The Mishnah (9:8) discusses a case where one was entrusted with an object, then subsequently swore falsely that it was stolen. If witnesses testify that he really had the item, he will need to pay back kefel -- double its value. This is the same punishment for one that stole an object. Note however that this case is exceptional because if the custodian swore falsely that it was simply lost, then he would need to pay keren ve'chomesh -- its value plus an extra twenty-five percent. Importantly, this case is where the shomer was a shomer chinam; he was not being paid to look after it. Consequently, in both cases, the claim that it was either stolen or lost would have exempted him from compensation (provided he was not negligent in caring for the object). Our case is treated differently as outline by the Torah (Shemot 22:7-8).
The Gemara records a debate regarding the details of the case. According to Rav Chiya bar Yosef, the obligation to pay kefel is only if witnesses testify that he used the object for his own purposes (shilach bo yad) prior to making the shevua. R' Sheshet however takes the opposite position. We shall try to understand R' Sheshet's position.
Prior to R' Sheshet's opinion, R' Chiya bar Abba said that R' Yochana maintained that kefel will be obligated if the entrusted animal was untouched. The Gemara is unsure whether it is [only]{.underline} in that case (like the opinion of R' Sheshet) or [also]{.underline} in that case. The Gemara explains that according to the first understanding, kefel will only apply if he did not touch it, since as soon as he handles it for his own needs, he acquires it and the subsequent shevua has no effect. How do we understand this Gemara?
Rashi explains that as soon as he used the pikadon for his own purposes, he "acquired it" and it is considered his property. That is to the extent that no matter what happens, the value will need to be returned to the owner. Consequently, the false oath is being made to the current "owner", which is himself.
R' Akiva Eiger (Shut MK 192) finds this explanation difficult. Granted he is obligated to pay back, but it does not truly belong to him. Furthermore, the Gemara's reasoning that "the shevua has no effect" does not fit with this explanation.
R' Akiva Eiger explains that the straightforward explanation is that once he is sholeach yad, he is obligated to pay no matter what. Consequently, the shevua that it was stolen no longer exempts him from payment -- even if it were true. The obligation to pay kefel is only where such a shevua, were it true, would have exempted him from payment.
R' Akiva explains that Rashi's position is based on the Gemara's case where the custodian first swore (falsely) that it was lost, and then after swore that it was stolen. In that case he would be exempt from kefel. The Gemara's initial suggestion is that after the first shevua he acquired it. This sounds like Rashi's explanation and does not fit with the simple explanation R' Akiva Eiger presented above. Indeed R' Akiva Eiger concludes that both understandings would apply to exempt one from kefel.
The Zecher Yitzchak concludes from that same Gemara that it is not because the shevua does not exempt him, but rather because he is already defined as gazlan. He explains that as soon as he was sholeach yad he was obligated to pay keren (the principal value). When the Gemara says that the shevua would have no effect, it is because it cannot obligate him to pay keren since he is already obligated to pay. Furthermore, the kefel never comes about in two phases, only when it obligates keren as well. Consequently, in this case, we cannot obligate kefel.
The Zecher Yitzchak however cites the Rambam (Gneiva 4:3) who explains that the reason why he is exempt from kefel if he first swore it was lost and then swore it was stolen is because "the object already left the possession of the owner". Firstly, was find that the exemption has nothing to do with the efficacy of the second shevua. He therefore explains that for one to be obligated in paying kefel they need to steal the object from the property of the owner. If was no longer in the possession of the owner, then it would be like stealing from thief, where one is not obligated to pay kefel. Consequently, in this case, according to R' Sheshet once he is sholeach yad, it is no longer considered in the possession of the owner and the subsequent shevuah, would no longer be removing it from his possession so he is exempt from kefel.
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