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- Theft and Damage
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 (654)
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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Kuzari -Rabbi Ari Shvat Kuzari class 8- "Answering Questions on the Kuzari's Proof from Mass Revelation
Lessons
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Kuzari -Rabbi Ari Shvat Kuzari class 9 - "Seeing is Believing" (parag. 21-30)
These paragraphs elaborate on the theme that seeing and knowing is better than any attempt to prove logically, and begins explaining the difference between Israel and gentiles.

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Kuzari -Rabbi Ari Shvat Kuzari class 8- "Answering Questions on the Kuzari's Proof from Mass Revelation
How do we know that the "claim" of mass revelation to 2,000,000 witnesses at Mt. Sinai is really true? This important class answers all of the questions skeptics ask about this claim of the Kuzari.

Ein Aya Armies Still Necessary for Balance & the War Against Wars
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The Land of Israel LGBT'S IN ISRAEL
The question was asked, how can one make Aliyah with the LGBT parades?

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As a preparation for the Kuzari's classic proof of G-d from the mass-revelation at Sinai, we start here with 5 other directions to strengthen our belief which also contribute to what the Kuzari will present as well.

Ein Aya Muscle & Meaning: The Dual Nature of Gevurah (Physical Strength)
Is physical strength and fitness a necessity or an ideal? Although it if often totally overlooked among topics of Judaism, Rav Kook writes that it clearly is also a necessity to deter the many enemies of Israel, but even in Y'mot HaMashiach, in the Messianic era, to a certain extent, it's ideal continues even after our enemies will have been finished off.








