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נָת֤וֹן תִּתֵּן֙ ל֔וֹ וְלֹא־יֵרַ֥ע לְבָבְךָ֖ בְּתִתְּךָ֣ ל֑וֹ כִּ֞י בִּגְלַ֣ל ׀ הַדָּבָ֣ר הַזֶּ֗ה יְבָרֶכְךָ֙ יְהוָ֣ה אֱלֹהֶ֔יךָ בְּכָֽל־מַעֲשֶׂ֔ךָ וּבְכֹ֖ל מִשְׁלַ֥ח יָדֶֽךָ׃
Ты непременно отдашь его, и сердце твое не опечалится, когда ты отдашь ему; потому что за это Господь Бог твой благословит тебя во всех делах твоих и во всем, что ты положишь руку твою.
Rashi on Deuteronomy
נתן תתן לו THOU SHALT SURELY GIVE HIM — even hundred times (Sifrei Devarim 117:6).
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Kli Yakar on Deuteronomy
For because (biglal) of this thing, the Lord will bless you: The Rabbis, may their memory be blessed (Shabbat 151b), learned from the expression, biglal, that it is a cycle (galgal) that repeats itself in the world. But many wondered about the expression, since biglal is not [related to] galgal, as behold, a [letter], gimmel is lacking [in the former]. And I say that their intention, may their memory be blessed, was to understand biglal as related to the usage, "and they would roll (gallelu) the stone" (Genesis 29:3). And [by this], they wanted to say [that] when poverty goes around among people from this one to that one - as is customary - then "the Lord will bless you," and cause that it not roll over and fall upon (crush) you when it falls on people. And axiomatically, we learn that the thing goes around in the world like a cycle, such that everyone who gives will in the end [also] receive. As that is the trait of everything that exists in all three of the worlds, that everything that gives will come back to [also] take, in the way that we explained above in Parshat Bereshit on the verse, "the sixth day" (Kli Yakar on Genesis 1:31:5). As with everything that exists, the thing moves like a cycle, that each one of them gives and receives, except for God alone - He gives and does not receive.
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Rabbeinu Bahya
נתון תתן לו, “You shall surely give him, etc.” The reason the Torah repeats the word נתן is to tell you that if you will give the poor in adequate measure, the Lord in turn will give you in adequate measure. Our sages interpreted the words to mean that even if you are called upon 100 times to support the same individual, do not refuse. The latter demand is based on your not having given the poor enough support the first time.
Concerning this subject Solomon said in Proverbs 21,26: “while the righteous man gives without stint.” Solomon means that the righteous does not allow any considerations to deflect him from giving charity. Another nuance included in the wording of the Torah נתון תתן is that one should give charity in a pleasant manner, not grudgingly. Neither should one do so in an arrogant manner. By following all these implications contained in the Torah’s wording, one may merit that one’s own wealth will endure. Concerning this Solomon said in Proverbs 13,8: “the poor never heard a reproof.” When does a man retain his own wealth? When he does not make the poor believe that his misfortune may be of his own doing, and one gives charity with a pleasant countenance. This is reflected in the story told by our sages about Rabbi Yannai who said to a wealthy man who publicly gave an alms to a poor man: “it would have been better if you had not given to this man at all instead of publicly embarrassing him” (Chagigah 5).
Concerning this subject Solomon said in Proverbs 21,26: “while the righteous man gives without stint.” Solomon means that the righteous does not allow any considerations to deflect him from giving charity. Another nuance included in the wording of the Torah נתון תתן is that one should give charity in a pleasant manner, not grudgingly. Neither should one do so in an arrogant manner. By following all these implications contained in the Torah’s wording, one may merit that one’s own wealth will endure. Concerning this Solomon said in Proverbs 13,8: “the poor never heard a reproof.” When does a man retain his own wealth? When he does not make the poor believe that his misfortune may be of his own doing, and one gives charity with a pleasant countenance. This is reflected in the story told by our sages about Rabbi Yannai who said to a wealthy man who publicly gave an alms to a poor man: “it would have been better if you had not given to this man at all instead of publicly embarrassing him” (Chagigah 5).
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