and incapable of improper interpretation.

Moses used the term 'vaet'chanan' to fulfill the 1st condition. When he added "to Havayah" [the four-letter Name], he complied with the second condition. When he said 'at that time', he indicated that he waited for right moment. Moses complied with the 4th condition by adding 'saying'; meaning he was precise in formulating his prayer, making it impossible to misunderstand.

Tzeror HaMor: Seeing that G‑d had delivered Sichon and Og into the Israelite's hands, Moses now relates that he had made an appeal to G‑d on his own behalf, confirming what our Sages said in Berachot 10 that even when the hangman's noose is on the head of the condemned man, the victim should not despair that G‑d may show him mercy. Although Moses knew he was not allowed to set foot on the west bank of Jordan River, he still pleaded with G‑d to rescind the decree 'at that time' — even at that late point in time.

Imrei Shaul:
"At that time"
It means we should be looking in all of our prayers towards "that time" of great transformation, with confidence "that time" will come.

Tzemach David:
"At that time"
It means we must accept the level of awareness we presently occupy without jumping out of ourselves toward an ambitious level, higher than the one where we really are.

Lekutei Divrei David:
"At that time"
It means that we should not pray with fear and worry about the needs that might be coming next in our lives, but be aware of the moment in which we are praying and pray for that moment's needs, with confidence that the subsequent moments will take care of themselves. aware of the moment in which we are praying and pray for that moment's needs...

Rav Yavay:
"At that time"
Even in a time of sorrow and difficulty one should ask G‑d for clarity to be able to pray.

Kedushat Levi:
means that Moses was praying about what he would next be saying...he was praying that he would be able to speak and say and pray with clear intent.

Sod (esoteric, mystical meaning):

Zohar Vaet'chanan 260:
"And I besought G‑d at that time, saying, G‑d Elokim, You began to show Your servant." (Deut. 3:23-24) Rabbi Yosi opened with, "Then Hezekiah turned his face toward the wall, and prayed to G‑d." (Isaiah 38:2) Come and see, how powerful is the force of the Torah and how superior it is to anything else. For whoever is occupied with the Torah does not fear the higher or lower beings, nor fear evil incidents in the work, because he is connected to the Tree of Life, and daily eats from it.

For the Torah teaches man to walk the path of truth and gives him counsel how to repent before his Master. Even when he is sentenced to death, everything is repealed and gone from him, not to rest upon him. Therefore he should be occupied with the Torah day and night and not move from it. This is the meaning of, "but you shall meditate therein day and night." (Joshua 1:8) If he removed the Torah from himself or separates from it, it is as if he separated from life.

Come and see, there is advice for man. When he climbs into his bed at night, he should accept upon himself the yoke of the kingdom of heaven wholeheartedly and hasten to give Him the deposit of his Nefesh. It was explained that this is because every man tastes the taste of death, because the tree of death rests upon the world. And all the spirits of people come out, rise and hide in it. Since they are as a deposit, they all return to their place.

He comes to the synagogue, cleanses himself by reciting the offerings, and sings the praises of King David. Fastened with Tefilin on his head and Tzitzit at the corners of his garment, he recites "A praise of David." (Psalms 145) It was explained that he who prays before his Master should stand when praying like the supernal angels and join those who are called 'those who stand, as written, "I will give you access among these who stand," (Zachariah 3:7) to concentrate his will before his Master and submit his petition.

Come and see, when man rises at midnight from his bed to be occupied with the Torah, a crier announces over him, saying, "Behold, bless G‑d, all you servants of G‑d, who stand by night in the house of G‑d." (Psalms 134:1) Now when he stands in prayer before his Master, the crier proclaims about him saying, "I will give you access among these who stand." behooves him to deliver his soul with a willing heart to the required place.
After finishing his prayer favorably before his Master, it was explained that it behooves him to deliver his soul with a willing heart to the required place. Man has many counsels about anything. When he is in prayer, all the words man utters in his mouth in that prayer rise up and cleave airs and firmaments until they reach wherever they reach. They are adorned on the head of the King, who turns them into a crown. The colleagues explained that when a man asks G‑d in his prayer, he should meditate for it to be a prayer of supplication. Whence do we know that? From Moses, as written, "And I besought G‑d." (Deut. 3:23) Such is a goodly prayer.

BeRahamim LeHayyim:
One cannot just rely on the simple or the basic explanation of the Torah. Sometimes it covers over deeper levels. Here Rashi explains why the Torah did not use the more common word "I prayed" and instead used "and I entreated".

But the Holy Zohar speaks only about man's daily prayer, his tefila, perhaps because tefila is the same gematria as vaet’chanan! Ramchal wrote a book of 515 prayers, and the above Zohar describes the prayer ritual from sleep, through Tikkun Hatzot/Midnight Prayer, and including the morning Tachanun, explaining the elevation of prayer.

Prayer cannot be empty words. It must come from the deep chambers of the heart, a true supplication. If so, the prayer, with the help of the angel Sandal-phon, will be turned into a crown on the head of the king. Prayer comes out from the mouth, and in Petach Eliyahu, we learn that the emanation malchut corresponds to the mouth. Malchut has its own relationship to Keter, the "highest" of the emanations: Keter Malchut. A King is a man with a crown, meaning a surrounding light not in his head but around it, a light of nobility, a light bestowed from above. The Divine right of Kings.

When we pray well, we give strength to G‑d. And we also make Him our king, over and over again.

When we stand by G‑d in prayer, we gain access. The doors of the palace are opened for those who come to call, to those who come to call in truth.

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