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Makes perfect sense to me.
There are two ways of being happy: you must either diminish your wants or augment your means. - Benjamin Franklin
Peter Schiff is only playing the role of the financial adviser who does not make choices for his clients, but only informs them of the consequences of any course of action they take. No better way of coming face to face with an obnoxious principle than its rigorous hypothetical application and enforcement (borrowing loosely from Lincoln).
He's putting everything into a very factual, matter-of-fact perspective. If you want a big government, raising taxes on the rich might make you feel good, and give you the illusion that it's being paid for, but that's not the reality, and that alone is not going to pay for it. If you want to tax the rich symbolically, but still plan to finance the lion's share from infinitely expanding newly printed fiat debt currency, you are very quickly going to reach a point of no return, wherein NO tax, even if levied on everyone in massive amounts, will make any difference at all, and can only make things progressively worse. At that point there is no longer a choice of going off a cliff or not. We're going off the biggest cliff of all, the only question being which ledge we go over, and at what trajectory.