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If a shoel (someone who borrowed non-fungible personalty) re-lent the borrowed item to a further borrower (which he may not do), the original borrower (i.e., the relender) is liable to the original lender for any damages that occur. (Shulchan Aruch, Choshen Mishpat 342, q.v.)

Does the relender then have a claim against his borrower for those damages? (Assume the item was not mesa mechamas m'lachtah. In a normal case of borrowing, not reborrowing, the lender would have a claim against the borrower.)

Likewise, suppose the original shoel gave the item to a shomer chinam (bailee). Again, the borrower is liable for damages to the lender, even if the shomer was negligent (poshea). (Or at least so it seems to me. For one thing, it's directly analogous to the above case. For another, it's pretty much implied by SA CM 72:31, which doesn't say it's referring to only a case in which the bailee was not poshea (and the nos'e kelim don't say so, either).)

If the shomer was negligent, does the borrower have a claim against him? (In a normal case of bailment, not of a borrowed object, the bailor has a claim against the bailee for negligence.)

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@msh210 Isn't this the general theme of Baba Metzia 35b? Why wouldn't we look at it as two independent cases: Owner with first borrower, and first borrower with second shomer? –  Michoel Oct 11 '12 at 8:51
    
@Michoel, if I ever learned BM 35:2, I did so only in fifth grade, and have by now long forgotten it. If that's the answer, then please post it as such! –  msh210 Oct 11 '12 at 15:26
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Shulchan Aruch CM 396:9 says (my own loose translation):

מסרו השומר לשומר אחר, והיזק - חייב; ששומר שמסר לשומר חייב. אפילו שומר חנם שמסר לשומר שכר, ואם הזיק - חייב השומר הראשון לשלם לניזק וילך לעשות דין עם השומר השני.

If a shomer gave the item to a second shomer and it was damaged - he is responsible; as the rule is that, "A shomer who gives over the item to another shomer is responsible". This is the case even if shomer chinam gave the item to a shomer sachar [thus resulting in a higher level of care for the object]. If the item became damaged the original shomer must pay the owner, and he must take it up with the second shomer.

This Halacha is also brought in 291:26, where from the context it is clear that shomer is not limited to a shomer chinam/sachar but includes a sho'el. The way the Halacha is summarized/explained in Pischei Choshen (Pikadon Vesha'ala Chapter 2 Seif 30) is as follows: If a shomer gives the item to a second shomer; if he was authorized to do so the owner deals with the second shomer, if he was not authorized to do so - the owner deals with the first shomer, and the first shomer deals with the second shomer.

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