Some Clarity in Charity
Rather, you shall open your hand to him; you shall lend him his requirement, whatever is lacking to him. (Deut. 15:8)
The Torah tells that we should give a person "whatever he is lacking to him." The Sages learn from the words "to him" that we must give charity according to each individual's needs. If a person was wealthy and lived an extravagant lifestyle and then became poor, we must give him to the extent that he can live in accordance with his previous standing. If he used to drive a fancy car, we must get him that car. The question arises: if I myself would never pay so much, why must I pay for him?
An important factor in the act of giving charity is to ensure the emotional well-being of the beneficiary. When a person loses his assets the emotional strain may be greater than the physical one. When a wealthy person loses his fancy car the embarrassment is unbearable. It is equivalent to a pauper who is evicted from his apartment, even though the wealthy person can still live a normal life. Therefore, providing the wealthy person with his fancy car is literally giving him his life back just as much as paying the rent for a pauper.
It is for this reason that one who provides a poor person with money and adds kind words of encouragement receives twice as many blessings from God for adding the kind words as he does for simply giving the money!(1)
It takes a special person to be able to recognize the emotional needs of another, especially one from a different background. The Talmud (2) relates that Hillel, who was perhaps the poorest Torah scholar, raised money for a wealthy man who lost his money to purchase a horse to ride upon and a slave to run before him. On one occasion he could not find a slave to run before him, so Hillel took his place and ran for three miles! Despite Hillel's poverty, he was able to understand the needs of a wealthy man - to the extent of personally providing those needs!
1. Tosafos Baba Basra 9b.
2. Kesubos 67b.