Through an extended critical engagement with John P. McCormick's Machiavellian Democracy, this paper aims to shed light on Machiavelli's account of relations among the many and the few in the Discourses on Livy. While we agree with McCormick that Machiavelli should not be too quickly subsumed within the republican tradition, as interpreted by the “Cambridge School,” we reject the idea that Machiavelli's central thrust is prodemocratic. By focusing on the structure and logic of Machiavelli's arguments, we show that Machiavelli was critical of the capacities of ordinary citizens to govern themselves. As a result, Machiavelli emphasized and endorsed continuous elite intervention in the political life of the mixed regime, even as he paid due attention to the people's participation in a political regime with appropriate laws and institutions. Machiavelli's political theory, as embodied in the Discourses on Livy, challenges the transparency and equality that contemporary egalitarians and democrats embrace.