I once asked Rav Yosef Dov Soloveitchik if it is permissible to go to a casino for a single visit, and he succinctly replied: "It's a bad habit, don't do it!" Rav Mordechai Willig later encouraged me to publicize the Rav's statement. Similar sentiments are expressed by the Mishnah Berurah (670, Biur Halachah s.v. VeNohagim), the Aruch HaShulchan (Orach Chaim 670:9), Rav Moshe Feinstein (Teshuvot Igrot Moshe, Orach Chaim 4:35), Rav Yehudah Amital (in a personal discussion), Rav Aharon Lichtenstein (in a personal discussion), Rav Hershel Schachter (in a lecture delivered at Yeshiva University), and Rav Mordechai Willig (in a speech delivered at a National Conference of Synagogue Youth convention). Rav Zvi Sobolofsky recently urged Torah Academy of Bergen County to refrain from participating in fantasy football gambling. We will explore the basis for this negative attitude towards gambling in the Gemara, Rishonim, and Shulchan Aruch.
The main Talmudic discussion of gambling appears in Sanhedrin (24b-25a). The Mishnah lists different types of men who are disqualified from serving as witnesses, including a dice player (Mesacheik BeKubiya). The Gemara cites two potential explanations for disqualifying a dice player. Rami Bar Chama believes that one's winnings in dice playing constitute theft, because the losing party does not willingly relinquish his money to the winner. Rather, it is considered a situation of Asmachta, where someone accepts a disproportionately large financial responsibility under the assumption that he will never have to pay it. Rashi (s.v. Asmachta) explains that Rami Bar Hama considers gambling to be an Asmachta because each gambler agrees to pay if they lose, only due to the mistaken belief that he will certainly win. Hence, when he hands the money to the winner, he does so unwillingly.
The Gemara, however, records that Rav Sheishet does not view the losing gambler's payment as an Asmachta. According to Rav Sheishet, the Mishnah disqualifies only a gambler who has no other profession, because he fails to engage in any constructive activity (Eino Oseik BeYishuvo Shel Olam). The Rambam (Hilchot Gezeilah Va'Aveidah 6:11) explains that a person should involve himself in learning and other activities that contribute positively to society, whereas even permissible forms of gambling (such as gambling with a non-Jew) contain no socially redeeming value.
The Rambam (Hil. Gezeilah Va'aveidah 6:10-11) rules that gambling with a Jew constitutes theft on a rabbinical level. Regarding gambling with a non-Jew, while not defined as theft, the Rambam prohibits it because it is neglecting man’s responsibility to spend his time productively acquiring wisdom and developing the world. The Rambam's opinion is somewhat difficult, because he appears to contradict himself in Hilchot Eidut (10:4), where he implies that even gambling with a Jew involves no technical prohibition. His opinion also does not seem to fit in the Gemara cited above.
Rashi, Rabbeinu Tam, and the Ri debate why Rav Sheishet maintains that gambling does not constitute an Asmachta. Rashi (Sanhedrin 24b s.v. Kol Ki Hai Gavna) explains that when one plays dice, he does not have any control over whether he will win or lose, for rolling dice successfully does not depend on skill. Hence, if one agrees to pay in the event that he loses, he does so wholeheartedly, knowing that he might lose. On the other hand, situations of Asmachta arise when a person is certain that he will fulfill his promise and thus avoid paying the penalty.
For example, the Mishnah (Bava Batra 168a) discusses a person who promises his creditor that, as a penalty, he will pay more money than he owes if he does not repay his loan by a certain date.He agrees to pay the extra money only because he is certain that he will be able to pay the creditor by the due date.Therefore, if the borrower defaults, the penalty is an Asmachta, as he did not expect to actually pay the penalty.The gambler, on the other hand, understands that he might lose his money, so he consents to his loss, making the gambling payment a permissible transaction according to Rav Sheishet.
The Ri fundamentally agrees with Rashi's explanation of Rav Sheishet, but he outlines three basic categories of conditional agreements to provide a full account of the parameters of Asmachta. The first category is when one makes an agreement whose terms are reasonable (Lo Gazim), and one is fully in control of the situation (BeYado). This conditional agreement is valid and does not constitute an Asmachta. The classic example of this category is a sharecropper who agrees to compensate the owner of a field if he fails to work the field according to their agreement (Bava Metzia 104a). The payment is not a penalty; rather, it constitutes appropriate compensation to the owner of the field for the lost profits. In addition, the sharecropper himself chooses whether he will work the field.
The second category described by the Ri is accepting a debt without seriously believing that one will ever have to pay it, such as when one agrees to pay an exaggerated penalty should he fail to do something. For example, if a sharecropper agrees to pay the owner of the field an exorbitant sum as a penalty for failing to work the field, the agreement is an Asmachta, because the sharecropper undoubtedly never expected to pay such a great sum (Bava Metzia 104b). He consented to the financial penalty only inasmuch as he believed that he would work the field properly and never need to pay the fine. Accordingly, the penalty constitutes an Asmachta and is not Halachically binding.
The Ri considers playing dice to be a third category. Winning and losing are totally random, so the players recognize that they might lose, and consciously agree to pay the required sum. No one is under the false impression that his superior skills give him a better chance of winning. Since each competitor knows in advance that he may reasonably need to pay this sum, playing dice is not an Asmachta according to Rav Sheishet.
Rabbeinu Tam offers a different explanation. He suggests that playing dice would be an Asmachta if it were a unilateral agreement. Playing dice, however, involves a bilateral agreement. One agrees to pay when he loses games, only because he wants the ability to collect when he wins. Rabbeinu Tam believes that an Asmachta invalidates an agreement only if the person commits himself to pay without receiving any potential profit in return, such as in the aforementioned case concerning defaulting on a loan.
The Shulchan Aruch and Its Commentaries
The Rama (Choshen Mishpat 207:13) cites the theories of both the Ri and Rabbeinu Tam to explain why playing dice is not an Asmachta. Elsewhere, the Rama (Choshen Mishpat 370:3) does not forbid occasional gambling, as the Halachah accepts the opinion of Rav Sheishet. Rav Yosef Karo (op. cit.), however, rules, in accordance with the view of the Rambam, that dice playing constitutes theft on a rabbinical level, and the agreement between the two parties involved is an Asmachta.
Accordingly, Sephardic Jews may not even gamble occasionally, since for them the rulings of Rav Yosef Karo constitute the Halachic norm. Indeed, Rav Ovadia Yosef (Teshuvot Yabia Omer 7: H.M. 6) rules that a Sephardic Jew may not buy lottery tickets. Even the Rama limits the permissibility of gambling occasionally to those games in which the winner is determined entirely at random. In order to engage in such an activity, one must ascertain that the game does not constitute an Asmachta in any way. This task is far from simple, since crucial distinctions between valid and invalid agreements are very subtle. Rav Aharon Lichtenstein (cited in Daf Kesher 1:83-85) notes that sports betting pools, for example, appear to be prohibited even for Ashkenazic Jews. In that form of gambling, each participant believes that his superior understanding of sports will help him bet on the right teams, so he does not expect to pay for losing.
Moreover, the Rama (Choshen Mishpat 207:13) cites the opinion of Rabbeinu Tam, that gambling is permitted only when the prize money is placed on a table owned by both parties (see Bi'ur HaGera, C.M. 207:37). Most cases of gambling do not fulfill this requirement, as they usually take place in the home of a single player or in a casino.
Raffles and Lotteries
A possible exception to the Halachic problems with gambling is a lottery conducted to raise funds for a charity. Rav Yosef Adler reports that Rav Yosef Dov Soloveitchik indeed permitted purchasing a lottery ticket to raise money for a charity, because the rule of Asmachta does not apply to charitable contributions (Shulchan Aruch, Yoreh De'ah 258:10). Asmachta occurs only when someone does not intend to truly obligate himself, but the losers of a charity fundraiser feel comfortable relinquishing their money, knowing that it will be used for a positive purpose.
Rav Aharon Lichtenstein (cited in Daf Kesher 1:83-85) offers a different reason to permit lotteries and raffles, explaining that one who purchases a ticket buys a right to compete in the lottery. At the time of this purchase, the buyer consents fully to the sale, and cannot decide to undo it later. Revoking such a sale would be the equivalent of one who purchases a stock, and demands to abrogate the sale after a subsequent stock market crash. Since undoing the sale of a raffle ticket is so unusual, purchasing one would be permissible. For Sephardic Jews, it has already been noted that Rav Ovadia Yosef prohibits purchasing lottery and soccer pool tickets. Nonetheless, Rav Ovadia cites the Ben Ish Chai (Teshuvot Rav Pe'alim 2: H.M. 30) as permitting raffles in which the prize is an object, as the winner does not directly take the money of the other participants. Common practice in the observant community is to conduct raffles as fundraisers.
The Rivash (432) describes gambling as "disgusting, abominable, and repulsive," noting its terrible effect on society even according to those who do not technically define it as theft. Rav Ovadia Yosef (op. cit.) adds to the Rivash's comments: “Also, regarding the lottery, there are many people who buy many tickets, [spending] almost their entire salary, thinking that one number may win, and in the end… they lose all their money and property.”
Due to moral objections, the authorities cited at the beginning of this chapter similarly condemn engaging even in "recreational gambling," in addition to the potential problems of theft. In 1996, Rav Mordechai Willig instructed a convention of the National Conference of Synagogue Youth to refrain from all forms of gambling (including horse racing, football pools, and rotisserie leagues), due to the aforementioned rulings of the Rambam (Hilchot Gezeilah Va'aveidah 6:10-11). Rav Willig admitted that many Ashkenazic authorities disagree with the Rambam's claim that all gambling with a Jew is actual theft. However, no one would question the truth of the Rambam's statement that gambling, even when there is no theft involved, is a sheer waste of time, the antithesis of wisdom, and contributes nothing positive to the world. Rav Willig cited many of the catastrophic results of habitual gambling, repeatedly decrying gambling and its results as "Churbano Shel Olam" - destroying society.
Rav Hershel Schachter (in a lecture at Yeshiva University) even objected to lotteries commonly conducted at weddings to determine which guest will keep the table centerpiece, based on a similar law in the Shulchan Aruch (Orach Chaim 322:6). He explained that the activity prohibited by the Shulchan Aruch, casting lots to determine which child in a family will receive the biggest portion of food, reflects a general prohibition against activities that teach people the thrill of gambling.
The Mishnah Berurah and Aruch HaShulchan (cited at the beginning of the article) strongly discourage playing cards on Chanukah. Rav Moshe Feinstein refers to card playing and bingo as despicable activities ("Devarim Mecho'arim"). Rav Aharon Lichtenstein commented (to this author) that casinos and gambling halls are "symbols of decadence in society." Rav Yehuda Amital said, "People are seeking [unhealthy] forms of drama." Rav Soloveitchik put it succinctly, as mentioned earlier - "It is a bad habit; don't do it!"
The Torah (VaYikra 19:2) exhorts us: "Kedoshim Tihiyu" ("Be holy"). Many great rabbis have declared that gambling is incompatible with the Jewish people's goal of being a holy people. While it is highly unusual for the Aruch HaShulchan to strongly condemn a practice of the observant community, he does so regarding the practice of many Jews to gamble on Chanukah. Perhaps he reacted so harshly because he served as the rabbi of a city (Novaradok, in pre-World War I Lithuania), where he may have seen the devastating effects that gambling often has on individuals, their families, and society as a whole. In short, let us all, both Sephardic and Ashkenazic Jews, remember the words of the Mishnah Berurah regarding gambling, "HaShomer Nafsho Yirchak MiZeh" ("He who values his soul will stay away from it").
Ashkenazic and especially Sephardic Jews are well-advised to refrain from engaging in gambling including fantasy football. One’s quality of life will be dramatically upgraded by spending his non-working hours engaged in spiritually and psychologically enriching activities, and spurning morally corrosive pursuits such as gambling. Finally, the Halacha does not regard winnings from gambling as a legitimate acquisition. One who regrettably gambled and won some cash in any gambling activity including fantasy football, must consult with his Rav as to whether he is required to return the winnings to the original owner.
Rav David Bassous (“Jewish Law Meets Modern Challenges” 1:40) adds a very important point noting that according to Ramban’s definition of Holiness (in his commentary to VaYikra 19:2) “gambling definitely falls into the category of unseemly activities with which, we as as a holy nation, should have nothing to do.”
In conclusion, I should note that Rav Mendel Senderovic was distressed when I told him that it has emerged as common practice, even among highly Torah committed Yeshiva high school students, to wager money on fantasy football games.He advised me to make every effort to convince my Talmidim to refrain from this activity.
 See the crucial discussion in Tosafot to Ketubot 47b s.v. Shelo.
 Rav Ovadia adds that even Ashkenazic Jews should not purchase tickets in Israeli soccer pools ("Toto"), as these tickets support soccer games played on Shabbat. We have already noted that, according to Rav Aharon Lichtenstein, these pools may constitute an Asmachta, as their participants believe that their superior understanding of soccer enables them to bet correctly.