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Answer: The mishna (Shabbat 148b) allows using a lottery on Shabbat to give out food servings to household members, as long as it is not to give the "winners" bigger pieces than the "losers." The gemara (ibid. 149a) permits lotteries only within the household because others are assumed to care about their portion’s size, raising problems of measuring/weighing. The gemara continues that regarding different sized pieces, a lottery is forbidden even during the week because of kubiya (gambling). Some add Shabbat concerns of shitrei hedyodot (mundane documents) and that one might write (Sefer Hachayim [Kluger] 326:6). The Shulchan Aruch (Orach Chayim 322:6) codifies the gemara, mentioning the concerns of measuring and gambling.
We will not explain here why we assume that lotteries/raffles are not a problem of gambling (see our column, Vayeishev 5782). We note that the gemara’s case is not brought as an example of mesachek b’kubiya in Choshen Mishpat. Yet, it is still relevant here, because this kubiya-like behavior is considered a form of monetary deal making, which is itself a reason for a Shabbat prohibition (see Maharil, Shabbat 32; Rama, OC 338:5; Mishna Berura 322:22). We also will not deal with the issue of giving presents on Shabbat because of the prohibition of acquisitions (see Mishna Berura 323:1). This is quite solvable (see ibid. 306:33; Living the Halachic Process II, C-17).
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Can we claim that the prizes given out are not the type that are measured, thereby removing a major problem? The poskim (see Magen Avraham below) assume that the prohibition applies even to things that are not measured (see Avnei Yashfei III:42). Can we argue that youth groups are like families, where people do not make an issue of what they received? That claim is overly optimistic from practical and halachic perspectives. Even within the household, most Rishonim only permit a lottery of same-sized portions (see Beit Yosef, OC 322). It may also not apply to cases where the prize provider is giving his own property, in a way that he may do what he wants (Mishna Berura 322:22); this is usually not the case at youth groups.
The Magen Avraham (322:9) permits a lottery to determine who will get an aliya. His source is the lotteries held in the Beit Hamikdash on Shabbat and/or Yom Kippur. Most say this leniency requires a combination of both the fact that no object is being given out and that it is a matter of mitzva (Shvut Yaakov III:24; Kt’zot Hashulchan 146:32; Shevet Halevi IX:78). Some permit non-object lotteries even without a mitzva (Be’ur Halacha to 322:6). The Magen Avraham does not allow a lottery just on the basis of mitzva (e.g., as one can claim for religious youth groups). Whereas we find allowances for business-like activity for mitzva needs in auctioning off aliyot with the proceeds going to the shul or giving presents for mitzva purposes (see Magen Avraham 306:15), that is not the case for raffling off objects.
We are not prepared to declare as clearly forbidden something that is done in religious contexts and many rabbanim allow to occur (see also Shevet Halevi ibid. stopping short of outright forbidding it). However, we have failed to find a way to justify it. There are some alternatives. Contemporary poskim are known to disagree on whether one may give out raffle tickets on Shabbat and have a drawing after Shabbat (although it is unclear why the tickets are not muktzeh if it is forbidden to do the drawing on Shabbat). Raffling off mitzva honors would seem fine.
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