Plato has been read as a virulent opponent of democracy, a common interpretation that, among other things, either ignores or dismisses his perceptive account of the ways democracy can be a mistaken political culture. In Books 8-9 where he designs other cities that are less than his ideal city, Plato tries to show how the whole manner of living and esteeming of a ruling class pervert the preferences and decision-making of everyone living in the city. Attention to this account can reveal Plato not so much rejecting but contesting the democracy he designs-in-theory. In the city he models, freedom and equality are misdirected, its own political culture ultimately betrays itself. I argue that, for Plato, democracy’s failure is due largely though not exclusively to a remnant of oligarchy that remains within it —the underhanded and excessive pursuit of money— which undermine the freedom and equality that define its political culture.