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thomblake comments on Counterfactual Mugging - Less Wrong
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There are various intuition pumps to explain the answer.
The simplest is to imagine that a moment from now, Omega walks up to you and says "I'm sorry, I would have given you $10000, except I simulated what would happen if I asked you for $100 and you refused". In that case, you would certainly wish you had been the sort of person to give up the $100.
Which means that right now, with both scenarios equally probable, you should want to be the sort of person who will give up the $100, since if you are that sort of person, there's half a chance you'll get $10000.
If you want to be the sort of person who'll do X given Y, then when Y turns up, you'd better bloody well do X.
I liked this position -- insightful, so I'm definitely upvoting.
But I'm not altogether convinced it's a completely compelling argument. With the amounts reversed, Omega could have walked up to you and said "I would have given you $100 except if I asked you for $10.000 you would have refused." You'd then certainly wish to have been the sort of person to counterfactually have given up the $10000, because in the real world it'd mean you'd get $100, even though you'd certainly REJECT that bet if you had a choice for it in advance.
Not necessarily; it depends on relative frequency. If Omega has a 10^-9 chance of asking me for $10000 and otherwise will simulate my response to judge whether to give me $100, and if I know that (perhaps Omega earlier warned me of this), I would want to be the type of person who gives the money.