@comeonnow Issue isn't that he has flaws told before in this story, issue is that he can't learn. Had gambling incident and now he is exact same situation. Anyone would be cautious for at least 3, maybe 5 times before going to same routine (if not change entirely).
With his experience (gangs, police, assassins and most likely even more) anyone would learn to save before going to unknown situation, regardless of laziness or anything similar. That is the real issue.