The title of this essay is taken from a conversation I had with Maran Harav Yosef Dov Soloveitchik, זצ"ל. I asked him if it is permissible to visit a casino for only one visit and nothing beyond that. The Rav's reply was succinct: "It's a bad habit, don't do it." Similar sentiments are expressed by the Mishnah Brurah (076 Biur Halacha,ד"ה ונוהגים ), Aruch HaShulchan (Orach Chaim 076:9), Rav Moshe Feinstein (Igrot Moshe Orach Chaim 4:53), Rav Yehudah Amital (personal communication), Rav Aharon Lichtenstein (personal communication), Rav Herschel Schachter (in a shiur delivered at Yeshiva University), and Rav Mordechai Willig (at a shiur delivered at an NCSY convention). We will explore the basis for this attitude in the Gemara, Rishonim, and the Shulchan Aruch.
The central discussion of the halachic attitude toward gambling is found in Sanhedrin 42b- 52a. The Mishna there lists men who are פסולים לעדות, disqualified from serving as witnesses. Included in this list is aמשחק בקוביא , which may be translated as "dice player." The Gemara cites two differing opinions why a משחק בקוביא is פסול לעדות. Rami Bar Chama believes that one's winnings in dice playing are actually theft, because the losing party does not give his money to the winner willingly, as a purchaser would give money to a seller in a routine sale. Rami Bar Chama believes dice playing is a case of "Asmachta." אסמכתא refers to a situation in which one agrees to pay money if he fails to do something. An Asmachta agreement is generally considered invalid because of the lack of full intent גמירת דעת(); he accepted the penalty only because he was certain that he would fulfill his promise and that the penalty would not apply. Rashi explains that Rami Bar Chama believes that משחק בקוביא constitutes Asmachta, because the losing party only agreed to pay if he lost, because he was certain he would win due to his gambling skills. Hence, when he hands the money to the winner he does so entirely unwillingly (אינו נותן לו מדעתו).
Rav Sheishet disagrees with Rami Bar Chama and asserts that משחק בקוביא does not constitutes an Asmachta. Rav Sheishet believes that the Mishna disqualifies only a habitual משחק בקוביא because he is an individual who fails to be עוסק ביישובו של עולם, engaged in a constructive activity. The Rambam explains (Hilchot Gezeila V'Aveida 6:01) שאין ראוי לאדם שיעסוק כל ימיו אלא בדברי חכמה וישובו של עולם - that it's wrong for a person to spend his time doing something other than being engaged in learning or some other activity which contributes positively to society.
Rashi, his grandson Rabbeinu Tam, and his great- grandson, the Ri, debate why Rav Sheishet believes gambling does not constitute Asmachta. Rashi explains that when one plays dice he does not have any control over whether he will win or not. Hence, if one agrees to pay if he loses, he does so wholeheartedly, because he knows that it is very possible he will lose. A case of Asmachta would be where a person was certain he would fulfill his promise and not have to pay a penalty. An example of Asmachta is the case in the Mishna (Bava Batra 861a) in which one promises his creditor to pay him more money than he truly owes if he does not repay the loan by a certain date. He agrees to pay the extra money in case of default, because he is certain at the time he makes the condition, that he will be able to pay his creditors by the agreed upon date.
Rabbeinu Tam offers an entirely different explanation. He explains that if משחק בקוביא would be a unilateral agreement it would be Asmachta and therefore invalid. However, בקוביא משחק involves a bilateral agreement to pay in case he loses, because each party wants the other to pay in case he wins. Rabbeinu Tam believes that Asmachta invalidates an agreement only if the person making the condition has no possibility to profit from the deal, such as in the aforementioned case that appears in the Mishna in Bava Batra.
The Ri essentially agrees with Rashi's explanation of Rav Sheishet, and adds a number of points to provide a full account of what is considered Asmachta and what is not. He outlines three basic categories of conditional agreements. The first category is when one makes an agreement whose terms are reasonable (לא גזים) and one is fully in control of the situation (בידו). The conditional agreement does not constitute Asmachta and is valid. The classic example of this category is the Mishna in Bava Metzia (401a) in which a sharecropper agrees to compensate the owners of the field if he fails to work the field - אעביד אוביר ולא אם במיטבא אשלם. The payment is not a penalty, rather it constitutes appropriate compensation to the owner of the field for the lost opportunity to glean profit from his field. In addition, the choice of whether to work the field or not is entirely in the hands of the sharecropper.
The second category is when one makes an agreement which either includes a clause with an exaggerated penalty or the situation is only partially in control of the person agreeing to the penalty. If the sharecropper agreed to pay the owner of the field a very large sum if he does not work the field, the agreement is an Asmachta if the penalty is disproportionate to the loss of money suffered by the owner. We assume that the sharecropper did not truly expect to pay that great sum. Similarly, in the Mishna in Bava Batra the situation is an Asmachta because of the borrower's overconfidence that he will succeed in paying his creditor on time. Indeed, the circumstances are partially under his control, which gives the borrower the confidence (or overconfidence) to make such a penalty agreement. However, since the circumstances are not fully under his control, he does not properly gauge the risk factor and hence never truly intended to have to pay the penalty he agreed to.
משחק בקוביא falls into the third category of the Ri. Since the situation is totally random, one does not neglect to consider the possibility that he might lose, when he agrees to pay a certain sum in case he does lose. Hence, משחק בקוביא is not considered to be a Asmachta according to Rav Sheishet.
The Rema cites the theories of both the Ri and Rabbeinu Tam regarding why משחק בקוביא is not Asmachta (see Rema, Choshen Mishpat 702:31). Indeed, the Rema (Choshen Mishpat 073:3) does not forbid the practice to engage in occasional משחק בקוביא, because halacha accepts the opinion of Rav Sheishet as normative. Rav Yosef Karo (שם), however, rules in accordance with the view of Rami Bar Chama that משחק בקוביא constitutes a theft because the agreement of the loser to pay is an Asmachta.
Accordingly, Sephardic Jews should not play dice, even on an occasional basis, since for them the rulings of Rav Yosef Karo constitutes the halachic norm. However, even according to Rema, the "permission" to be involved with משחק בקוביא is limited to those games in which the winner is determined entirely randomly (Rema cites the three categories of the Ri as normative Jewish law). In order to be permitted to engage in a gambling activity, one would have to ascertain that the game does not run afoul of the Asmachta rule. This is no simple task, as the laws of Asmachta are not simple and the crucial distinctions between valid and invalid agreements are very subtle and difficult for many to grasp.
Moreover, the Rema (C.M. 702:31) cites as normative the comments of the aforementioned Tosafot, that משחק בקוביא would be permitted only if the money to be kept by the future winner is placed on a table owned by both parties (see Biur Hagra C.M. 702:73). This requirement is not fulfilled in most cases of gambling (also see Shulchan Aruch Orach Chaim 223:6).
Moreover, Rav Mordechai Willig (a prominent Rosh Yeshiva at Yeshiva University) ruled that almost all forms of gambling are forbidden. He included horse racing and football pools as forbidden activities due to the ruling of the Rambam (Gezeila V'Aveida 6:01). The Rambam states that gambling constitutes theft on a Rabbinic level - הבעלים אע"פ שברצון גוזל בחנם דרך שחוק והתול הרי זה לקח הואיל ולקח זה ממון - even though the loser agrees to pay the winner, it is theft because the winner has acquired the winnings through play. Only when one is given money in exchange for goods or services is the money considered to be acquired in an appropriate manner. Obtaining money because he won a game constitutes theft on a Rabbinic level because he has given the loser nothing in exchange for the money he received. Even though, technically speaking, this is not an act of theft, the Rambam believed that Chazal (our Rabbis) decreed that gambling proceeds are to be considered as theft.
An exception to this rule is a lottery conducted to raise funds for a charity. Rav Yosef Adler reports that Rav Yosef Dov Soloveitchik z"tl ruled that purchasing a lottery ticket does not constitute Asmachta if the purpose of the lottery is to raise money for a charity. This is because the rule of Asmachta does not apply to charity (Shulchan Aruch Yoreh Deah 852:01). The reason for this is simple. One would not reluctantly relinquish his money in case he loses, since we presume that one is not disturbed that his money will be given to charity. Common practice in the observant community appears to follow this ruling and to conduct lotteries and raffles to raise money for charity. Accordingly, New York State Governor George Pataki's decision that the New York State Lottery Commission emphasize the public benefits (such as supporting public education facilities) of the lottery rather than the benefit of winning the lottery, appears to be very much in harmony with Jewish Law.
The many authorities cited in the first paragraph condemn engaging even in "recreational gambling" for moral considerations, even beyond questions of theft. The Mishna Brura and Aruch HaShulchan strongly discourage playing cards on Chanukah. Rav Moshe Feinstein refers to card playing and bingo as דבר מכוער, despicable activities. Rav Aharon Lichtenstein commented to me that casinos and gambling halls are "symbols of decadence in society." Rav Yehuda Amital said to me אנשים מחפשים את המתח בחיים, "people are seeking inappropriate forms of excitement," which he felt is unhealthy. Rav Soloveitchik put it succinctly - "It is a bad habit."
The Torah exhorts us: קדושים תהיו - be holy! All these great Rabbis declare that engaging in gambling activity is incompatible with our mission to be holy people. This approach is also in harmony with the Rishonim quoted by Rabbi Eli Clark in the latest issue of The Journal of Halacha and Contemporary Society, who strongly condemned the practice of being involved in gambling activities.
We should add that it is highly unusual for the Aruch HaShulchan to strongly condemn a practice of the observant community. Accordingly it seems puzzling that the Aruch HaShulchan so strongly condemns the practice of many to gamble on Chanuka. A possible reason is that the Aruch HaShulchan was the Rabbi of a city (Novaradok, in pre-World War I Lithuania). Hence, he may have seen the devastating impact that gambling had on many families, and perhaps this is why he so strongly condemned gambling during Chanuka. In short, let us remember the words of the Chofetz Chaim and Rav Soloveitchik respectively, regarding gambling- השומר נפשו ירחק מזה and "it is a bad habit, don't do it."