Maharal (end of Nesiv haTzedakah) explains that tzedakah is not just about providing the needs of the poor – it’s not about the recipient. The purpose of the mitzvah of tzedakah is to engender a feeling of camaraderie within Klal Yisrael; we are all brothers and sisters. The way to do that is by giving to each other. If there are no poor to give to, then give to others who may not need it as much – just keep giving to each other.
There is another strange halacha in hil. tzedaka that we learn from our parsha. Chazal (quoted in Rashi) tell us that if a person was rich and then is forced to accept charity, it’s not enough to give him what it takes for bare bones survival. You need to give him what he was used to having. The millionaire who loses it all in a stock market crash needs to be given a limo with a driver, a nice suit, etc., not be forced to take a bus and buy his clothes at Walmart. How can it be that someone who is taking charity gets to live better than most of us who are working?
Rav Wolbe in his Alei Shor explains that this din reveals to us that true tzedakah is all about empathy. Of course a person can survive taking the bus to the shopping center and wearing clothes from Walmart. He doesn’t really suffer physical or material want. But think about what that millionaire who used to have a limo and wear $2000 suits feels when he is forced to do that! For you that pair of Walmart pants may be perfectly fine, but that millionaire feels completely crushed when he puts them on. Tzedakah means being able to put yourself in that millionaire’s shoes and feel his pain. It’s not just about physical want. Even if you would not feel lacking were you in the same situation, since he feels lacking, since he feels crushed, you have a mitzvah to help him.
The last point I want to touch on is the amazing din of “lo yeira levavcha b’titcha lo,” that you can’t give tzedakah begrudgingly, with a sour face. R’ Shapira in his ma’amarim on the parsha points out that there is an idea of doing all mitzvos b’simcha. Why do we need a special din here not to feel bad about giving? Apparently here it’s just an added hidur on top of the mitzvah, but it is part and parcel of the tzurah of the mitzvah itself. Here’s how R’ Simcha Bunim m’Peshicha fulfilled this din:
R' Simcha Bunim once told his chassidim that he wanted to spent Shabbos at a certain poor person’s home. So the chassidim got to work and it was like an episode of Bob Villa’s “This Old House.” They cleaned up that poor person’s house, they replaced his table with a table that a Rebbe could use for a tisch, they replaced his plates and utensils with plates and utensils fit for a Rebbe, they overturned his whole house until it became like palace. After Shabbos, R’ Bunim came to this poor Jew and said he wanted to give him some money for the mitzvah of tzedakah. The poor person was in shock. He said, “Dear Rebbe, since you decided to spend Shabbos here my home has been turned into a new home, my table is a new table, my dishes, my furniture, my silverware are all new – everything is beautiful. You now want to give me tzedakah on top of that?!”
R’ Bunim told him yes. He told this poor Jew that all that was done before was because every time he saw this person in poverty, he felt bad. “None of that was for you,” said R’ Bunim. “It was for me, so I wouldn’t feel troubled when I saw you. But now that you have a proper home, a proper table and chairs, proper silverware and dishes, I no longer feel bad. Now that I've fulfilled ‘lo yeira levavcha,’ now that it’s no longer about me and my feeling bad, I can fulfill the ‘b’titcha lo’ and give you real tzedakah.”