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Natan uses his Rav as an agent to sell his chametz before Pesach. The rav sells the chametz to Jose.

On the 1st day of Hol Hamo'ed, Jingram stops by Natan's home and says that he is really hungry and needy and has no food for his family. Natan says, "I have a lot of stuff in my basement. The problem is that Jose owns it, so you have to ask him if he will sell it to you."

Jingram goes to Jose, and Jose says to Jingram, "I will give you the chametz for now, since you don't have money, but you need to pay me for this when you are able."

I assume that there is no problem with Jose selling Natan's chametz to whomever he wants even without notifying the rav, as Jose owns it and can do what he wants with it.

Pesach is over, and the rav buys the chametz back from Jose, and pays him back the amount for all the Chametz. Problem is that Natan's chametz was given to Jingram, and Jose should be paying that part back to the rav.

Jose tells the rav that he gave Natan's chametz to Jingram and Jingram hasn't paid him back. Jose is short on cash, too, so he can't pay back the rav that part either.

Now that Pesach is over, can Natan use his chametz if it hasn't technically been bought back? Can the rav excuse the debt completely or "postpone" the debt saying, "I'll deal with Jingram separately and he can pay me when he is able." Would that scenario allow Natan to eat his chametz?

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    Your question doesn't make sense now. The rav shouldn't pay for all the chametz he originally sold, just what's left. Anyway, Jose does have money because the Rav just paid him more than was owed. In any case, Natan's chametz has been more than bought back, so what's the problem? – Daniel Mar 26 '15 at 15:35
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    typically, the purchaser only gives a downpayment before the holiday, which is returned afterward. Jose would have to pay the full value of the chometz to the rav if he was taking possession of it afterwards. In this case, they could designate that part of the downpayment be applied to the value of the chametz Jose gave Jingram from Natan's stash. Jingram directly owes money to Jose. – Isaac Kotlicky Mar 26 '15 at 15:40
  • @IsaacKotlicky - sounds like a good answer ;-) – DanF Mar 26 '15 at 15:43
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Typically, the purchaser only gives a downpayment before the holiday, which is returned afterward.

Jose would have to pay the full value of the chometz to the rav if he was taking possession of it afterwards.

In this case, they could designate that part of the downpayment be applied to the value of the chametz Jose gave Jingram from Natan's stash. Jingram directly owes money to Jose.

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