The Jewish Eye
Is It Permissible to Play Dreidel For Money?
It is forbidden to be a "Misachek BiKubiya", one who plays an ancient game for money. There are two problems with this activity. First because when you win money it can be considered stealing from the one who lost. Second you are not involved in "Yishuv HaOlam", bettering the world, only wasting your time. The second problem we can dismiss right away because it only applies to those who do this daily instead of working and not occasionally as a means of relaxation.
Rav Yisroel Dovid Harfenes in his sefer on Chanukah, Mikadesh Yisroel Siman 3 discusses the various issues. With regard to "Gezel", stealing, the Halacha is "Asmachta Lo Kanya." If a person enters a bet because he is sure he will win, he never had any intention of giving you his money. Therefore if he loses and you take his money you are a thief! However, says the Mekadeish Yisroel, in games that he outcome is purely dependent on chance and does not involve any skill, when you agree to play you know can lose and therefore agree to pay the money. (The Mogen Avrohom says that even in this case while this is not Gezel it is Srach Gezel a hint of Gezel).
There still can be a problem of stealing though. When you lose the game you don't really want to pay. Since a "kinyan", legal transaction was not made, you are not obligated to pay. If you pay out of embarrassment then the money the winner receives is considered stolen money. On the other hand according to the Rema since the winner is not taking the money from you, rather he taking it off the table that all players placed it on before the game it may be permissible. There is also the issue of paying up to keep your word but that may not apply here since you didn't specify an amount you are giving.
This is a complicated Choshen Mishpat Sheila. We only write this to help stretch the mind and show how careful one must be in every monay transfer.
The Chochmas Adam dismisses this question and says that we play dreidel not to earn money but rather to be Mikayem a minhag Yisroel and therefore the whole question is not relevant.
Disclaimer: We try to convey the Tshuva to the best of our ability. We admit that our understanding may not be accurate. Please also understand that this Tshuva may not be the final word on this topic. One should consult a Rav before drawing any conclusions.
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