Ballmer's argument is essentially about tail risk. Expected value is absolutely not a good way to make bets if you value survival, because you only get one shot. Same reason you wouldn't go all in every time you get a poker hand that's "expected" to win. Because you'll (very probably) be bankrupt in a few hands.
Sure the mean is +$0.07 or whatever, but the spread on that surely goes over the 0 line. So there may well be marginally more chance of winning than losing, on average, but you're only gonna get one outcome. So if the goal is to play to win, or else, then you probably shouldn't unless you like owing Ballmer money.
What would be more interesting is to monte carlo simulate this strategy and look at the win/loss distribution. Presumably the choice is then not so clear cut.
If you're allowed to play the game a few trillion times or so, then by all means bleed him dry :P