If “the rich” actually had to work for thier money, they might get more sympathy. As it stands, the vast majority of the income earned by “the rich” is passive income which came into existence as a result of the work done by the working class. It is this value — created by the workers, not the rich — that “the rich” skim from.
Middlemen are parasites, not creators of value, and not producers. They lobby to create laws that force people to use their services and pay high fees to do so. CEOs (other than the founder-type CEOs who deserve respect) are usually “successful” because they are in the right place at the right time, and have the right connections. More often than not, they are the ones who cut jobs, lowering wages for workers…and then they have the audacity to complain that the tax base “needs to be broadened,” after they’ve impoverished the “47% who don’t pay taxes.”
In your analogy of people going out to dinner, if the richest diner got his money as a result of the work done by the other 19, then you’d better believe that the 19 will expect the one to pick up the tab for dinner.