Wisdom is the truest form of wealth, so my vote goes to Terry Davis.
As for the others: how about ranking them by burn rate rather than the sheer size of their bank balance?
I throw Katie Charm into the ring for #1, having blown a few millions' worth of bitcoin bucks quite rapidly.
I'd put DSP up there too, he "only" makes low six-figures but every penny of it goes into gacha games.
Brianna and Frank Wu are high rankers for all the stupid cars and vanity projects, but perhaps not as high as DSP, averaged over time.
Are there any "Internet Famous" people who are rich but on a downward spiral? Contrapoints maybe?
If CWC joined Cameo he would probably shoot really high up on the income level practically overnight. I know many of my friends would get 'zapped to the extreme' on their birthday if I could make it so.