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Case: The plaintiff (=pl) introduced investors in real estate to the defendant (=def), who deals in such investments. The agreement between pl and def is that pl gets a finder’s fee of 1.5% of every amount invested based on his introduction. All agree that $240,000 was invested in this manner. Pl claims that he received a finder’s fee on only the first $50,000, and therefore is owed 1.5% * 190,000 = $2,850. Def claimed and proved that the first investment was $100,000, and therefore he certainly paid the fee on that. He remembers clearly paying the fee for the next $100,000 ($1,500). He does not remember paying for the last $40,000 ($600) but assumes that he did so as well. Def promised documentation on almost all of the payments, but did not follow through.
P'ninat Mishpat (829)
Various Rabbis
497 - Expenses of Using Hotza’ah Lapo’al
498 - Claims of Various Levels on Payment of Finder’s Fee - Part I
499 - Claims of Various Levels on Payment of Finder’s Fee – Part II
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On the $600 fee from the last $40,000 invested, we apply the rule (Shulchan Aruch, Choshen Mishpat 75:9) that when a defendant replies to a claim on a sum of money by admitting having owed the sum and being unsure whether he repaid, he must pay the amount in question.
Regarding the $1,500, the general rule is that if one owes money but there is no written document for it and he claims that he paid the debt, he is exempt from paying. He is only obligated to make a Rabbinic-level oath that he paid (ibid. 13). If he admits that he owes part of the sum claimed, he is obligated in a Torah-level oath to exempt himself from the rest (ibid. 2). The gemara (Bava Metzia 3a) reasons that a Torah-level oath is all the more appropriate if the defendant has to pay part of the claim due to testimony (see Shulchan Aruch ibid. 4). The Shulchan Aruch (ibid. 5) says that if he ostensibly denies owing money, based on an arithmetic mistake but proper arithmetic shows that his story is actually a partial admission, then he is obligated to make a Torah-level oath on the rest. The Rama (ad loc.), based on the Rashba, says that if the defendant did not admit at all, just that his claim was a losing claim in regard to part of the money, so that beit din makes him pay it, he still does not have a Torah-level oath on the rest. The Rambam (Gezeila 4:16) is also of that opinion.
In fact, the Shulchan Aruch (87:5) also takes the latter approach, in apparent contradiction to the above. The S’ma (75:19) answers the contradiction as follows. In siman 75, since the obligation comes from the defendant’s own words, it is considered like a partial admission, which creates the oath obligation, despite the fact that he did not intend to admit anything. In contrast, in siman 87, if we were to believe what the defendant said, he would not have been obligated at all, and therefore he is not treated like one who admits.
Next time, we will see other explanations and distinctions and apply them to our case in which def has to pay at least $600 despite the lack of a full admission or full testimony.

P'ninat Mishpat P'ninat Mishpat: Agricultural Water Rights – part I
based on ruling 84122 of the Eretz Hemdah-Gazit Rabbinical Courts

P'ninat Mishpat P'ninat Mishpat: Multiple Agreements and Parties – part IV
based on final ruling of 80082 of the Eretz Hemdah-Gazit Rabbinical Courts

P'ninat Mishpat P'ninat Mishpat: Smoking Rights in a Rental? – part III
based on ruling 85076 of the Eretz Hemdah-Gazit Rabbinical Courts
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