Isn't the expected value of both envelopes, prior to picking either, 0.5 * X, where X is the sum of the envelopes' value?<p>So one way to argue this is a fallacious problem is that you can't take an unknown (the actual value of the envelope that you picked) and pretend it's a known. The value of the envelope you are holding, prior to opening it, is 0.5 * X. The value of the other envelope is also (0.5 * (.66 * X)) + (0.5 * (.33 * X)) == 0.5 * X.<p>This may be too ill-expressed -- but there's something wrong with treating the value of an unopened envelope as anything other than completely probabilistic.<p>Put differently, don't you have to say<p>0.5 chance I picked the bigger envelope (call that A). In which case, the other envelope is 1/2A. So if I switch, I lose 1/2A.<p>0.5 chance I picked the smaller envelope (A/2). So if I switch, I gain 1/2A.<p>Which means if I switch, half the time, I gain 1/2A and half the time I lose 1/2A, for an expected gain of 0 from switching.