Related to: Can Counterfactuals Be True?, Newcomb's Problem and Regret of Rationality.
Imagine that one day, Omega comes to you and says that it has just tossed a fair coin, and given that the coin came up tails, it decided to ask you to give it $100. Whatever you do in this situation, nothing else will happen differently in reality as a result. Naturally you don't want to give up your $100. But see, Omega tells you that if the coin came up heads instead of tails, it'd give you $10000, but only if you'd agree to give it $100 if the coin came up tails.
Omega can predict your decision in case it asked you to give it $100, even if that hasn't actually happened, it can compute the counterfactual truth. Omega is also known to be absolutely honest and trustworthy, no word-twisting, so the facts are really as it says, it really tossed a coin and really would've given you $10000.
From your current position, it seems absurd to give up your $100. Nothing good happens if you do that, the coin has already landed tails up, you'll never see the counterfactual $10000. But look at this situation from your point of view before Omega tossed the coin. There, you have two possible branches ahead of you, of equal probability. On one branch, you are asked to part with $100, and on the other branch, you are conditionally given $10000. If you decide to keep $100, the expected gain from this decision is $0: there is no exchange of money, you don't give Omega anything on the first branch, and as a result Omega doesn't give you anything on the second branch. If you decide to give $100 on the first branch, then Omega gives you $10000 on the second branch, so the expected gain from this decision is
-$100 * 0.5 + $10000 * 0.5 = $4950
So, this straightforward calculation tells that you ought to give up your $100. It looks like a good idea before the coin toss, but it starts to look like a bad idea after the coin came up tails. Had you known about the deal in advance, one possible course of action would be to set up a precommitment. You contract a third party, agreeing that you'll lose $1000 if you don't give $100 to Omega, in case it asks for that. In this case, you leave yourself no other choice.
But in this game, explicit precommitment is not an option: you didn't know about Omega's little game until the coin was already tossed and the outcome of the toss was given to you. The only thing that stands between Omega and your 100$ is your ritual of cognition. And so I ask you all: is the decision to give up $100 when you have no real benefit from it, only counterfactual benefit, an example of winning?
P.S. Let's assume that the coin is deterministic, that in the overwhelming measure of the MWI worlds it gives the same outcome. You don't care about a fraction that sees a different result, in all reality the result is that Omega won't even consider giving you $10000, it only asks for your $100. Also, the deal is unique, you won't see Omega ever again.
So, is it reasonable to pre-commit to giving the $100 in the counterfactual mugging game? (Pre-commitment is one solution to the Newcomb problem.) On first glance, it seems that a pre-commitment will work.
But now consider "counter-counterfactual mugging". In this game, Omega meets me and scans my brain. If it finds that I've pre-committed to handing over the $s in the counterfactual mugging game, then it empties my bank account. If I haven't pre-committed to doing anything in counterfactual mugging, then it rewards me with $1 million. Damn.
So what should I pre-commit to doing, if anything? Should I somehow try to assess my likelihood of meeting Omega (in some form or other) and guess what sort of parlour game it is likely to play with me, and for what stakes? Has anyone got any idea how to do that assessment, without unduly privileging the games that we happen to have thought of so far? This way madness lies I fear...
The interest with these Omega games is that we don't meet actual Omegas, but do meet each other, and the effects are sometimes rather similar. We do like the thought of friends who'll give us $1000 if we really need it (say in a once-in-a-lifetime emergency, with no likelihood of reciprocity) because they believe we'd do the same for them if they really needed it. We don't want to call that behaviour irrational. Isn't that the real point here?
Not exactly madness, but Pascal's wager. If you haven't seen any evidence of Omega existing by now, nor any theory behind how predictions such as his could be possible, and word of his parlour game preferences has not reached you, then chances are that he is so unlikely in this universe that he is in the same category as Pascal's wager.