While listening to This American Life recently, I came across the teachings of
Rabbi Maimonides. One of his more famous teachings (and the one mentioned in the episode I was listening to) is the Ladder of Tzedakah (Charity.) In it he enumerates the levels charity from least to most preferred with the intention of encouraging more (and better)
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Interesting reordering of the levels of charity; I'd agree that there is a fundamental issue in giving between the cheerful/grudging aspect of it.
The anonymity factor, from what I've found, is an idea that you don't want to embarass people, and for many it's embarassing to ask for charity, or give it. Whether that ranks as highly as the rabbinic sages place it I can't say.
I would point out that you seem to be missing Maimonides' top level of giving, of giving someone a loan, training, or business partnership -- giving them the self-sufficiency to not need ask someone for charity again.
Interesting thoughts to ponder at 2am when I should be working on my coursework...
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