game with a not too obvious solution

[Tailgunner]

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1) A kind man tells you that he has two envelopes each with money in them. He says that you can choose either envelope, open it, and keep the money in that envelope, or trade the contents of the opened envelope for the unopened one. Is there any strategy that has a higher expectation than randomly choosing, opening, and not trading?

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I'll pick what's behind pipe number one.

*thud*

::takes both envelopes::


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2) A millionaire is funding a game between you and another person. The other person is given 1000 one dollar bills and two identical envelopes. He is instructed to put any integral dollar amount up to $333 in the first envelope and put exactly twice that amount into the second envelope. He shuffles the envelopes and presents them to you. As in 1) you get to choose one envelope, open it, and then decide whether to trade for the unopened envelope. If you end up with the envelope containing less money, he gets $100. If you end up with the envelope containing more $, he gets nothing. What is a good strategy for you? What is a good strategy for him? What is his worst strategy?


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I'd pick the fatter envelope every time.