| Rav Chaim Weg
Answer: The Shulchan Aruch says that if an owner misrepresents the value of an item that he gives a Shomer to watch, and the Shomer later discovers that the object in his care was worth more than what he thought, he is only responsible for the amount that he thought the item was worth because that is all that accepted responsibility for. He says an example of a Shomer who was told that he was watching a silver coin but later discovered that it was actually a gold coin. Since he only accepted responsibility for a silver coin, he is only liable for the value of such a coin.
In the case in question, the father of the kallah indicated that the envelope only contained money for one wedding, so he only accepted responsibility for that amount; therefore, he definitely is not liable for anything more than that.
Furthermore, since Reuven is watching the envelope for free, he is a Shomer Chinam, which means that he is only chayav for peshia. It is debatable whether putting money in a jacket pocket would be considered negligent because it would have been better protected in a pants pocket with the button closed. However, the Pischei Teshuva says that if the owner clearly sees where a Shomer plans on keeping an object he entrusts with him and he does not protest, it is understood that he accepted this type of shemirah and agreed to it. In this case, since Shimon saw Reuven placing the money in his jacket pocket and did not protest, we understand that he accepted this shemirah; therefore, Reuven cannot be held liable at all for the loss of the money.
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