Rav Chaim Weg
Answer: If Reuven is entrusted to watch an object, he must watch it himself. He is not permitted to give it to Shimon to watch in his stead. Even if the public considers Shimon to be more trustworthy than Reuven, he still is not allowed to entrust him with the object because the owner only trusted him with it. If he does give it to someone else and it is subsequently lost, he is liable to pay unless he can bring witnesses to testify that no negligence was involved in causing the loss.
However, there are several exceptions to this rule. Firstly, it is understood that when someone gives a man an item to watch, he may entrust it to his wife or adult children. Furthermore, it is understood that if someone lends someone an item, he may allow his adult family members to use it as well. Therefore, if someone lends a man a car, it is accepted that his wife or adult children may drive it.
Secondly, if Shimon is a person who the owner generally entrusts his possessions to, Reuven can assume that he allows him to entrust Shimon with an item that he was given to watch and he may give it over to his care.
The third exception is the type of person who usually does not watch items on his own, rather, he delegates responsibilities to others. In such a case, it is understood that he will give the item he is entrusted over to an underling to watch it. A CEO of a large corporation generally has secretaries that go to the bank for him. Therefore, it is understood that he will hand over money that is entrusted to him to his frum secretary which he is permitted to do. In conclusion, the man in this question did nothing wrong and cannot be held liable for the robbery.
Question: What If the secretary is not frum?
Answer: If it is known that this person generally gives money to someone who the Torah does not consider to be responsible, it could be argued that one who entrusts him with money does so at his own risk.
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