Charity must be given with an almost illogical insistence, but this must be joined by a prudent concern.
In Parashat Behar we are prohibited from taking interest (Vayikra 25:35-38). Rather, we are told, when "your brother" begins to fall you must "hold onto him" (Vayikra 25:35). This is one of the sources of the mitzva to give charity. The verse ends with the additional qualification that the declining individual "shall live with you". Both the term "to hold onto", and the stipulation "he shall live with you", are in need of clarification. They seem to imply something concerning the nature of charity.
In Torat Kohanim the sages interpret this verse in a manner that reveals matters of great importance to us, relating to widespread issues in modern society. The first peculiarity, the phrase, "you shall hold onto him", is understood as suggesting a continuous and persistent action. Even if it is necessary to uphold the declining person repeatedly, we are commanded to provide support again and again. The commandment to give charity is not a one-time action of giving another a chance. Often, one that falls financially once, does not succeed in rehabilitating himself at the first opportunity. It is not our business whether the other is to be blamed for his repeated decline; we have an obligation to support him. Perhaps the poor individual does not know how to use intelligently the money and support that he receives; this, however, does not discharge you of your responsibility.
There is one exception to this rule. Often the declining individual is not only unsuccessful in using the support he receives in order to extricate himself from his sad situation, he even uses it to fall farther. In such a situation, the good intended helping hand becomes a catalyst in the spiraling cycle of self-destruction. Our sages understood this verse to relate to such a situation also: "perhaps even if you are causing him to be lost to bad influence? Therefore it says: 'with you'."
The aim of your continuous and repeated support must be for the weak individual to "live with you". As elsewhere in the Torah, "with you" is understood to imply a closeness and identification. The care one gives must be aimed at rehabilitation; the goal must be for the poor to be integrated into society. While one must provide support even if this objective is not fulfilled successfully, one must ensure that it is not being undermined.
We are obligated to never leave the declining, but return almost illogically to support one that cannot untangle himself from his troubles. This must, however, never become an act of simplistic apathetic piety. One must ensure that the assistance does not become an added aspect of the individual's fall. Charity must be given with an almost illogical insistence, but this must be joined by a prudent concern.