The Gaon, zl, m’Vilna, posits that this pasuk is intimating the proper guidelines one must maintain with regard to giving tzedakah, charity. There is a marked difference between an open hand and one in which he bends over his fingers, thereby partially closing his hand. When the hand is open and the fingers spread out/apart, the difference in physical size between each finger is apparent. When the hand is bent, however, all of the fingers are even; they all look the same.
Chazal teach that the mitzvah of tzedakah demands that a person must be reinstated to his original standing. For example, a wealthy man who had been used to riding in a horse drawn wagon should not be deprived of this amenity – despite the fact that many other people are used to getting around by the power of their own two feet. Since this poor man had been used to the lifestyle of the wealthy, we must provide for him what he is lacking. In other words, there are degrees among the poor. When we support the poor man, we are not to look only at the here and now, but rather, to look back in time, when this man had been able to sustain himself in a lifestyle of which we only dream.
This is the pasuk’s message. The tzedakah that we give should be given with an open hand, acknowledging the various backgrounds of the poor who seek our support. Just as an open hand manifests the varied lengths of the fingers, so, should our tzedakah contribution be reflective of the poor man’s background. All poor men are not created equal. Some, at one point, have been quite wealthy. This should be taken into consideration.
Rashi notes the spelling of the word aniyecha, your poor, which in the above pasuk is spelled with one yud. According to the rules of grammar, aniyecha with two yuds refers to at least two poor men, while aniyecha with one yud is singular, denoting one simple poor man. Why does the Torah speak to the solitary poor, when, in fact, the halachos of tzedakah be directed toward the single ani, poor man?
Horav Shmuel David Walkin, zl, gives a practical explanation. We like giving to organizations, to groups, to programs, where it involves a multitude of people, who will benefit from our funds. When our money is going to help a single Jew who is in need; when the tzedakah is not exotic; when we will not receive a plaque or a double spread in the newspaper, we hesitate; we are not as forthcoming with our contribution. The Torah seeks to circumvent this problem by writing aniyecha with one yud, in the singular, so that we will remember that the single poor man who petitions our support is just as important as the organization which dispatches a talented fundraiser. We must consider the person in need, regardless of the lack of recognition that accompanies such giving.