“…Open your hand generously to your brother, to your indigent, and to your destitute in your land.” (Devarim 15:11)

I was recently given a ride by a friend of mine. I have noticed over time that he tries very hard to give rides to whomever he can. There is one “regular” passenger who usually goes to one of two destinations in the same city. My friend usually asks him “Where to today?” well before he needs to turn onto this road or that road. I found this to be a little bit strange, but never commented on it. Most drivers would ask such a question when they came closer to the point where they had to decide which way to go. The reason for this behavior was revealed to me incidentally.

But first I would like to ask a question on a story that I saw in a sefer. A rich man became very poor, and the Vilna Gaon was asked why this happened. He answered that it was because the man gave more than a fifth of his money to tzedakah. Chazal say that one should give a fifth, and giving more is improper.

However, the Rambam in the beginning of Meseches Pe’ah says that if one wants to be exceedingly pious, it is permitted to give more than a fifth of one’s money to charity. In addition, the Rambam (Yad Hachazakah 10:2) says that a person should never hold back from giving tzedakah, and nothing bad or damaging will happen to him because of the tzedakah that he gave. This seems to indicate that even if one gave more than a fifth nothing bad would happen to him! Furthermore, the Shita Mekubetzes (Kesuvos Daf Nun, based on Rashi) says it is also permissible to give more than a fifth to support Torah.

It is well known that the Divrei Chaim never went to sleep with any money in his possession. If he had money when it was time to go to sleep, he would find a poor person to give it to. When he was asked about the halacha which states that you should not give more than a fifth, he answered, “That is talking about a person who is just giving tzedakah to fulfill the mitzvah of tzedakah. But the Torah teaches us that if a person has sinned, part of the repentance process is to give tzedakah. Therefore, since this is for my personal “pikuah nefesh” and to obtain atonement, the halacha of one fifth does not apply.”

We have the Gaon who said you cannot give more than a fifth, but many others who seem to say that you can give more than a fifth.

In order to resolve this contradiction, I would like to suggest the following. There are wealthy people who feel they have the right to throw around their money frivolously. That is the concept of a mevazbaz (one who squanders) – just because one has the means, does not give him the right to spend thoughtlessly. However, if a person has a reason or a need, such as to further Torah or to redeem himself from sins, that is not considered squandering, and therefore it is permissible.

Similarly, if the person spends the extra funds specifically because he would like to increase his piousness, that is also called “money well spent.”

There is a well-known Chazal on the mitzvah of tzedakah, which states that one should give and give again – even 100 times. This is learned from the verse “pose’ach tiftach”, a double expression of giving. The concept is that when there is a need, one should fill it. The person should understand that being a giver is a special honor bestowed on him by Hakadosh Baruch Hu, and every time is a new privilege.

There are two expressions describing charitable people, “ba’al chesed” and “ba’al tzedakah”. I believe these terms imply that these people understand that this is part of the power that Hashem has bestowed upon them and they should do their job well. Therefore, the ba’al tzedakah perhaps will be permitted to give more than a fifth, understanding that to be his job. The man that the Vilna Gaon was talking about was just giving away extra money, and that is incorrect.

My friend who gave me a ride is a b’aal chesed. Today he explained to me that the reason that he asks early in the ride where his “regular” passenger’s destination is in order to facilitate his picking up other passengers who need rides, so he can tell these people his destination, and they can quickly decide to come in or not. In short, he is looking to get the most bang for his buck because he considers it an honor to help out another Jew.

Sometimes when we are repeatedly asked to give, we have an urge to say, “I gave already (at the office)”. Others will say, “What a wonderful opportunity I have to be able to do this mitzvah again!” Let us strive to be of the latter.