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When a billionaire leaves their money to charity that just means they want to dictate 1,000s of people's labor even after they die. There is nothing good about this. The only possible good thing to do would be to give the money to democracy – to let the public decide what to do.
Why should Bill Gates, after he dies, decide what a hundred thousand people do for 40 hours a week? Why should he decide what is good for society? Why can't we decide for ourselves? Private charity is still a dictatorship over work. Obeying a capitalist after he dies is absurd.
I think you are severely overestimating democracy there.
I think the ones endorsing charity state are severely overestimating the thing that isn't democracy. When democracy fails, it most probably just means there's not enough of it around.
This is the kind of armchair reasoning that gives armchair reasoning a bad name
There's no good way to redistribute wealth, just varying shades of less bad ways. We have to reorganize society so that wealth is distributed equitably in the first place, which is, y'know, #socialism! 
It's stored man power. 95% after a certain amount should go back into the market through public works and infrastructure. The rest can go to inheritance. Monopoly doesn't work if someone inherits your last position on the table at the beginning of every game.
Where is this democracy, and how do I give it my earthly possessions when I'm done with this mortal existence?
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