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I don't think this is how the world works. I rather think of betting against unknown future events as betting against unknown future events. You can't decide if it was a mistake based on the outcome, but only based on the available information when the decision was made.

Say he played a roulette, he was allowed to bet on black or red, both 50-50 chance, but the black paid more. He betted on black always, and got crazy rich. I'd say it was the right decision, even in the cases when red was the outcome. I don't even understand why would one think otherwise, and say that it was a mistake?



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