This surprises me. As much as I don't want to believe that people like this exist, but the other side of my brain is telling me it is somehow "achievable", only if you have enough connections and possesses something or someone that the an ordinary gambler doesn't have. Otherwise, everything seems close to impossible, especially when you said he's living decently and comfortable. This story is a direct opposite of the common story in gambling about people who've lost their wealth because they excessively used their money to bet.