I support needy families around the — area, and started doing that when I was in yeshiva in — and continue to fund those families there. No-one know I do this, and the families know what i do, but don’t know it is me. It is costing me roughly with, clothing, food, and yeshiva bills for them, 25,000 a month. Thank G-d I make about 35,000 a month. I can’t leave these people. I was wondering, do I actually have a halachic duty to stop? thank you
One is not permitted to give away more than one fifth of one’s possessions to tzedakkah. This is because there is a concern that one may oneself become poor and would then need to take charity from others. Therefore, a very wealthy man may give more than a fifth to charity if it is extremely unlikely that he will become impoverished.
Further, some poskim permit giving away more than a fifth if there is a poor person standing in front of you. In other words, it is only forbidden to give away more than a fifth if the money is being set aside for charity and is not being given away immediately, but in a case where a particular poor person requests money at this moment one may give away more. Your case, in which you are dealing with particular families that are relying on you, can be considered as just such a circumstance.
Also, in order to support needy Talmidei Chachomim, one may give away more than a fifth – this is considered an investment as any other (if not a better investment!).
[There are several other circumstances in which one may give away more than a fifth of one’s possessions to charity, such as on one’s deathbed. Furthermore, the Chafetz Chaim suggests that one who wastes his assets on unnecessary luxuries may well be permitted to give more than a fifth to charity, since the money would otherwise go to waste anyway!]
There are some Poskim who permit giving away more than a fifth of one’s earnings to tzedakkah (indeed the Shulchan Aruch (Y.D. 149:1) seems to permit it if one can afford it, with the Remo”h forbidding it, so perhaps there is more room for Sephardim, who follow the rulings of the Shulchan Aruch, to be lenient). Apparently, when Rav Yosef Sholom Elyashiv was asked he replied that he permits it. When he is summoned to the Heavenly Court, he added, he will present his Halachic reasoning for this ruling. If it is accepted, well and good, and if not – he is willing to accept upon himself the consequences!