Adapted from: What if… Volume 4 by Rabbi Yitzchok Zilberstein

וַיֹּאמֶר בָּא אָחִיךָ בְּמִרְמָה — — But he said, “Your brother came with cleverness” (Bereishis 27:35)

Q: Nachum is a very successful businessman who received a tip as to where he could purchase very special matzos for Pesach. Not only were the matzos baked by an expert team of bakers to ensure their kashrus for Pesach, but they were also unusually crisp and delicious. When Nachum asked the owner of the bakery how much the matzos cost per pound, the man quoted him an exceptionally high price. Nachum understood that the price had been set according to what the man assumed Nachum could afford, and Nachum refused to be the victim of extortion.

Nachum decided that he would send someone else in his place to purchase the matzos he needed. When Shmerel, one of Nachum’s workers, trudged into the bakery in his worn-out, faded suit, the owner sold him the matzos for half the price he had quoted Nachum.

The next day, Nachum wondered if he had acted properly, since had the bakery owner known that the matzos were really for Nachum, he never would have agreed to sell them at the lower price.

A: Rabbi Aharon Dovid Dunner was asked a similar question, and he responded that the wealthy man was entitled to act as he did, as is evidenced from the following halachah:

The Shulchan Aruch discusses the case of someone who wanted to buy a certain property, so he consulted one of the neighbors who owned an adjacent property. The neighbor advised him to make the purchase. After the purchase, the neighbor may claim that since he owns the adjacent property he has first rights to buy it, and the purchaser would have to sell it to him. This is despite the fact that the neighbor himself advised the purchaser to buy the property.

The Sma explains that the neighbor did not lose his right to buy the field, because he can clarify that the reason he counseled the purchaser to buy the field is because he wanted the field to be sold for a fair price. Had he attempted to buy it himself, the seller would have hiked up the price, because the field is really worth more to the neighbor than to anyone else.

Just as the neighbor is permitted to orchestrate matters so that someone else will purchase the property for a fair price and thus avoid having the seller take advantage of him, Nachum could send Shmerel to purchase the matzos at a fair price and avoid having the seller charge him excessively.

Rav Zilberstein humbly argued with the comparison. In the case of a bar metzra (the owner of an adjacent property), there is a halachic obligation to offer the property for sale to one’s neighbors before offering it for sale to others, for the same price that he would sell it to anyone else. Thus a neighbor may “send” someone else to buy it for him if he fears that the seller may try to take advantage of the situation. That halachah would not apply to the owner of the bakery, who is not obligated to sell his matzos to Nachum. Perhaps in such a case Nachum cannot send an indigent to buy the matzos in his stead.

It would seem that the answer to the question would be dependent on whether the baker is trying to take advantage of wealthy customers, in which case he is guilty of an aveirah. The Gemara in Succah relates that Shmuel would threaten the merchants who sold hadassim for Succos to lower their prices so that the mitzvah would be available to all. In such a situation, Nachum could send Shmerel to purchase the matzos on his behalf. If, however, the baker sells to wealthy people for a fair price, but he sells to poor people for a discounted price, it would be forbidden for Nachum to ask Shmerel to buy matzos for him.