The janitor poked his head through the doorway of Gavriel Herman’s office. 

“I use mucho Windex this week,” he said in his best English. “Need two, three more cases, yes?”

“Okay, Carlos,” replied Gavriel. “I’ll add that to the cleaning supplies order.”

Gavriel was the administrator of Yeshiva Ohel Avrohom. One of the myriad responsibilities of his position was the purchasing of all the different items needed to keep the yeshiva running smoothly, such as food, paper goods, and janitorial supplies.

He called his vendor, added three cases of Windex to his monthly order, then ordered new basketballs for the boys and colored chalk for the teachers. He ate his lunch while paying four bills. Then he joined an important four-way conference call, hired a plumber for an emergency leak, and dealt with an irate bus driver. By the time he locked his office and left the building, it was quite late, and he was exhausted.

“You look terrible,” was his wife’s greeting when he finally got home. “You’ve really been working hard. Don’t you have some vacation days coming to you?”

“Vacation sounds good!” replied Gavriel. “I would love to take the kids to visit your parents in London, but tickets are so expensive now.”

Mrs. Herman had a suggestion. “You use your personal credit card for all yeshiva purchases, and they repay you monthly, right? You’ve been accruing airline miles for every dollar spent over the years. You must have hundreds of thousands of miles in your account.”

“Hmm.” Gavriel considered the idea. “I’m not sure I have the right to keep the miles for myself, being that all the purchases were made for the yeshiva. I’ll discuss the matter with the principal tomorrow; he has extensive halachic knowledge.”

The following day, Gavriel visited the menahel’s office and posed his question.

Rabbi Berger had an answer for his administrator. “The Gemara Kesubos (98b) teaches that when an agent purchases something that has a fixed value, and the seller gives the agent extra merchandise (e.g. thirteen doughnuts for the cost of twelve) or gives a discount on the price (e.g. the seller only charges ten dollars rather than eleven), the agent and the principal split the profit.

“There is a dispute amongst the Rishonim about the rationale behind this ruling. According to Rashi and Ramban, since it is not evident whether the merchant intended to give the extra to the agent or to his principal (the one with the cash), they split it. According to Rif and Rosh, this halacha represents an enactment of Chazal that the two parties should split the profit since they both contributed to generating this profit. It is assumed that the extra was given because of the principal’s money and the relationship the merchant has with the agent.

“The practical difference between these two explanations is when the seller states explicitly that he is giving the extra to one of the two parties.  According to Rashi and Ramban, the merchant’s intent must be honored since his intent was clear, whereas according to Rif and Rosh, the enactment of Chazal would still be in force and the two parties must split the extra.”

“What does that mean for me?” Gavriel inquired. “Do I have the right to use the miles I’ve accrued?”

“Based on these principles,” Rabbi Berger replied, “It would seem that you should have to share the miles with the yeshiva, because you were acting as their agent when you made the purchases.  There is, however, a major difference between your case and the case discussed in the Gemara Kesubos.  In the Gemara’s case, the agent was spending the principal’s money. Consequently, there is an uncertainty who the merchant wanted to reward: the one with the money or the one with whom he has a relationship.  You were spending your own money here.  As such, you are both the agent AND the one with the cash!  All opinions would agree that you can keep the miles for yourself.”

Gavriel was very pleased with the psak.

His in-laws were even happier.

Q: I am purchasing a bedroom set second-hand. I have already paid the seller in cash and arranged to come by the next day to collect the furniture. Does either side still have the possibility of backing out?

A: In a famous statement, R’ Yochanan teaches that cash payment finalizes a transaction according to Torah law. (B.M. 47b) However, the Mishna (B.M. 44a) teaches that for transactions between Jews, the Sages revoked the effect of cash payment and enabled retracting until an act of transaction (kinyan) is performed. In the case of a bedroom set, this would require picking up or dragging the beds (C.M. 198:1).

Thus, both sides still have the legal ability to back out before the items are collected. The Sages strongly discouraged doing so, and imposed a curse (mi shepara) on one who does not uphold his commitment (204:1, 4). The sale can easily be made binding though performing a kinyan sudar, whereby the buyer hands his handkerchief or pen to the seller in exchange for title to the beds (195:1). Moreover, nowadays cash payment might be considered a kinyan based on the concept of situmta – common business practice.