Q. Is there a chiyuv to give at least some tzedakah to every Jewish ani (poor) who asks? If yes, what about someone who appears very suspicious, for example, you sometimes have someone who says his car broke down and he needs money for a bus, and it appears he is a fraud, but there is no way to know for sure. Assuming he says he is a Jew, is there a chiyuv to give him tzedakah?
A. On question 715 regarding if it was a mitzva the tzedaka given to a collector who turned out to be a fraud and a con, we wrote: “Poskim disagree whether giving tzedaka to a wicked or immoral individual is considered a mitzvah or not. Yad Remah (Bava Basra 9b,) deduces from the incident of Prophet Yirmiyahu (18: 23, Bava Kama 16b)) praying that the people of Anassoth even when they are prepared to do charity, Hashem should cause them to stumble and donate to the unworthy, that no reward is forthcoming for that charity.
Sefer Chasidim (61) adds that not only a mitzvah was not done, but also it would be considered an actual offense, since he is supporting undeserving and sinful individuals.
However, Gilyoney Hashas (Bava Kama 16b) deduces from Rabbenu Yonah’s permission to feed individuals who did not wash Netilas Yodaim, that one does comply with the mitzvah. Similarly, Nimukey Yosef (ibid.) maintains that if the givers intentions were to correctly observe the mitzvah, and he was unaware of the unworthy condition of the recipient, he complies with the mitzva.
The Chidah (Rosh Dovid, Shoftim) maintains that the above depends on the disagreement between Rabbi Meir and Rabbi Yehudah (Kidushin 36a) whether if Bnai Yisroel in a state of no compliance with the mitzvos are still called Bonim or Hasem’s Children.
Meromei Sade (ibid.) distinguishes between wicked or immoral people and individuals who fraudulently represent themselves as poor when they are not. Since you are not actually giving tzedaka to a poor man.
Horav Shlomo Miller’s Shlit”a opinion is that the giver complies with the mitzva in the sense of someone who wanted to do a mitzva and then he accidentally was not able to fulfill his wish (Kidushin 40a)”
See also question 716 regarding compliance in such cases, with maaser money obligation.
I was present when Horav Moshe Feinstein zt”l gave a small coin to a “pauper,” that although was known to be secretly well off, went around collecting in the shuls of the East Side. Horav Moshe explained that this individual collects just for the sake of being in contact with others and it is the acknowledgment of his presence by other people, what he really desires. Therefore, giving him a small coin meets his human needs and is a mitzva.
Horav Shlomo Miller’s Shlit’a opinion in the present shaila case is similar, if it conforms with the above description.
Rabbi A. Bartfeld as revised by Horav Shlomo Miller Shlit’a