Case:The plaintiff (=pl) is a non-profit organization that provides an important service for certain Israeli communities. Def, an acquaintance of one of pl’s leaders, had a connection with a certain community that was serviced by pl. Pl claims that the community did not meet their normal criteria, and pl provided the service (costing $30,750) only because def promised to raise (or donate) a large portion to cover the costs. Def claims that he did not ask pl to provide the service to the community but that in response to pl’s request that he raise money for the project, he had promised to try. Def says that he has only limited contacts he could ask for donations for pl, which he exhausted, and he never obligated himself to do more than that.

Ruling:First we must decide the halacha assuming pl’s claim is accurate.
The expectation was that def would raise money from others rather than donate it from his pocket. Even so, if pl expended money based on def’s pledge to cover expenses, def would be obligated to get the money one way or the other. This is true even though def was not the recipient of the benefit, as one who hired someone to do work for his friend has to pay (Bava Metzia 118b). The Rashba (ad loc.) says that the obligation is based on arvut, the concept of a guarantor, who is obligated to pay the lender for money someone else received. Another possible legal construct for obligation is damage payments (see Shulchan Aruch Choshen Mishpat 333:8), but this seems to be the subject of a machloket between the Rambam and the Ra’avad (Z’chiyah 6:24), and it is unclear whether money can be extracted based upon it. Rabbi Akiva Eiger (I:134) says that all agree to damage payment if one explicitly requested of another to do something, although the Maharsham (VI:198) disagrees with that assumption. In this case, the fact that def had an interest in the service being provided to the community in question strengthens the logic for payment.
On the other hand, there is reason to exempt def even if he requested pl to provide the service, based on the concept of meshateh ani becha ("I was not serious with you"). One of the cases where this may apply is when one asserts he will pay a person whom he feels should be doing it for free. One example is when a father-in-law tells his son-in-law who is not spending money on their son/grandson’s education despite having means to do so (Rama, CM 81:1; 336:1). The reason is that the father should be paying for his son’s education, and the offer to pay could be an empty promise to try to get the other to do the right thing. In our case, pl usually provides their service for free, and therefore def could be seen as trying to get them to provide the same service for another worthy recipient, and def might not be serious about obligating himself firmly. However, we reject this claim considering that pl is not obligated to provide services to anyone specific. Therefore, def cannot have them do so for the recipient based on a hollow promise.