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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 (657)
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.).

P'ninat Mishpat P'ninat Mishpat: Realtor’s Fee on Large Commercial Building – part I
(based on ruling 85031 of the Eretz Hemdah-Gazit Rabbinical Courts)
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Shoftim TESHUVA IN COURT OF LAW?
Parshat Shoftim-Chodesh Elul
Why does parshat Shoftim always come out during Elul? This innovative and central explanation is an eye-opener regarding many aspects of Judaism.

The Month of Elul TESHUVA IS THE ANSWER
The month of Elul serves as a vital time for self-reflection and personal accountability to prepare for true repentance.

P'ninat Mishpat P'ninat Mishpat: Realtor’s Fee on Large Commercial Building – part I
(based on ruling 85031 of the Eretz Hemdah-Gazit Rabbinical Courts)
(based on ruling 85031 of the Eretz Hemdah-Gazit Rabbinical Courts)

P'ninat Mishpat Complaints about Contractor’s Work – part II
(based on ruling 83037.1 of the Eretz Hemdah-Gazit Rabbinical Courts)
(based on ruling 83037.1 of the Eretz Hemdah-Gazit Rabbinical Courts)

Chemdat Yamim Moreshet Shaul: The Goal of an Agricultural Yeshiva – part I
Based on Siach Shaul, Pirkei Machshava V’Hadracha p. 263 (address at the laying of the cornerstone of the Yeshiva Chakla’it in Kfar Haroeh)
Based on Siach Shaul, Pirkei Machshava V’Hadracha p. 263 (address at the laying of the cornerstone of the Yeshiva Chakla’it in Kfar Haroeh)

Chemdat Yamim The Goal of an Agricultural Yeshiva – part II
Based on Siach Shaul, Pirkei Machshava V’Hadracha p. 263 (address at the cornerstone laying for the Yeshiva Chakla’it in Kfar Haroeh – 1938)
Based on Siach Shaul, Pirkei Machshava V’Hadracha p. 263 (address at the cornerstone laying for the Yeshiva Chakla’it in Kfar Haroeh – 1938)

Re'e NEVER EXTREME EXCEPT ISRAEL
Parshat Re'eh
Judaism is against extremism, so how can we understand the seemingly extreme statements found in our sages in favor of living in the Land of Israel and against living in Chutz laAretz? The article deals with the seeming contradiction between the strength of Free-Will and the strength of being influenced by our surroundings.

Ekev DANCE FOR ISRAEL- FOR YOUR BENEFIT
Parshat Eikev
Description: The 7 Haftarot we read after Tisha B'Av ("Shiva D'Nichemta") surely get us excited that they're coming TRUE, and awaken us to yearn, dance & join the return to Zion! The short article also deals with the problems and solutions facing the American Jewish community as discussed at a recent panel, as well as the question why Jews come from America to Israel to help when we face problems, but Israelis don't come to aid Jews in America when they face anti-Semitism.

P'ninat Mishpat P'ninat Mishpat: Complaints about Contractor’s Work – part II
(based on ruling 83037.1 of the Eretz Hemdah-Gazit Rabbinical Courts)
(based on ruling 83037.1 of the Eretz Hemdah-Gazit Rabbinical Courts)

Chemdat Yamim Moreshet Shaul: Twin Foundations
Based on Siach Shaul, Pirkei Machshava V’Hadracha p. 690
Based on Siach Shaul, Pirkei Machshava V’Hadracha p. 690








