Responsibility for a Missing Diamond | Various Rabbis | Beit Midrash

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A beit din conferred with Rav Moshe Feinstein regarding the case of Shimon who borrowed Reuven’s diamond to see if he could interest a buyer, and if he was not interested, he would promptly return it. Reuven had to leave for an hour and so told Shimon to leave the diamond with Levi, from whom he would retrieve it upon return. Shimon gave a sealed envelope to Levi with the explanation of what was asked of him, and Levi put the envelope in a safe with his own diamonds. Four days later, Reuven and Shimon came to claim the diamond, but the envelope was no longer in the safe. Levi says that he thinks that he returned it earlier to Reuven or Shimon, whom he sees on a regular basis. If not, the envelope must have been stolen because he did not take it out for any other reason. Reuven and Shimon are sure that they did not receive the envelope back from Levi.
Although one who certainly received something and is not sure if he returned it is obligated to pay if his counterpart claims he is sure he did not receive it back, here Levi can still be exempt based on the possibility that it was stolen, in which case he would be exempt. Levi claims with certainty that the only possibilities are ones that exempt him. One could not have expected Levi to guard the envelope in question better than he guards his own diamonds, especially when he was told that Reuven would claim it in an hour. Although he does not claim conclusively that the envelope was stolen, this is common for claims of theft made by one who watches an object and was not negligent (e.g., when he forgot where he put something – see Bava Metzia 35a). He can surmise that if there is no other explanation for its being missing, it must have been stolen.
According to the classical halacha, Levi would have to swear that the diamond is not in his possession and that he was not negligent in watching it. If he would not be willing to swear, we must consider whether he can exempt himself with the claim that he did not see that there was actually a diamond in the sealed envelope. One might want to claim that since Levi saw that there was something in the envelope and it must have been worth at least a peruta, he would be obligated to swear that it was nothing more than minimal value. If so, since he does not know what to swear, he is obligated to pay. However, in a case like this, in which Shimon knows that Levi was not expected to know what was inside, Levi would be exempt from paying more than the value he admits. On the other hand, Levi said that Shimon could swear what the value of the contents of the envelope was, and thus if he decided to do so, Shimon would be believed regarding the value.
In this case, then, Shimon would have to swear about the minimum value of the contents of the envelope, and Levi would have to swear that the object is not in his possession and that he was not negligent. The custom is not to swear but to "redeem" oaths by means of compromise that makes the one who should have sworn pay a third of the value in question. Unless beit din feels that another amount is more appropriate, Reuven/Shimon should lose a third by not swearing the value and regarding the remaining two-thirds, Levi has to pay a third for not swearing what he needs to. Therefore, the standard payment should be approximately two ninths of the claimed value of the diamond.