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When it comes to charity, what are the guidelines for the most effective way of giving?
I once heard a concept that a person should study the Torah laws even as they relate to performing acts of kindness, because there is always a better, more effective way of doing kindness, according to our Jewish tradition. When it comes to giving charity, can you provide some guidelines?
You are correct about there being better ways to do this. The Code of Jewish Law (following Maimonides' Laws of Gifts to the Poor 10:7-14) describes eight different levels of charity:
1) The highest category is someone who strengthens a fellow Jew in need by a gift, loan, or offer of partnership or employment.
From here comes the Jewish concept of a free loan fund, called a Gemach. If you help someone start a business, he can feed himself and 10 other people besides. As the old saying goes: Rather than give him fish to eat, teach him to be a fisherman.
Actually there's even one higher level of tzedakah: being sensitive to someone before he's in trouble. As the Sages explain: It takes one person to support something before it falls, but after it falls, even five people may not be able to lift it. (see Rashi, Leviticus 25:35)
What if you offer someone a job and he's too lazy to work? Then you don't have to give him anything. The Talmud says: If he doesn't care about himself, then you're not required to care about him, either.
2) The second-highest category is when the donor does not know the identity of the recipient, nor does the recipient know the identity of the donor. This saves the recipient embarrassment. It also means that the giving is more altruistic, since there is no possibility of being honored for the donation. Many people fulfill this by contributing to a charity fund.
3) The next lower category is a donor who knows the recipient, though the recipient does not know the donor. For example, great Sages used to secretly deposit money at the doorsteps of poor people.
4) The next category is when the recipient knows who the donor is, but the donor does not know who the recipient is. For example, some Sages used to wrap money in a small package and toss it behind them. The poor who came to collect the money were spared any shame.
5) The next category is one who gives to a poor person before he asks.
6) The next lower category is one who gives to a poor person after he asks.
7) The next category is one who gives an amount less than appropriate, but in a pleasant and cheerful manner.
8) The lowest category is one who gives ungraciously.