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If one stole a hundred dollars in regular cash (e.g. no rare bill editions), and still has those bills, does he have to return those particular bills or can he return any hundred dollars?

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It may depend on the condition of the bills when he stole them and when he's repaying the theft. Shulchan Aruch, Choshen Mishpat 360:7 (from Bava Kamma 96b) states:

הגוזל מעות ישנות ושיפן וחידשן לא קנה שהרי מתיישנין וחוזרים כשהיו. גזל מעות חדשים וישנן קנה שאם יחדשם פנים חדשות הם

If one steals old coins, and polishes them to make them appear new, he hasn't acquired them [i.e., he needs to return the actual coins], because when they become old again they will look just like they did before [and the halachic principle is that only an irreversible change makes the object become the property of the thief]. But if he stole new coins and aged them, he has acquired them [and need return only their value], because even if he makes them look new again, it is [considered] a new "face" [entity].

Needless to say, if the coins are in the same condition as when he stole them, then there has been no change that would make them become his property.

Presumably, then, the same considerations would apply to bills.

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"Presumably, then, the same considerations would apply to bills." -- Not necessarily. One could argue that coins, at least in the times of the gemara, depreciated in value when they became aged. Not so with bills nowadays; no matter how old it is, every store must accept it, or at least the bank certainly will. –  jake Jun 4 '12 at 2:34
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I agree with @jake, and am writing to comment that (not only bills but) even coins now may well not have the same rules as coins earlier (and perhaps still in some places), since they lack intrinsic value and have only official face value. Nice find, R' Alex, but WADR I don't think it's relevant. –  msh210 Jun 4 '12 at 7:00
    
@jake: if anything, then, according to your logic, that would mean that one always must return the bills, because there has been no significant shinui. –  Alex Jun 4 '12 at 13:41
    
@msh210: same thing. Indeed, then, this would mean that this particular halachah is even more relevant: coins or bills must always be returned if they are still in the thief's possession. That said, I'm not sure that jake's and your distinction between olden days and today is valid; the real question is whether indeed old coins (that were still full weight, just used) had less value back then. I'll have to research further. –  Alex Jun 4 '12 at 13:42
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@Alex IIRC a distinction is made cuz money in their day had intrinsic value (the coin was actually 1 g of gold) while today its more along the lines of a shetar (it represents 1 g of gold) –  Baal Shemot Tovot Jun 4 '12 at 15:35
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