[VarlosZ]

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Subquestion: Assuming I will pay his winnings out of my own pocket, is it morally reprehensible to not let my brother know that I'm not placing his bets in a casino?

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Yep. He's your brother; I have no idea what being your brother's bookie might do to that relationship. If you want to do this, he has to agree to it.

That said, not a bad idea if he's up for it and you're both totally reliable with money.