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If you have a chance, listen to this fantastic lecture (mp3) by Rabbi Michael Broyde. He discusses, for instance, a lawyer who does very boring, standard real-estate contracts, but his employer is a "men's entertainment company." Inherently it's basically permissible; in most circumstances, it's questionable to what degree you're really facilitating ...


There are 2 possible reasons given for the prohibition of gambling (both of which you mentioned in your question): a poor livelihood choice (yoshvei kranot) and theft due to a lack of a true legal contract / intention to give up the funds on the part of the loser (asmachta; i.e. everyone gambles because they think they will win and don't really have in mind ...

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