I'm not attempting anything epic or mind-boggling here, EI.
All I'm saying with this comparison is that if we're going to make more successful people pay out more of their money simply because they're more successful in an attempt to "even the field" why not make students share their "wealth" when it comes to grades? Everyone is already assuming these days that rich people are lying, cheating bastards and it's wrong. Why don't we assume that all students with high grades are cheaters? It's quite simple really, that's not how we see them.
It's more of a joke if anything, this example. It's not meant to be a sound, logical example shown for reasons that include saving the economy and the rich. It's an example that works to me because in my mind, a lot of successful people worked for their keep and should be paid accordingly without being forced to pay more simply because they earned more than some bum who never complete high school and doesn't want to work a janitorial position because it's "below his standards".
A lot of people are lazy, a lot of people are driven. Not all successful people are successful through honest means obviously, but then again not all poor people are victims. Plenty of people are poor because they're underachievers, or they didn't take opportunities that were offered to them or simply because they want other people to take care of them.
What people are basically saying who support a scaled tax depending on income, is that there is a middle ground and that's where we should be. Poor people would pay nothing, and the rich would pay large amounts because "they don't need it" which is language that translates into "We don't want them to have it" or "a rich lifestyle is wrong".