Maimonides' Ladder of Tzedakah
The best forms of charity make the recipient self-sufficient.
Where the recipient is aware of the source of the charity but the giver does not know to whom the money is being given, the degree is lower [since the recipient, knowing who gave him the money, feels beholden to him and ashamed in his presence]. Yet, there is merit since the poor are saved from direct shame.
Of less merit is charity where both are known to each but [at least] the gift is made before the poor asks for it. [In this case the giver is showing care since he anticipates the needs of poor. The Patriarch Abraham does not wait for the stranger to come to ask for his assistance, but runs toward him and begs him to share his hospitality; this is the archetype of Jewish righteousness.]
[Clearly] where one gives charity after being asked for it is of a lower degree. [Since the method of giving charity is an integral part of charity], one who gives less than what is fitting but with good grace [is of higher merit than] one who gives unwillingly.
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