While democracy is derided for a variety of reasons in Plato’s thought, his most damning critique of that regime type does not involve an observation about democracy qua democracy, but of the transition that it so easily engenders: the decline to tyranny. Regimes are composed of individuals and groups, though, and Plato is anxious to ascribe culpability for the degradation. Two actors are the primary focus of his analysis — the political leaders and the demos. At times he emphasizes the puissance of the demos, but in other passages he suggests it is the leaders who are most authoritative. This paper discusses these apparently contradictory passages, and works towards a reconciliation. It argues that neither is assigned sole culpability, as both work in complex synrgy, and that the underlying cause of the decline—and the motivator behind both actors — is not simply freedom, but greed for material wealth.