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I have only a guess that relates to the practice of keeping a stack of folded bills in a money clip.
It was customary to put the larger (better) bills on the inside so as not to reveal your true wealth



That might be true for rich skinflints. Poor richman-wannabes would put the largest bill they can on top and fill the rest with small bills in hopes that people will think they are more affluent than they really are. That would give a more logical meaning to "top dollar" as well. Ever hear of a "Michigan Bankroll"? It's a thick wad of nothing but ones. Tourism is big business in Michigan and if you work in the service industry, you are usually in possesion of a Michigan Bankroll, for a little bit anyway, until you get your bills paid...