Dr_Manhattan comments on Firewalling the Optimal from the Rational - Less Wrong
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Not necessarily. Your model could have been quite reasonable, and yet something weird happened in the world. Sometimes, people win the lottery twice on the same day.
I think EY is pointing to the case of somebody winning the lottery twice in a lifetime, which people would think is incredibly weird, despite it being very normal - see http://www.amazon.com/Understanding-Probability-Chance-Rules-Everyday/dp/0521833299. I suspect that the "looks weird" due to having the wrong model is more common than "looks weird" due to being an outlier.