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I don't have the impression that Taleb's thesis is anything like choosing between two known valued bills on the ground. Maybe it would be more like:

"if you were going to hunt for $20 bills on the sidewalk, which park would you go to? Central Park always does pretty well but if you were to play 'double or nothing' for tomorrow's find, you couldn't guarantee that you'd find a $20 bill there just because you found one there yesterday."

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