If I may get it clear, OP, the winning in this context here means one winning a game, and my opinion is this, if you have lost a lot of games to the casino in the past, you can not say you have won the casino irrespective of whichever casino you have played with. The casino would still be winning because they have won you enough, not until you recover all you have lost from their casino through games won, then you can say you have won them anything outside that is just a mere saying if you have lost a lot of games to the casino.

Aside from the fact that gambling is for fun, if we gamble and lose, it is money we are losing out on, so the possibility of winning games to recover all we have lost is minimal, and if we win, it is small except for those who are lucky to win big and maybe that big win could be a huge amount of money in jackpot and if it covers the whole money the gambler has spent in gambling, that is a good win for the gambler because he has recovered all his losses.