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As codified in, e.g., Mishna B'rura 450:24, it's forbidden to put oneself in a situation that he desires the continued existence of chametz on Pesach because its nonexistence would cause him some loss.

Most Jews nowadays sell our chametz at a fair market value (or so) before Pesach and buy it back after Pesach. Thus, if it is lost on Pesach, we will get paid for it by its owner; so we don't desire its continued existence. However:

  1. Suppose someone has (lo alenu!) a house fire or other loss, and his chametz is destroyed on Pesach. Will he really be paid for it by the gentile purchaser: is that what's done in practice? (Surely such a situation has come up.) And if not, then it seems he's desirous of the chametz's continued existence, since he'll incur loss if it's lost.
  2. What about chametz with sentimental value? Can one sell that before Pesach? After all, he seems to desire its continued existence.

Do any pos'kim discuss these issues?

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The second question is discussed in a Teshuva here by Rabbi Yoel Brach. The question under discussion is a business that buys a bunch of Chametz inventory right before Pesach and then does the traditional Mechiras Chametz.

On the question of that clearly the business wants that inventory to exist, he says a few points, prefaced by the fact that Chametz owned by a non-Jew, on the property of a non-Jew, is explicitly allowed in Shluchan Aruch to be under a Jew's responsibility (that is, if it is lost, the Jew has to pay for it - [this part actually address the first question, even though the Jew is responsible for losses, that is still OK, although as he goes into it, it is necessary to make the sale in such a way that the non-Jew rents the space where the Chametz is, which is pretty standard practice, AFAIK]), thus showing that the Jew wants the Chametz to remain:

  1. One answer is that it is only a problem if he benefits from the Chametz proper (unlike Idolotry issues), on Pesach (this has two variation, either because he is getting paid, or because the Chametz preserves his vessels).

  2. Others hold that as long as no action is taken with the Chametz, it is not a problem.

  3. Some hold explicitly that since the Chametz is sold before Pesach, there is no issue with HaRotzeh BeKiyumo (with some dispute if the sale can happen Erev Pesach - so that isn't of help for the standard Mechiras Chametz case except according to some).

  4. But there are still opinions that hold it is a problem. However, all agree that after Pesach it is not an issue of Chametz Sheavar Alav HaPesach.

He then goes on to discuss Chametz of sentimental value.

  1. He brings reasons to say that a sale doesn't help, even according to the majority of Poskim who think a standard pro-forma sale of Chametz is completely legitimate.

  2. He brings opinions that this would run afoul of HaRotze BeKiyumo more so than standard Chametz.

  3. He brings a "weak" (his word) justification for selling such sentimental value Chametz in that the person has no intention of ever eating it, so it is already "botul".

  4. Along the lines of that justification he talks about sealing the Chametz away to the point where it wouldn't be accessible. Then, according to that idea, it wouldn't even need to be sold.

  5. (Not in this Teshuva, but I have heard of another solution to the sentimental value Chametz problem - leave it in a hefker place and make it hefker - and hope no one takes it - not sure how that would play out vis-a-vis Rotzeh BeKiyumo, I guess it isn't worse than selling it before Pesach (point #3 in the other section above)).

So the upshot is that the sentimental value Chametz is better off burnt and derive the sentiment from the ashes.

(On the question in the Teshuva, he says to be strict and not do it unless there is a specific great loss or difficulty - comparing it more to the sentimental Chametz - because the business wants the inventory's immediate availability after Pesach and would not be happy if the sale actually completed).

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