(1) We must be especially careful to observe the mitzvah of tzedakah, more so than any other positive mitzvah, for tzedakah is a sign of the righteous [tzadik] lineage of Abraham, our father...
(2) Never has anyone become poor by giving to tzedakah, nor has anything bad ever come of it, nor has any harm occurred because of tzedakah, as it is said, (Isaiah 32:17) The work of righteousness [tzedakah] is peace. Anyone who shows compassion, others will show compassion to him... And if someone is cruel and without compassion, then his lineage is suspect, for cruelty is only found among the idolatrous nations...And if a brother does not show compassion for another brother, then who will have compassion for him? And to whom can the poor of Israel look? To the idolatrous nations that hate them and pursue them? They can only look to rely upon their brothers.
(3) Anyone who averts his eyes from [the need of] tzedakah is called Belial ["Wickedness"], just as the idolaters worship Belial, and of the idolaters Scripture says, (Deut. 13:14) That some scoundrels [children of Belial] from among you have gone [and subverted the inhabitants of their town] by averting their eyes from [the need of] tzedakah. It says, (Deut. 15:9) Beware lest you harbor a base [belial] thought.180 Such a person is called, "a sinner," as it is said, (Deut. 15:9) He will cry out to the LORD against you, and you will incur a sin.Therefore, one needs to be especially sensitive to their cries, for they [the poor] have a covenant established [between them and God], as it is said, (Exodus 22:26) Therefore, if he cries out to Me, I will pay heed, for I am compassionate.
(4) Anyone who gives tzedakah to a poor person with a scowl and causes him to be embarrassed, even if he gave him a thousand zuz, has destroyed and lost any merit thereby. Rather, one should give cheerfully, with happiness [to do so] and empathy for his plight, as it is said, (Job 30:25) Did I not weep for the unfortunate? Did I not grieve for the needy? And one should speak to him words of comfort and consolation, as it is said, (Job 29:13) [I received the blessing of the lost,] I gladdened the heart of the widow.
(5) If a poor person asks of you [to give him something], and you do not have anything in your possession to give to him, comfort him with words. It is forbidden to speak harshly to a poor person or to raise your voice in a shout, for his heart is broken and crushed. Thus it says in Scripture, (Psalms 51:19) God, You will not despise a contrite and crushed heart. And it says, (Isaiah 57:15) Reviving the spirits of the lowly, reviving the hearts of the contrite. And woe to anyone who shames a poor person! Woe to him! Rather, let him be like a father to him, in compassion and in words, as it is said, (Job 29:15) I was a father to the needy.
(6) One who coerces others to give tzedakah is considered to have performed even a greater deed then the person who actually gives...
(7) There are eight levels of tzedakah, each one greater than the other. The greatest level, higher than all the rest, is to fortify a fellow Jew and give him a gift, a loan, form with him a partnership, or find work for him, until he is strong enough so that he does not need to ask others [for sustenance]. Of this it is said, (Lev. 25:35) [If your kinsman, being in straits, comes under your authority,] and you hold him as though a resident alien, let him live by your side. That is as if to say, "Hold him up," so that he will not fall and be in need.(8) One level lower than this is one who gives tzedakah to the poor and does not know to whom he gives, and the poor person does not know from whom he receives. This is purely a mitzvah for its own sake, such as the Chamber of Secrets in the Holy Temple, for there the righteous would give in secret [and leave], and the poor, of good background, would sustain themselves from it in secret. Very close to this is one who gives to the kupah of tzedakah, but one should not contribute to the kupah of tzedakah unless one is certain that the one who counts it is trustworthy and wise and behaves competently, as was Rabbi Chanania ben Teradion.
(9) One level lower is one who gives tzedakah and the giver knows to whom he gives but the poor person does not know from whom he takes. Such did the great sages who would go in secret and throw money onto the doorways of the poor. A method such as this one is a good way when the keepers of tzedakah do not behave competently.
(10) One level lower is when the poor person knows from whom he takes but the giver does not know to whom he gives. Such was the way of the sages who would tie coins to their garments and would throw the bundle over their shoulder so the poor could come up [behind them] and take [them] without being embarrassed.
(11) One level lower is to give to him with one's own hand before he can ask.
(12) One level lower is to give to him after he has asked.
(13) One level lower is to give him less than one should but with kindness.
(14) One level lower is to give to him begrudgingly.