Here's a related point: Omega will never put the money in the box. Smith act like a one-boxer. Omega predicts that Smith will one-box. So the million is put in the opaque box. Now Omega reasons as follows: "Wait though. Even if Smith is a one-boxer, now that I've fixed what will be in the boxes, Smith is better off two-boxing. Smith is smart enough to realise that two-boxing is dominant, once I can't causally affect the contents of the boxes." So Omega doesn't put the money in the box.
By that logic, you can never win in Kavka's toxin/Parfit's hitchhiker scenario.
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Signals by Brian Skyrms is a great book in this area. It shows how signalling can evolve in even quite simple set-ups.