I just saw the Tom Cruise movie "American Made" this last Saturday. I'm suspecting Private Pilot Stephen Paddock made his money the same way Tom Cruise did in that movie.
I'm beginning to suspect his gambling was just a front to launder money. I don't see the Casinos tolerating someone who is continuously winning money from them. "Losing" they will tolerate forever, but "Winning"? No. They will start looking at this guy with great scrutiny if he has been winning for 20 years.
I suspect he did make money. The key would be to spread the wealth. Vegas has 104 casinos. If he won $500K a year, that's about $400 a month from each casino. Nobody's going to look at him twice for that kind of money. His specialty was video poker, where (according to the brother in one of the interviews) the payout was 99.37% plus hotel comps. The guy might have been Rain Man with numbers - he spent three years as an IBM auditor, and they don't hire dummies.
I haven’t seen the movie, but it makes sense his gambling was a front for another method of making money.