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Answer: There are three approaches to how to view to the halachic significance of giving a check. 1) Since it is generally forbidden to cancel a check, a check is like money (Igrot Moshe, Choshen Mishpat II:15). 2) A check is a self-obligation of the check writer (drawer), to the payee or to anyone if it is an open check (Minchat Yitzchak V:119); 3) The check is no more than an order that the drawer gives to a financial institution to give money to the payee (Shevet Halevi VII:222). The starkest difference between #2 and #3 is whether, if the drawer cancels the check, the obligation to pay still exists. (From a technical perspective, banks usually allow one to cancel the check, but the legal system needs to be convinced he was justified to do so.) #3 is definitely the direct meaning of the check. As they are used in today’s society, the more accepted approach is #2, that it is not considered money, but that the drawer obligates himself to pay whoever uses it legally (see Pitchei Choshen, Halva’ah 10:(21); Shirat Devora II, CM 23).
(Almost) all agree that if one gave a check to one whom he owed and it got destroyed, he has to replace it. Even if one conceptually views a check like money, it is significantly different from real money in this context. If Levi pays Yehuda with cash, the payment is immediately usable, whereas a check needs to be cashed or transferred first. More significantly, if Levi feels bad and wants to pay money again, it will be an outright loss for him. But if Levi writes Yehuda a personal check and it was destroyed, the money was never drawn from Levi’s bank account as planned, and Levi is no worse off than he planned (except the price of a check) if he writes another one. So, if Reuven did not transfer the check to Shimon, you should enable him to do so.
If Reuven already gave the check to Shimon, you could argue that since you do not owe Shimon, it is not your responsibility to make sure he receives the money. However, this is apparently wrong. The mitzva to return a lost object is not limited to physical objects but applies broadly to help someone out regarding his property (Shulchan Aruch, CM 259:9), and therefore enabling Shimon to use the check he received should be included. While it is true that one does not have to lose money returning a lost object (see Shulchan Aruch Harav, Aveida 33), and here you will be "out" 2,000 NIS, having money you were obligated to give taken from your account is not a loss (see Tosafot, Bava Kama 58a).
Even if we did not view a check as creating an obligation, if Reuven owed Shimon, then through a rule called shibudda d’Rabbi Natan, you, who owed Reuven, would be considered as owing Shimon (Shulchan Aruch, CM 86:1). Although the application here is complicated (see ibid. 2), it is wrong for you to divorce yourself from this obligation.
Bemare Habazak - Rabbis Questions (654)
Rabbi Daniel Mann
527 - Paying a Babysitter for Work on Shabbat
528 - Making Sure your Check Is Cashed
529 - Non-negotiated Fees
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