Mr. Meyers scurried around the wedding hall, making sure that everything was properly in place; his son was getting married.

“Could you please watch this envelope?” he asked his close friend, Mr. Koenig.

“Sure,” Mr. Koenig answered, taking the envelope.

Toward the end of the wedding, Mr. Meyers asked his friend for the envelope. Mr. Koenig reached into his shirt pocket for it, but found nothing.

“I put the envelope in my shirt pocket,” he said. “It must have fallen out during the dancing. What was in it?”

“There was over $3,000 in cash to pay tips and other expenses,” Mr. Meyers said.

“You’re kidding me!” exclaimed Mr. Koenig. “You didn’t tell me there was money in the envelope.”

“I didn’t think it was necessary to tell you what it contained,” said Mr. Meyers. “Anyway, I assumed you would realize it was money.”

“I really had no idea what the envelope contained,” said Mr. Koenig.

“What, you don’t trust me?!” said Mr. Meyers. “I’m telling you there was over $3,000 in cash in there.”

“I’m not denying what you say,” apologized Mr. Koenig. “However, if you want me to pay, you need some evidence. Furthermore, I’m not sure that I have to pay the $3,000, since you never told me there was cash in the envelope!”

“I don’t see why not,” replied Mr. Meyers. “If you agreed to watch the envelope, you are responsible for whatever it contained.”

“On the other hand, I’m a shomer chinam (unpaid guardian),” argued Mr. Koenig. “I’m not responsible for loss in any case.”

“There are different kinds of loss,” countered Mr. Meyers. “Listen, Rabbi Dayan is here; we can ask him.”

When Rabbi Dayan saw them approaching, he greeted Mr. Meyers, “Mazel tov! What a beautiful simcha. May you merit to see true Yiddishe nachas from the couple!”

“Amen, thank you,” replied Mr. Meyers. “I have an issue here with my friend, though. Maybe you can help us.”

“Certainly,” offered Rabbi Dayan. “Sit down.”

The two sat down. Mr. Meyers related what had happened and claimed that Mr. Koenig owed him the $3,000 that was in the envelope.

“What a fascinating case,” replied Rabbi Dayan. “Let’s go through the issues one by one.

“Even an unpaid guardian is responsible if he lost the entrusted item through negligence,” he said. “Placing the envelope in a deep, secure jacket pocket would seem acceptable under the circumstances. However, placing it in a shirt pocket, where it can easily fall out, is considered negligence (Pischei Teshuvah, C.M. 291:5, 8).”

“What about the fact that I had no idea what was entrusted to me?” asked Mr. Koenig.

“If the owner misrepresented the contents, the guardian only has to pay the value of what he agreed to watch,” answered Rabbi Dayan (291:4). “For example, had Mr. Meyers told you it was just some receipts or a check, you would not have to pay the $3,000, even if he had evidence that it contained cash. However, if the contents were not specified, you accepted responsibility for whatever was inside.”

“But how do I know what was actually inside?” Mr. Koenig asked. “There’s no evidence at all! Do I have to pay without evidence?”

“If you trust the word of Mr. Meyers completely, you must pay even without evidence,” said Rabbi Dayan. “If you doubt his word, the Shulchan Aruch rules that when the guardian was negligent, the Sages instituted that the owner should swear what was entrusted and collect that amount, if reasonable (90:10; see Shach 90:16).”

“Does this apply also if Mr. Koenig knew that there was money in the envelope, but didn’t know how much?” asked Mr. Meyers.

“In that case, since the guardian admits partially and cannot swear about the remainder, some maintain that he must pay even without an oath by the owner, based on the rule of ‘mitoch she’eino yachol lishava meshalem’,” replied Rabbi Dayan. “Others maintain that this principle does not apply, though, since the guardian is not expected to know how much was inside, so an oath by Mr. Meyers is still required (90:10; 298:1).”