I don’t know about him being “lucky”, quite the opposite. Everything that could go wrong, went wrong. Ironically the one thing he kept getting right, and the thing you’ve been trained to assume would go wrong after so many similar scenes in different movies, is that he would lose the bets he made, but he actually won them. What made the movie so deliciously sardonic, is that his crazy and irresponsible acts of placing crazy bets with every penny he had, was the thing he actually got *right*, but despite winning, everything else went wrong.