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Answer: This is a case where halachic intuition screams from the outset that it must be permitted to use ma’aser money, as the money is being given with the intention to help Reuven. We now aim to provide specific reasons why the intuition is indeed correct.
We begin with a simple halacha. After a guarantor has, based on the agreed terms, paid the loan back instead of the borrower, the borrower is required to reimburse him (Shulchan Aruch, Choshen Mishpat 130:1). This halacha impacts on our question in two ways. First, on the practical level, the donors are extricating Reuven from debt, whether you view it as the present debt to the gemach, or the future one to the arev.
Perhaps more significantly, the above and other halachot are instructive in understanding the nature of the mutual obligations when a borrower is unable to pay and an arev is called on to do so. It is not that the arev turns into the borrower, as the borrower remains obligated. Therefore, if the donors pay, they will be paying and relieving Reuven’s debt. The fact that practically this will benefit Shimon greatly does not cancel the tzedaka toward Reuven.
Under certain circumstances, there are additional reasons. Let’s assume Shimon took the responsibility as a chesed (not for some personal gain) and planned that if Reuven would be unable to pay, he would count his payment of the loan as tzedaka/ma’aser, as he may (see Tzedaka U’mishpat 5:(50)). If so, if the new donors relieve Shimon of paying, they are saving money for Shimon’s ma’aser fund, which is in effect a donation to it. While we usually thinking of giving our ma’aser kesafim to poor individuals or official NPOs, one can give (or, as in the case, give, in effect) his ma’aser money to someone else’s ma’aser fund. Thus, even if one views it (incorrectly, in our opinion, as above) as giving money on behalf of Shimon, it could still be considered giving it to his ma’aser fund.
Another way of looking at the donation as a valid use of ma’aser is to simply look at the donors’ actions as replacing the existing guarantor. While one could claim that this was an unnecessary gesture, as Shimon does not need to be replaced, in the final analysis, the donors are paying for Reuven, as Shimon had been prepared to do. So if, as we posited, Shimon could consider his payment as a legitimate tzedaka outlay (even though he originally hoped not to), certainly the new donors, who are acting in at least as altruistic a manner as Shimon, can consider it such.
Finally, it may be possible to give the money as a donation to the shul’s gemach, as they are actually giving it, just doing so on condition that the gemach will let their friend "off the hook." This is not far-fetched. After all, the gemach is not interested, despite the requirement of an arev, in forcing payment from one with extreme difficulty paying. Rather, they are concerned that if they let people off too lightly, they will lose the ability to continue lending to others in the future. The new donors are assuring the gemach that they can forgive Reuven because the donors are replenishing their resources commensurately.
Thus, we have been able to find five constructs to support the intuitive conviction that the donors’ philanthropy should be considered a proper use of tzedaka funds. However, we would point out that the first two constructs are the most straightforward truths.
Bemare Habazak - Rabbis Questions (652)
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132 - Paying a Poor Person’s Guaranteed Loan from Ma’aser Money
133 - Raising Charitable Funds on Shabbat
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