A philosopher approached Rabban Gamliel with what he considered an unanswerable objection to the practice of charity. "How can you Jews give so freely to the poor?" the philosopher asked. "You cannot know whether your gift will be used wisely. The recipient may be lazy, or dishonest, or undeserving. Why not keep your wealth and invest it where you can guarantee a return?"
Rabban Gamliel smiled. The philosopher was thinking like a merchant — calculating risk, evaluating returns, demanding guarantees. But charity, the sage explained, operates on an entirely different economy.
"When I give to the poor," Rabban Gamliel said, "I do not give because I have evaluated the recipient and found them worthy. I give because God is the guarantor of the transaction. God Himself stands behind every act of charity, and God ensures that the donor receives a return."
The philosopher pressed further: "But what return? Your money is gone. The poor man has eaten it." Rabban Gamliel replied: "The return is not measured in coins. It is measured in merit, in divine protection, in the knowledge that you have participated in God's own work of sustaining the world. And because God is the guarantor, the donor can always give with a pleasant countenance — without resentment, without suspicion, without calculation."
This was the key: the pleasant countenance. The Talmud teaches that a person who gives charity grudgingly, with a sour face, loses the merit of giving. But the person who gives joyfully, trusting God to handle the outcome, receives full reward. Rabban Gamliel did not merely answer the philosopher's question. He revealed a system of cosmic economics in which generosity is always the safest investment.