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Case: Reuven sent his agent (Shimon) with a loan contract to receive payment from the borrower (Levi). Reuven told Shimon that if Levi does not pay, Shimon should not hand over the contract to his partner (Yehuda). At the end, Levi did not pay, and Shimon did give the contract to Yehuda. Yehuda did extract full payment from Levi and is refusing to give Reuven half the money because of the claim that Reuven owes him money from other transactions. Can Yehuda keep the money? Must Shimon reimburse Reuven for causing a loss by not following his instructions?
Ruling: Some local rabbanim argue that ostensibly Shimon should have to pay Reuven and, because of this, Yehuda will not be able to withhold Reuven’s half due to the damage it will cause Shimon (see Rama, Choshen Mishpat 58:1). Others say that since Shimon made a mistake regarding what to do with a document, we apply the Rama (CM 55:1), based on the Rashba, that when someone returns a loan contract to the creditor after payment, he is exempt from damage payment because it is gerama (indirect damage).
P'ninat Mishpat (827)
Various Rabbis
353 - A Partner in Crime’s Part in Returning Stolen Property
354 - An Agent who Gave the Document to the Wrong Person
355 - Document to Overturn Laws of Inheritance
Load More
While the above analysis fits the Masat Binyamin’s approach, this is actually a difficult opinion. Consider that the gemara (Ketubot 85a) obligates an agent who paid the creditor before taking the loan contract, which seems against the Rashba. The distinction must depend on who gave the document to the wrong person. A marginally related person can be exempt due to gerama, but someone who was given the document as a watchman or an agent and acts against the instructions or the interests of an interested party is considered a mazik (damager). Thereby, he is obligated even though the normal obligations of a watchman do not apply to contracts and the damage is indirect for others. [The Chatam Sofer explains why this category does not apply in the Rashba’s case, but it is too involved to present in this context.]
Therefore, in this case, Shimon would definitely be obligated to Reuven, and, therefore, Yehuda may not use the document as a tool to seize money that he claims Reuven owes him from a different situation. Rather, Yehuda should give Reuven his half of the loan from Levi, and Reuven should swear that he does not owe Yehuda.

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