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Answer: Your actions and questions show noble concern for both your fellow man and the honor of Hashem, and it is a pleasure to analyze halachic elements you raise. There are troubling educational and societal issues in this scenario, as you understand it, but we will suffice with what you asked.
The gemara (Nedarim 33a) says that one who pays his friend’s debt is not considered giving his friend positive benefit but removing an obstacle (this makes a difference regarding nedarim and whether he can demand compensation from the debtor (see Ketubot 107b)). However, it is a given that the debt is considered paid, precluding the creditor’s further demands on the debtor. How payment by a person other than the debtor or his agent works is an important question. One possibility is a concept known as eved k’naani (Kiddushin 7a) –when Levi gives something to Yehuda on behalf of Naftali, it counts as if Naftali gave it (Chazon Ish, Even Haezer 36, p. 237). Another possibility is that there is an implied stipulation that the creditor is receiving money on condition that he waives the debtor’s debt (Mishneh Lamelech, Malveh 5:14).
Your question on kefel assumes there was theft, which is apparently not the case. The coffee shop willingly gave Reuven the food, and therefore Reuven did not steal. Rather, upon receiving the food, Reuven became obligated to pay for it, and he (purposely) did not fulfill this obligation. While it is an aveira not to pay a debt (see Tehillim 37:21), such a person does not incur kefel. One could argue that it was theft because had Shimon known Reuven’s plan (assuming the "eat and run" move was planned in advance), he would not have given the food. That is a fascinating outlook which has several related applications (see Pitchei Choshen, Halva’ah 2:(26) for one), to which we cannot do justice in this forum. On at least technical grounds, had Shimon read Reuven’s mind at the moment Reuven would have been stealing, i.e., when receiving/eating the food, Shimon likely would have forced him take the food and pay, rather than take the food back. In any case, kefel is predicated on beit din’s ruling, and since we have lost the uninterrupted chain of semicha from Moshe Rabbeinu, we now lack the authority to obligate penalty payments such as kefel (Bava Kama 84b).
If we view the food as stolen, then indeed the berachot were themselves an aveira (Bava Kama 94a). However, if we are correct, the food is permitted, and the fact that the situation will likely lead to do a future aveira (not paying) does not preclude a beracha (compare toposkim on Shulchan Aruch, Orach Chayim 196:1). Certainly, the food cannot become stolen retroactively.
Bemare Habazak - Rabbis Questions (652)
Rabbi Daniel Mann
202 - Returning Another Person’s Theft
203 - Doing Tevilat Keilim Before Giving Present
204 - Tefillin in Pre-Dawn Hours
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