Even if he loses, he's realizing what it takes to be a winner. And he realized something important about himself. He never wants to leave things to luck. He always has a plan and will only step up if he's sure of winning. The chairman still gave him an opening though, if Kaiji just had realized that lot had to be somewhere.
Personally, a system is nice, but the thrill of winning by chance is what makes the most of your win.