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You can actually beat 50% in the envelope game

Asked at Jane Street

Two envelopes hold amounts aa and 2a2a for some unknown positive aa; you know nothing about aa. You pick one at random and open it to see XX. You may keep it or switch to the other.

Blindly switching (or blindly keeping) obviously gives the larger envelope with probability exactly 12\tfrac12. But consider this strategy: before playing, draw a random threshold TT from a distribution that is positive everywhere on (0,)(0, \infty) (say an exponential). After opening, switch if X<TX < T and keep if XTX \ge T.

Show that this strategy gives you the larger envelope with probability strictly greater than 12\tfrac12.

Show a hint

The two amounts are a<2aa < 2a. Consider where your random threshold TT falls relative to them: below both, above both, or between. What happens in each case?

Your answer

This one is open-ended. Work it through, then check your reasoning against the full solution.

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