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Answer: The gemara (Sanhedrin 24b) gives two reasons why a mesachek b’kubia (=mbk – gambler) is pasul l’eidut (unfit to be a witness): 1) Rami Bar Chama – Because of asmachta (the loser of a bet did not plan to lose/pay), a gambler is a thief; 2) Rav Sheshet – A mbk’s life is unproductive, making him untrustworthy. The gemara says the practical difference is if the gambler also has productive activity. According to most, Rav Sheshet considers a mbk’s obligation valid.
The Rambam (Eidut 10:4; Gezeila 6:10) and Shulchan Aruch (Choshen Mishpat 370:1-2) mix between the approaches – mbk violates (each time) Rabbinic-level thievery even though he is pasul l’eidut only if he is a full-time mbk. The losing party’s agreement to pay is insufficient because it is likely to not be whole-hearted (S’ma 370:3). The Rama (CM 370:2) rules that part-time mbk is permitted. Therefore, Rav Ovadia Yosef (Yabia Omer VII, CM 6), regarding buying lottery tickets, which he equates to mbk, forbids it for Sephardim and permits it for Ashkenazim. Other poskim (see Rav A. Shapira in Techumin V; Teshuvot V’hanhagot IV, 311) argue that the Shulchan Aruch would permit lotteries because one expects to lose, he receives a lottery ticket with value, the rival gamblers do not interact, and/or because the money is taken by the lottery authority, not any specific counterpart.
Bemare Habazak - Rabbis Questions (654)
Rabbi Daniel Mann
481 - Taking Medicine to Facilitate Mitzvot
482 - Challenge with Monetary Prize
483 - Women Doing Work on Chanuka
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The Shulchan Aruch (Yoreh Deah 258:10) rules that one who made a conditional obligation to tzedaka cannot exempt himself due to asmachta. Arguably, since your motivation is noble (funds for a shul), this might apply. However, that will not suffice here because the question is about intent that one’s money will end up by his counterpart, and the shul is just background.
There may be a way of dealing with the limitations of asmachta, by strengthening the agreement by doing an act of kinyan (like a chatan does at the wedding) and having it take effect mei’achshav (immediately) and/or doing it in front of a distinguished beit din, or writing that it was done in front of such a beit din (see Shulchan Aruch, CM 207:14-15). This would apparently make it permitted according to the Rama but not the Shulchan Aruch (Bemareh Habazak (new edition) VI:95). To avoid machloket, because the details are not simple, and to avoid halachic ploys to remove moral issues (see Aruch Hashulchan, CM 207:35), we should look for a natural way to remove the stain of mbk.
A likely claim is that no one’s intent is to make money, but to create motivation and/or to make things fun. This is reminiscent of the practice of many good Jews to play dreidel on Chanuka for money. On the other hand, some require modifications or allow it only on Chanuka (see opinions and a compromise in Nitei Gavriel, Chanuka, p. 307-308; see also Shulchan Aruch, Orach Chayim 322:6). Also, you are not talking about small coins. Without knowing the group, we would not preclude the possibility someone could start off with a nonchalant attitude but could end up competitive and resentful over such things.
Therefore, while you might not have a problem and/or might be able to use the beit din chashuv system, we recommend the following (or equivalent) "mehadrin" modification. The pot is given to someone who will use the money for the shul, a get-together, etc. At his discretion, he will use some of the money for a modest prize object (not money) for the winner (based on Yabia Omer ibid.).
Rabbis in Midrash
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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.
Ein Aya Various Universal Stages of the Geula Process
Rav Kook examines the various stages of redemption, explaining how (in addition to the obvious oft-mentioned stages of ingathering the exiles, reviving the Hebrew language, army, state etc.) the messianic dream of world prosperity, the State of Israel and world unity can and are realistically and logically gradually coming true.
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
Rav Kook explains why the world was originally divided into the various seemingly contradicting ideologies and cultures, in order to develop each one respectively. Swords or armies symbolize how each respective ideology defends themselves, as well as deters their opposing ideologies and cultures. On the other hand, the messianic era will be one of peace, and Rav Kook explains the transition to that stage, which mankind is already undergoing.
The Land of Israel LGBT'S IN ISRAEL
The question was asked, how can one make Aliyah with the LGBT parades?
Kuzari -Rabbi Ari Shvat Kuzari class 7 - Five Accumulative Proofs of G-d
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.
