Levels of Charitable Giving
8. When donations are given grudgingly.
7. When one gives less than he should, but does so cheerfully.
6. When one gives directly to the poor upon being asked.
5. When one gives directly to the poor without being asked.
4. Donations when the recipient is aware of the donor's identity, but the donor still doesn't know the specific identity of the recipient.
3. Donations when the donor is aware to whom the charity is being given, but the recipient is unaware of the source.
2. Giving assistance in such a way that the giver and recipient are unknown to each other. Communal funds, administered by responsible people are also in this category.
1. The highest form of charity is to help sustain a person before they become impoverished by offering a substantial gift in a dignified manner, or by extending a suitable loan, or by helping them find employment or establish themselves in business so as to make it unnecessary for them to become dependent on others.
(based on Yad, Matanot Ani'im X 114)
Source: Shamash and Donin, Hayim. To Be a Jew: A Guide to Jewish Observance in Contemporary Life. NY: Basic Books, 1991.