If one has $100 to give to charity, is it better to give it all to one person, or distribute $1 to 100 people (so that if one isn't legit, the others will cover)?
Answer
From here (based on Maimonides Commentary on the Mishnah, Avot 3:15) :
The Chofetz Chaim, Rabbi Yisrael Meyer HaCohen Kagan, says that this explains how we should give Tzedakah, charity. He says it is better for an individual if he or she gives 100 individual dollars to 100 poor people, than all to one person. This way, one becomes accustomed to fight against his miserly inclinations 100 times, and it becomes easier to win in the future. Furthermore, giving Tzedakah becomes a completely natural act, given that one has become accustomed to giving by doing so such a large number of times.
I just found this story about a Chassid who, when asked for charity, would always give it in two parts, so that he could fight his inclination twice for every time he gave charity.
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