1) WHICH SELLER IS A LOSER?
QUESTION: The Mishnah teaches that the prohibition of Ona'ah applies both to a seller (who may not overcharge) and to a buyer (who may not mislead the seller to undercharge). The Gemara derives this from the verse, "And when you transact a purchase to your friend, or acquire from the hand of your friend, you shall not defraud one another" (Vayikra 25:14). The Gemara explains why it is necessary for the Torah to explicitly include both a seller and a buyer in this prohibition. Had the Torah taught only that a seller may not overcharge, one might have thought that the Isur of Ona'ah applies only to a seller because a seller knows the correct price of the merchandise he sells. A buyer, however, who is not familiar with the value of the merchandise perhaps is not prohibited from underpaying. On the other hand, had the Torah taught only that a buyer may not underpay, one might have thought that the Isur of Ona'ah applies only to a buyer, since every buyer gains when he purchases merchandise. A seller, in contrast, is considered as though he loses when he sells his object (because he receives in return cash, which will quickly be consumed by his expenses). The Torah therefore must teach that both a buyer and a seller are subject to the Isur of Ona'ah.
The SHITAH MEKUBETZES quotes the RA'AVAD who asks that the Gemara's statement that a seller always loses when he sells seems imprecise. Granted, a person who sells family heirlooms or items dear to him because of lack of funds feels a sense of loss when he sells his items. However, such a seller cannot be the subject of the Gemara here when it says that the verse is needed to teach that the Isur of Ona'ah applies to the seller, because the Gemara earlier states that when an ordinary layman (Ba'al ha'Bayis) sells his personal items, he is not bound by the laws of Ona'ah! The Gemara cannot be referring to all other sellers (i.e. ordinary merchants), because their business is to buy and sell constantly, and they feel no loss when they sell their wares. To whom does the Gemara refer when it says that the seller feels that he loses when he sells, and yet the Isur of Ona'ah still applies to him?
(a) The RA'AVAD answers that the Gemara earlier does not mean that a Ba'al ha'Bayis is allowed to overcharge Ona'ah. It means merely that a Ba'al ha'Bayis is not required to give back the money he overcharged. The Gemara here addresses the case of the Ba'al ha'Bayis and says that without a verse explicitly stating that a seller cannot overcharge, one would have assumed that the Ba'al ha'Bayis who sells his possessions is not bound by the laws of Ona'ah at all and is permitted to overcharge.
(b) Alternatively, the Ra'avad answers that the Gemara refers to a Ba'al ha'Bayis who sells clothing which is made to sell (and not his precious possessions). The Gemara earlier quotes Rav Chisda who says that in such a case a Ba'al ha'Bayis also is prohibited from overcharging.
(c) The CHESHEK SHLOMO similarly answers that there are two different types of sales that a Ba'al ha'Bayis will make. One is a sale in which he merely wants to buy one item in order to receive money to buy a second item. Another type of sale is one in which a Ba'al ha'Bayis is in financial stress and he sells his possessions for cash. The Gemara earlier which says that Ona'ah does not apply when one purchases from a Ba'al ha'Bayis clearly refers to the first type of sale, in which the Ba'al ha'Bayis has the liberty to demand a lot of money for his possessions. As RASHI there (DH mi'Ba'al ha'Bayis) explains, everyone knows that a Ba'al ha'Bayis charges a lot of money for his precious possessions, and one who buys from him certainly knows that he is paying more than the actual value, and he does so with the unspoken condition that he will not claim Ona'ah. In contrast, in the second type of sale, a Ba'al ha'Bayis facing financial hardships will often accept less money for his possessions than they are actually worth, since he is desperate for money. No buyer will think that the Ba'al ha'Bayis is overcharging, and thus if he does overcharge the buyer has the right to claim Ona'ah and get his money back. It is this type of Ba'al ha'Bayis to whom the Gemara refers when it says that one might have thought that the seller is not bound by the prohibition of Ona'ah. The verse teaches that he, too, may not overcharge his buyer. (Y. MONTROSE)
2) ONE WHO MAKES A CONDITION THAT THE LAWS OF "ONA'AH" SHOULD NOT TAKE EFFECT
OPINIONS: The Gemara teaches that if the seller says to the buyer, "[I am selling to you this object] on condition that you do not claim Ona'ah from me," the buyer cannot claim Ona'ah. If he says, "... on condition that there is no Ona'ah in the object," the buyer may claim Ona'ah.
What is the reason for the difference between these two cases?
(a) RASHI (DH she'Ein Bo) explains that "there is no Ona'ah in the object" means that the buyer agrees that he will not claim Ona'ah because the price he is being charged is correct and he is not being overcharged. If he indeed is cheated, the law of Ona'ah applies because the seller's words were not true; there was Ona'ah in the object. The buyer may claim that the sale was a "Mekach Ta'us" (mistaken sale) and he may cancel the sale. In contrast, when the seller says "on condition that you do not claim Ona'ah from me," the buyer consciously foregoes any monetary claims associated with being overcharged.
TOSFOS (DH Al Menas) questions this explanation from the Gemara in Makos (3b). The Gemara there compares the case of Ona'ah with a similar case of a loan, in which the lender tells the borrower, "[I am lending to you the money] on condition that you will not cancel the loan in Shemitah," in which case the condition takes effect and the borrower must pay back the loan even after the Shemitah year has passed. If the lender says, "... on condition that the Shemitah year does not cancel the loan," the condition does not take effect and the Shemitah year does cancel the loan. Tosfos points out that the reason for the difference in those two cases is that in the first case the lender asks the borrower to waive his right to cancel the debt, but in the second case the lender attempts to override the Torah's law and say that the Shemitah year will not cancel the debt. The fact that the Gemara there compares the cases of Shemitah with the cases of Ona'ah implies that a similar logic applies to both. However, the logic which Rashi presents here to explain Ona'ah does not apply at all to Shemitah. Why, then, does the Gemara in Makos compare the cases?
Tosfos answers that according to Rashi, the comparison is not in the logical reasoning, but rather the Gemara simply compares two topics with similar phraseology.
(b) Tosfos quotes the RASHBAM who explains that the cases of Ona'ah and Shemitah indeed are similar, both in their phraseology and in their logic. The condition of "that there is no Ona'ah in the object" does not take effect because the Torah says that there is Ona'ah in an object when a person overcharges. The same reasoning explains why a lender cannot say to a borrower that he is lending money "on condition that the Shemitah year does not cancel the loan."
In the case of "on condition that you do not claim Ona'ah from me," the buyer does the same thing that the borrower does in the case of "on condition that you will not cancel the loan in Shemitah." Just as the borrower commits to pay back the loan even after Shemitah has cancelled the original loan, the buyer commits not to exercise his right to claim Ona'ah. The condition does not directly conflict with the word of the Torah. Rather, the buyer or borrower merely makes his own, personal monetary commitment. The Gemara in Makos compares these cases because they indeed are similar. This is also the explanation of the NIMUKEI YOSEF. (Y. MONTROSE)