I can't tell if Alan really doesn't understand the concept of playing with an advantage and related positive expected value (+Ev), or if he is once again playing (dumb) with us.
Playing with an advantage, the basis of advantage play does not guarantee a win (in the short term), whether results of the actual play or contest drawing.
In the context of regular play for instance, a card counter will experience some of his bigger losing sessions, when he has his bigger advantage (and bigger bets out). Playing with that advantage does NOT guarantee a win in the short term. Those losses are short-term losses, what is referred to as variance. We CANNOT control what occurs in the short-term and despite playing with an advantage will experience short-term losses (variance). But when you ride out the short-term swings and accumulate enough play to get to the ever so important long-term, the math takes over. You CANNOT experience losses long-term when playing with an advantage! The variance becomes insignificant.
Drawings and contest work the exact same way. To play on Mickey's example, if you have a 1 in 100 chance to win $10,000 in a drawing, that is expected value of $100. You may not win that drawing, so your return is zero. That is variance. You were +ev for that drawing but did not win (short-term), just like the card counter doesn't always win when the count is positive. BUT, enter 1000 of those drawings with a 1 in 100 chance of winning $10,000, and the player is going to win his share and come out on top and pretty close to where he should be. That is the long-term and the math guarantees it.
And therein lies the problem. Alan and Singer before him, either don't understand the math, or refuse to believe it. I suspect it is the later, and as long as that is the case all the explaining in the world will make no difference. Again and again with these guys, it is a case of people living in an alternative universe, believing what they want to believe instead of what is real.