Question:
My grandfather used to always give beggars on the street a coin, and he would say it is better to give before you are asked. I am now realizing that many of his sayings were actually based on Jewish wisdom, and am researching the sources. Is there something about giving without being asked?
Answer:
Your grandfather was a mystic, even if he didn't know it.
The Baal Shem Tov taught that there is an extra power to charity when you give it without being asked. When the giver initiates a donation, it arouses divine kindness from above even more than when you respond to a request to give. Just as you gave an unsolicited gift, you will receive blessings from above that you didn't even ask for.
This is illustrated by the fact that G-d's name, the name that denotes divine kindness - Yud-Heh-Vav-Heh ה-ו-ה-י - is recreated when you give charity.
The coin that is given resembles the Yud ............................................................י
The five fingers of your giving hand are the Heh, the fifth letter in the alphabet.........ה
The arm reaching out to give resembles the Vav .................................................ו
And the five fingers of the poor man's hand receiving the gift is the final Heh...........ה
This only works when you initiate the giving. If you wait for the poor man to stretch out his hand to you, then G-d's name is jumbled, and the blessing is therefore delayed. That's why your grandfather didn't wait for the needy to come to him. A proactive giver gets G-d's name the right way up.
~ Rabbi Aron Moss