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DEUTERONOMY — 15:10 evil

DEUT782 He who gives charity to the poor with a mean expression loses his merit, and he transgresses (this verse): "And let your heart not be evil when you give to him," even if he gives much. It is better to give a perutah [a small coin] with a pleasant expression. The ideal is to give correctly to a deserving poor man, with a pleasant expression. It is better to give before one is asked, and to give in secret, as it is written (Mishlei 21:14): "He who gives in secret suppresses wrath." Some men were in the practice of tying money in a piece of cloth and casting it behind them for the poor (Kesubos 67b), so that the giver did not know to whom he had given and the recipient from whom he had taken, thus sparing the poor embarrassment. In summary: Whatever can be done in secret, so that the poor man does not know the giver and the giver does not know the recipient, should be done. And when a man gives charity, he should accompany it with lovingkindness, such as buying with his money something that the poor man needs in order to spare him the bother of buying it himself. Or, finding that a poor man's needs can be cheaply acquired at a certain time, but that he is lacking in means, you should supply him with the necessary funds, making sure to do so at that particular time, thus showing lovingkindness. About this the prophet has said (Hoshea 10:12): "Sow for yourselves with charity; harvest with lovingkindness." That is, the reward is commensurate with the lovingkindness (Sukkah 49b).

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DEUTERONOMY — 15:10 give

DEUT786 We read in Scripture … "Give shall you give to him, and your heart shall not be grieved…" [this verse]. Rashi quotes the Midrash (Sifre) about the double verb: "Give shall you give--even a hundred times." People often use the expression, "Give till it hurts"; Scripture indicates that the more you give, the less it hurts! "Give … give" without stinting or counting, "and your heart will not be grieved." The more often you donate, the greater your sense of good accomplished, and the better you feel. Become a "veteran giver," and you will feel no pain, only a Divine gladness. Alas for the wicked man: he will not take even the first step.

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DEUTERONOMY — 15:10 readily

DEUT789 No limitation has been set for the number (even if it reaches 100) of times the loans are to be granted. The person approached should not resent the inconvenience and be annoyed by the borrower pestering him so many times, coming to borrow or to repay, just as one never resents the constant visits to one's store of a regular customer from whom one profits. The lender should remember that each time he lands, he is fulfilling a positive commandment of the Torah. God's blessing will rest on him, since Scripture has given its assurance in a similar case of charity [this verse]: "Give--give to him (the repetition implying over and over again, even 100 times [Rashi], and your heart shall not be grieved; because for this thing, Hashem, your God, will bless you in all your work..."

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DEUTERONOMY — 15:10 regrets

DEUT790 "You shall continually give him, and you must not feel bad when giving him" [this verse]. We have herein been admonished to distance ourselves from meanness of spirit [Lit., "narrow-eyed." It refers to one who resents the success of others, and does not help them willingly.] But to be magnanimous, similar to what the pasuk says (Mishlei 22:9), "A magnanimous person is blessed." Is not enough to [merely] open our hand and give; rather, we must implant within our souls the trait of generosity. Therefore, the Torah admonishes us by saying, "You must not feel bad [when giving him]," subsequent to its saying, "You shall continually give him."

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