What is the connection between "Nason Titen lo ve'Lo Yeira Levacha ... "?
It means simply that a. one should give Tzedakah, and b. when giving, one should not give begrudgingly. 1
Oznayim la'Torah: If one gives again and again, giving becomes second nature and one will never feel bad about having to give.
Why does the Torah repeat the words "Nason Titen lo"?
Kol Eliyahu: "Nason Titen lo" and "be'Sitcha lo" hint at four levels of giving Tzedakah. 1. You do not know to whom you are giving, and the recipient does not know who gave - "Nason"; 2. You do not know to whom you are giving, but the recipient knows who gave - "Titen"; 3. You know to whom you are giving, but the recipient does not know who gave - "lo"; 4. You know to whom you are giving, and the recipient knows who gave - "be'Sitcha lo". 2
Sifri: To teach us that even one already gave the poor man once, should the need arise, one should give him again - even a hundred times.
Bava Metzi'a, 31b: To teach us that, even if one is not able to give a large donation, one should give a small one (according to one's means). 3
These are first, third, second and fourth best (CM 249:7-10). Kol Eliyahu explained the order of how we extrapolate them. In fact, helping him to support himself is preferable to all of these. Moreover, there are three other levels below those listed ? giving only after the poor man asks, giving less than is appropriate, and giving reluctatly (CM 249:6, 11-13).
See Torah Temimah, note 34.
What are the implications of the word "Nason Titein Lo"?
Rashi (citing the Sifri): It implies that one should give the poor man discreetly - between himself and the poor man (And the Chachamim learnt from here to build a special chamber in the Beis Hamikdash, 1 where those who feared sin could deposit money which was used to sustain the poor of good stock in a discreet manner.
Refer to 15:10:1:2.
Called the Lishkas Chasha'im (Sifri).
Why does the Torah use the unusual expression "Ki Biglal ha'Davar ha'Zeh"?
Shabbos, 151b: Poverty is a wheel (Galgal) that goes round the world from which nobody is immune. 1 If it does not strike him, it will strike his son; and if not his son, his grandson ? and that one therefore needs to Daven that it should not strike him.
Moshav Zekenim (in Vayikra 25:17): We read "Biglal" like 'be'Galgal' (the celestial sphere). 2 ? If the Ashir does not give to the Ani, Hashem switches [their Mazalos on the] Galgal (and the Ashir will become poor, and the Ani rich). 3
Oznayim la'Torah: Just as the wheels of a wagon cause it to move, and not only removing them - to lighten the load will fail to enable it to go faster, it will stop it from moving altogether - Tzedakah is the wheels of Parnasah, and not only will stopping giving Tzedakah not incease one's wealth, it will completely cut off one's source of Parnasah. 4
See Torah Temimah, note 37.
By means of the celestial sphere.
In keeping with the Pasuk in Mishlei 22:2 "Ashir va'Rash Nifgashu Oseh Chulam Hashem".
See Oznayim la'Torah, who elaborates, concluding wiqth the Gemara in Gitin, 7 - 'If someone sees that his Parnasah is tight, let him give Tzedakah - and he will see no more signs of poverty'.
What are the implications of the words " ? ki bi?Gelal ha'Davar ha'Zeh"?
Rashi: It implies that, if one declares that he will give Tzedakah, he will receive reward for his words as well as for the actual giving. 1
Kol Eliyahu: "Biglal ha'Davar ha'Zeh Yevarech'cha" - for giving Tzedakah to an Ani one receives six B'rachos, and for appeasing him with kind words (Devarim), another eleven, seventeen 2 in all.
Torah Temimah (citing the Tosefta in Pe'ah, Perek 4): He will receive reward for his words even if, for some reason, he does not manage to give, if he asks others to give or if he just speaks words of encouragement to the Ani. See note 38
Kol Eliyahu: Equal to the Gematriya of te word "bi'Gelal ha'Davar ha'Zeh".
What form will the ensuing B'rachah take?