From a Jewish standpoint, whether we can justify our avoidance of giving tzedakah seems to be strange at the least, if not down right immoral. The Talmud (Baba Batra 9a) states that giving tzedakah is greater than all the other mitzvot. Deuteronomy 15:7-11 tells us that it is our responsibility to give enough to the poor to the point at which poverty no longer exists [in the Land of Israel]. However, it is anything but easy to adhere to the well-established custom of giving ten percent of one's earnings. People give all sorts of explanations as to why they avoid giving tzedakah.
In R. Elliot Dorff's book Tikkun Olam (p. 108-110), he actually gives such explanations as to how people shirk on giving tzedakah. Are the reasons people give justifiable or are they petty excuses to perpetuate their selfishness? Upon examining the reasons giving in Dorff's book, we can better answer the question.
1) "It's my money. I've earned it. Why should people who didn't work for it get any of my money? I'll do what I want with it." Having a job is a huge indicator of whether one is in poverty. 75% of America's poor are currently unemployed. Since a large percentage of the poor in this country don't work, resentment from those who work is not uncommon, and on some level, is understandable. Although Judaism comes with a healthy does of property rights and capitalist ethos, it also comes with a more distributive sense of justice than that of libertarianism. In Jewish thought, we find a middle ground between aestheticism and obsession with physicality (i.e., hedonism). Judaism takes the mundane and elevates it to the holy. Money is no exception. Rather than take the self-absorbed route of unadulterated greed, Judaism asks that a certain portion of one's assets are used to help out those in need. Judaism calls the individual to transcend the self, hence the more communal call of justice.
2) "It's demeaning to accept tzedakah." It depends on the situation. Begging, especially if "done for a living," is innately humiliating. It erodes self-worth and what it means to be "created in His image." However, if the tzedakah given is used to help an individual get back on his feet during his temporary stint, then it's much more acceptable.
3) "I might reinforce physically harmful behavior." If you give the poor cash, you very well could be perpetuating a drinking or drug problem. This is more of a common occurrence than we would ever care for, but it's no excuse to not give. If you find this potential to be disconcerting, you can always help out by either giving food or clothing.
4) "Giving tzedakah will encourage the poor to stay poor." This is one of my major gripes with tzedakah as a practice. If the premise behind giving tzedakah is to alleviate poverty, then it does not adequately, as an institution, perform its function since it is not addressing root causes. Giving money disincentivizes poor individuals to look for work and stand on their own two feet in order to escape poverty. With the ever-prevailing mentality of self-entitlement in this country, it becomes all the more difficult to have this not be a worry. Any tzedakah [program] should entail incentives to get poor people to find employment and stand on their own two feet. The Talmud (Baba Batra 116a) states that if you had fifty plagues on one side and poverty on the other, poverty outweighs the other fifty plagues. We should do our utmost to get people out of poverty, which is why the highest of Maimonides' Eight Levels of Tzedakah (MT, Laws of Charity, 10:7-14) is giving someone a loan in which they can be self-reliant.
5) "I might be duped into giving to a fraudulent case." Rabbi Chayim Halberstam, better known as the Sanzer Rebbe, said that he'd rather give to a hundred fraudulent cases for every legitimate case rather than deprive that one legitimate poor person. I find that attitude to be highly counter-productive to the purpose of tzedakah. The primary purpose is to help the poor, which is why giving tzedakah even for an ulterior motive is still acceptable (Pesachim 8a-b). If this is of concern, I would advise the following. On an individual level (e.g., a single beggar), give non-cash options such as food or clothing. On an institutional level, do your research prior to giving so you can avoid giving to an institution that does something like give an exorbitant amount on fundraising or salaries for the higher-ups (see here and here). Skepticism about fraud makes one more cautious, but it's no reason not to give at all.
6) "I might get mugged if I give to a beggar." Especially if it's at night, a beggar can take advantage of your giving nature and decide to rob you, especially if they are on drugs. To avoid this scenario, either give in a safer zone (e.g., with people around) or give tzedakah to foundations that help with the poor.
7) "I don't know to whom I should give. There are too many people in need." Pirke Avot 2:16 says that you are not going to finish your task, but that does not mean you should desist from it. We are individuals with limited spheres of influence and limited resources. Just because you single handedly cannot fix poverty does not negate one's responsibility to give tzedakah.
Conclusion: A large majority of these concerns are valid, and should treat them as such. Although they give us reason to hesitate or limit the scope, it does not absolve us to give tzedakah. The current way we approach tzedakah can use some re-vamping. We first need to give tzedakah not just with the intention of doing good, but actually doing good, as opposed to giving to fraudsters. While we need to worry about providing poor people with food in their bellies or a roof over their head so they can survive the next day, we more importantly need to focus on why poverty exists in the first place. By creating programming that focuses on root causes (e.g., employment, education), we can head in a direction in which the amount of poor people decreases to the point of non-existence.
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