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I do not particularly know the halachot of gambling, however, I have heard that under certain circumstances playing fantasy football might be allowed, if you do not expect to win money. I do not know if this is a real opinion or just something I may remember incorrectly. Has anyone else heard this or heard something similar?

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    You mean aside from the giant-waste-of-time aspect of it?
    – Double AA
    Commented Aug 26, 2020 at 0:07
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    Everyone has things they enjoy, yes.
    – Dov
    Commented Aug 26, 2020 at 0:10
  • Indeed and they should pick the productive ones to engage in. It's just hard to imagine any posek taking the gambling question part of this question seriously given the glaring other issues at play.
    – Double AA
    Commented Aug 26, 2020 at 0:20
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    Well why would a posek ever answer any gambling question then, given that its a waste of time?
    – Dov
    Commented Aug 26, 2020 at 0:26
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    google.com/amp/s/www.koltorah.org/halachah/…
    – sam
    Commented Aug 26, 2020 at 1:04

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The main halachic issue with gambling is "ashmackta". Ashmachta means to rely on. The basic idea is that if I am gambling because I am relying on my edge and there is no way I can really lose - then if I give my money over to the winner it is without full intent and there are issues with the winner making a kinyan on the winnings.
So for example there is a difference between betting on who won the 1972 superbowl, and who will win the next superbowl. You would bet on '72 because you are sure you know, and if you lose its a mistake. Next year no matter how sure you are - you know things can possible turn out different than expected in sport. There are differences how sefardim and ashkenazim poseken in this matter, with ashkenazim allowing more gambling than sefardim. Rav Ovadia does not allow to buy a lotto ticket - but many sefardim in Israel do anyway. In short - your comment if you do not expect to win money should be changed to - as long as you know and accept you may lose your money.

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