But, that is kind of a false impression. If you have the money/credit line to join in the more expensive betting, then basically, you are paying for it.
So many of the services at the casino are "comped" (I think that is how you spell it) because the casino would rather you spent your money at the tables or slots, than on the drinks, food, etc. They don't want you to leave the tables, because you don't have the cash for another drink.
You are paying for it, because the casino wins. Isn't that the impression of the person who is spending such large amounts of money at the casino? Some days they win, some days they lose. Mostly they lose. The casino is the winner in the end.
The difference in high rolling is the amount of money and level of service. The fact that $100,000 or more can be gained by the casino leads to a high level of attention being paid to the gambler. This attention is generally (and I am generalizing) what high rollers crave. Perhaps Bennett did not need or crave that attention since he got plenty in the rest of his life's work.
But when you are being given that kind of attention you do not have control over the interpersonal dynamics, only your half of them. That can lead to problems. For example a CEO who surrounds himself with syncophants will ultimately fail because nobody is going to tell him when he makes bad decisions so he won't learn from his mistakes.
Similarly people who surround themselves with servants are going to have a harder time gaining feedback to increase their virtue. Everything they do is acceptable regardless of whether it is virtuous. And that's a situation that can strain the virtue of the even the most virtuous.
Bennett should simply not have put himself in that position.