King David writes that “Fortunate is the one who understands the needy” (Psalm 41:2)
It is easy to write a check, but helping others with sensitivity is an art. The Satmar Rebbe was a true artist when giving tzedaka. Someone from Israel once came to see him at his synagogue in Brooklyn with a pressing need. His wife needed surgery and he came to the Rebbe asking for ten thousand dollars. The Rebbe told his assistant to write the man a check for $9,700.00. The man was thrilled and thanked the Rebbe profusely.
Afterward, the assistant asked the Rebbe that if he gave that much, why he didn’t just give the man the ten thousand dollars he requested. The Rebbe wisely said that if he gave the man everything he asked for, he would probably leave kicking himself for not requesting more. So giving him a little bit less allowed him to leave totally appreciative and with no regrets.
The laws of Tzedaka (charity) place a tremendous emphasis on giving in a way that maintains the dignity of the recipient. In fact, in Maimonides’ eight levels of charity, the highest is to give someone a loan or a job to help get them on their feet so they’ll no longer need to receive charity
There were two friends who were full-time Talmud scholars. One was very poor but very proud and was very reluctant to receive help from others. One day, his friend called him and said that there was a huge sale on tuna fish at the grocery store. The cans were slightly damaged, so they were marked down 75%. “Would you like me to pick you up a dozen cans? You can pay me when I bring them to you.” His friend was thrilled and very appreciative.
Of course, the cans of tuna were not really damaged or on sale. The friend purchased a dozen cans, went home and took out his hammer to give each one a small dent. His friend was thrilled to pay for this bargain and didn’t feel that he was getting a special handout.