First time visitors to Israel are often surprised by the number of beggars walking the streets. Tourists approaching holy sites are often relentlessly bombarded by seekers of donations and hand-outs.

When approached by beggars in Israel, I respond the same way I do when approached by the homeless in San Diego: I almost always refuse to give them money. I prefer to help the homeless and indigent by contributing to organizations I know will responsibly manage and distribute funds donated to help the needy.

There are times, however, when I decline with great reluctance. The Torah says: "If your kinsman becomes poor you shall strengthen him . . . " (Lev. 25:35) What if the person who is asking for money truly needs the funds to purchase his or her next meal, rather than to buy cigarettes or alcohol? Am I ignoring the mitzvah to help need by turning aside? Would it not be better to err on the side of helping someone running a scam, rather than to decline aiding those truly in need?

This question does not have a simple answer. Yet, experience has taught me that more good is done by contributing to organizations geared toward helping the poor, than by giving money to individuals.

Not everyone feels this way.

Rabbi David Segel was well known for his exceptional generosity. The poor would come from far and wide to receive his gifts and tzedakah.

One day a stranger appeared at Rabbi David’s door and asked him to lend him a shekel. Rabbi David reached into his pockets and realized that he did not have even a penny to give the man. Rabbi David immediately went into his house and came out with the silver Kiddush cup he used every Friday night to welcome Shabbat. He told the traveler to take the Kiddush cup to the town’s pawnbroker and exchange it for the shekel he needed. On Friday Rabbi David would receive his salary from the community and redeem his cup in time for Shabbat.

The stranger took the silver cup to the pawnbroker and asked for, and received, a loan of two shekels in exchange for the cup.

On Friday, Rabbi David sent a messenger to redeem his cup. When the messenger presented the single shekel the rabbi gave him, the pawnbroker said: "That’s not enough. I lent out two shekels for the cup and that is the amount I need in order to return it."

The messenger hurried back to Rabbi David, who beamed with joy, and reached into his pocket for the additional shekel.

The messenger was perplexed and asked Rabbi David to explain his great pleasure at having to pay more money. Didn’t he know that the stranger had taken advantage of him?

"You don’t understand," replied Rabbi David. "When the stranger came to me he must have really needed two skekels, and not one, but was too embarrassed to ask me for them. It was a good thing that I did not have any money, because if I had the shekel he had asked for I would have given it to him and it would not have been enough! He still would have needed an additional shekel. This way I was able to give him everything he needed! That is why I am so happy!" (Shivim Panim L’Torah, Vayikra, p. 230)

Most of us would not have had the same response, either to the request or after finding out we had been misled. We would have felt taken advantage of, whereas Rabbi David felt blessed.

Which leaves us with two thought-provoking questions: 1) How do we know the right thing to do when approached by an alms-seeker, and 2) was Rabbi David a tzaddik or a fool