brianm comments on Counterfactual Mugging - Less Wrong
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From my perspective now, I expect the reality to be the winning case 50% of the time because we are told this as part of the question: Omega is trustworthy and said it tossed a fair coin. In the possible futures where such an event could happen, 50% of the time my strategy would have paid off to a greater degree than it would lose the other 50% of the time. If omega did not toss a fair coin, then the situation is different, and my choice would be too.
There is no value in being such a person if they happen to lose, but that's like saying there's no value in being a person who avoids bets that lose on average by only posing the 1 in several million time they would have won the lottery. On average they'll come out ahead, just not in the specific situation that was described.