As you say, "Plenty of Have-nots". While we are taught that it is a system built by and for winners, we are conditioned to forget that on the very fundamental level, it is a Loser Production Machine. Nobody really gets out alive (corporations aren't people), so believing a trillionaire is going to "win" by having the most stuff is really wrong. He wins by creating more losers than anyone else. Bezos has a more visible loser workforce that supports robots in warehouses, but this year, Musk is busy buying the government's loser management system from a professional loser-advertiser-convict.
Most people in this system that are 'successful' become so when they figure out that most of us are already trained to be losers: they only have to borrow enough money from us to hire us at discounted rates, declare bankruptcy and not pay for the utilized labors. Getting a government bailout is also a nice bonus using the same philosophy. It all comes down to our agriculture: machines and oil producing cheap food to overproduce cheap, disposable people.