> If Ballmer is choosing his secret number uniformly at random, then the expected value of the game is [that you win $0.20]. But, as Ballmer points out in the linked video, if he knows you’re going to do a plain old binary search, then he certainly won’t ever choose 50 as his secret number. In fact, he has no reason to choose 25 or 75 either. Or 12, 13, 37, 38, 62, 63, 87, or 88. If Ballmer avoids those eleven numbers, and chooses uniformly at random from among the rest, that alone is enough to lower the expected value of the game from [$0.20] to about [−$0.0045].

So I think Ballmer was being perfectly honest in what he said: he does know a strategy that makes the expected value of binary search counterintuitively negative, and that strategy is (as he says explicitly) to avoid the first few numbers that you're going to guess. No further speculation about errors or deception on his part is needed.