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The idea of the sale of chametz is based on the Gemara in Pesachim 5b:

It is said: “Neither shall there be leaven seen unto you” (Shmeot 13:7) – your own you must not see, but you may see that belonging to others and to the Most High.

          This passage implies that the Torah did not forbid the physical presence of chametz in a Jew’s home, but rather the possession of chametz belonging to him. The Gemara continues:

One might think that one may hide [chametz] or accept bailments [of chametz] from a non-Jew? Therefore the verse states: “It shall not be found [in your houses]” (Shemot 12:19)

The Gemara’s implication is that a Jew is permitted to have in his house chametz belonging to a non-Jew, but he is forbidden to accept responsibility for its safekeeping, such that the chametz would be in his possession as a deposit. 

     The Mishna in Pesachim 28a also deals with the sale of chametz to a non-Jew:

Chametz belonging to a non-Jew which had been kept over Pesach is permitted for use; but that of a Jew is forbidden for use. Because it is said: “Neither shall there be leaven seen with you.” According to most Rishonim, chametz belonging to a non-Jew which had been kept over Pesach is permitted even to be eaten, and not just for use. Therefore, chametz that was sold to a non-Jew before Pesach is permitted after Pesach.

   The Gemara (21a) raises an objection against the words of the Mishna, “and he sells it to a non-Jew”:

This is obvious! It is to reject [the view of] this Tanna. For it was taught: Bet Shammai maintain: A man must not sell his chametz to a non-Jew, unless he knows thereof that it will be consumed before Pesach. But Bet Hillel say: As long as he [the Jew] may eat it, he may sell it.

          According to Bet Shammai, the obligation to destroy chametz begins thirty days before Pesach, and so a person is only permitted to sell chametz to a non-Jew during this period if he knows that the chametz will be consumed before Pesach. The Halakha has been decided in accordance with the position of Bet Hillel, who permit the sale of chametz for as long as benefit may be derived from chametz. Here too, however, there is no hint of repurchase of the chametz at the conclusion of Pesach.

THE SOURCE OF THE LAW

          The sale of chametz with the intention of repurchasing it after Pesach is explicitly mentioned in the Tosefta (Pesachim 2:6):

A Jew and a non-Jew who were traveling together by ship, and the Jew has chametz on hand – he may sell it to the non-Jew, or give it to him as a gift, and then repurchase it from him after Pesach, provided that he gives it to him as an absolute gift.

          This Tosefta requires discussion on two different levels: on the level of understanding the Tosefta, and on the level of the practical Halakha with respect to the case discussed therein. On the exegetical level, we shall deal here with two questions:

1. The Tosefta deals with the case of “a Jew and a non-Jew who were traveling together by ship.” Does the Tosefta mean to limit the sale of chametz to such a case? Perhaps chametz may only be sold in a situation that does not involve any planning from the outset.

There are Rishonim who state explicitly that it is only the incidental sale of chametz that is permitted, but selling chametz in a fixed and institutionalized manner is forbidden (Talmid ha-Ritva[1] and R. Amram Gaon]. Most Rishonim, however,do not limit the sale of chametz in any manner. Many Rishonim cite the Tosefta as is, and it is difficult to draw any conclusions as to whether the sale of chametz is limited to the case mentioned in the Tosefta or whether this case is only an example. The Rambam, for example, rules in Hilkhot Chametz u-Matza 4:6:

If a Jew and a non-Jew are traveling together by ship, and the Jew has on hand some chametz, and the fifth hour arrives, he may sell it to the non-Jew or give it to him as a gift, and may then repurchase it from him after Pesach, provided that he gives it to him as an absolute gift. What is the law governing a person who sold his chametz to a non-Jew in a manner that was not “absolute”? The Tosefta’s ruling may have been intended only lekhatchila, but if a person sold his chametz with the intention of repurchasing it after Pesach, perhaps the sale is valid, the chametz belongs to the non-Jew, and thus he does not violate the prohibitions of bal yera’e and bal yimatze, and he may derive benefit from the chametz after Pesach.

Alternatively, the Tosefta’s ruling may apply even bedi’eved, and if the chametz was sold in such a manner that is not “absolute,” it is forbidden after Pesach. 

When a person is responsible for chametz (even if he did not accept such responsibility upon himself), he is interested in its continued existence, and therefore he is obligated to destroy it. A similar case is brought in the Yerushalmi, Pesachim 2:2

“Neither shall there be leaven seen unto you” (Shmeot 13:7). There are Tannaim who teach: Your own you must not see, but you may see on the street. There are [other] Tannaim who teach: Even on the street… He who said: Your own you must not see, but you may see on the street – where he renounced ownership prior to its removal. He who said: Even on the street – where he renounced ownership after its removal.

It is possible to transgress the prohibitions of chametz even with chametz with which a person has only a certain connection, and not just with chametz that fully belongs to him, then a difficulty arises regarding the sale of chametz that is customary today: Does a person retain some connection to the chametz that he has sold to a non-Jew? If he retains a connection, he maybe violating the prohibitions of bal yera’e and bal yimatze (owning chametz on Pesach; and the prohibition of deriving benefit even after Pesach from chametz that had been owned by a Jew on Pesach.)

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