gregconen comments on Open Thread: February 2010 - Less Wrong
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The slight quantum chance that EY will 2-box causes the sum of EYs to lose, relative to a perfect 1-boxer, assuming Omega correctly predicts that chance and randomly fills boxes accordingly. The precise Everett branches where EY 2-boxes and where EY loses are generally different, but the higher the probability that he 1-boxes, the higher his expected value is.
And, also, we define winning as winning on average. A person can get lucky and win the lottery -- doesn't mean that person was rational to play the lottery.