The gemara quotes the famous statement of Shmuel that if reuven sells to shimon a shtar chov that says that levi owes him money, the sale is binding, but reuven has the right to be mochel the debt. There are 2 issues to discuss: 1. Why does Reuven have the right of mechilah even after selling it? 2. Does Reuven owe Shimon any compensation? 3. Does garmi require refund of the $ payed, or does it demand compensation for the value of the shtar?
1. The Ri"f and Tosaof hold that the entire concept of selling a shtar chov is only m'drabonon, but on a d'oraysa level Reuven remains the owner since he has no ability to actually sell the shtar. Why can't the shtar be sold on a torah level? Tosafos 77a (top) writes that since the property is not in the jurisdiction of Reuven, he has no ability to sell it, just as he has no ability to be makdish it. Tosafos seems to understand that there is no concept of selling the "right of collection", because it is not a tangible item. The only thing which can actually be sold is the property which is not yet owned by Reuven, therefore it is not a binding sale m'doraysa. R' Elchonon (B"B 513) points out that the difficulty with this approach is that our gemara says that through a matnas shehciv mei'rah the Reuven can transfer ownership to Shimon. But if the problem is that Reuven doesn't have the property and the "right of collection" isn't transferable, how can he transfer this through a matnas shechiv mei'rah? We must say that a shechiv mei'rah works like yerusha, where shimon steps into reuven's shoes, rather than transfering ownership like r' papa says on 148a.
An alternative approach as to why the seller retains the right of mechila is offered by the Ran in kesubos quoting Rabbeinu Tam but also seems to be the approach of the Rashbam here (although he doesn't use the lomdushe terms of shi'bud haguf and shi'bud nechasim, like the ran does). The only part of the debt that is transferable is the shi'bud or "right of collection" that Reuven has on Levi's property, but the shi'bud ha'guf that reuven has on levi cannot be sold to shimon. Since the shi'bud on the property is dependent on the shi'bud ha'guf which remains in the hands of reuven, he has the ability to be mochel.
2. The Rashbam writes that if Reuven is mochel, he must compensate Shimon by reimbursing the money he spent because of dina d'garmi, as if Reuven burned the shtaros that shimon had which would allow him to collect from levi. R' Elchonon (519) asks, when reuven burns the shtaros of shimon he is damaging him by destroying his evidence against levi, but is not impacting the actual rights of collection so he must compensate only as garmi for the damages of destroying the evidence. But when reuven is mochel he is actually exempting levi from having to pay at all, the damage is much more severe because he is not just taking away the evidence, but being maf'kiah the actual debt? R' Elchonon suggests that according to Rabbeinu Tam where he is being mochel what he actually owns i.e. shi'bud ha'guf, just that it is me'meila causing a loss of shimon's shi'bud nechasim, it makes sense that we consider it only garmi. But according to Tosafos that he is directly taking away from shimon the d'rabonon ownership of the debt, it should be regarded as an actual damage, not just garmi. Based on this, the Rashbam who seems to hold like Rabbeinu Tam, would be li'shitaso by equating this with burning the shtar of shimon.
3. R' Elchonon asks that according to Tosafos that garmi only requires Reuven to reimburse shimon what he payed, if reueven gave the shtar to shimon as a gift he shouldn't have to reimburse him at all. This makes sense if dina d'garmi is only rabbinic (tosafos 22b), but if it is d'oraysa then why shouldn't reuven have to reimburse shimon the true value of the shtar? I am not sure why R' Elchonon assumes that if reuven gave it as a gift, he wouldn't have to compensate shimon. It would seem more logical that he would have to compensate shimon the market value of the shtar which would normally be what shimon would pay for it, not the dollar amount of the contract. The major question is whether the dina d'garmi is mechayev Reuven to refund shimon what he spent because we consider him to have damaged shimon by taking that money from him (in which case he wouldn't have to compensate at all for a gift), or whether he has to compensate him by paying him the market value of what people would pay to buy this shtar from reuven?
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