This work offers a set of extended interpretations of Madison’s argument in Federalist X of 1787, using ideas from social choice theory and from the work of Douglass North, Mancur Olson, and William Riker. Its focus is not on rational choice theory itself, but on the use of this theory as a heuristic device to better understand democratic institutions. The treatment adapts a formal model of elections to consider rapid constitutional change at periods when societies face quandaries. The topics explored in the book include Britain’s reorganization of its fiscal system in the eighteenth century to prosecute its wars with France; the Colonies’ decision to declare independence in 1776; Madison’s argument about the ‘probability of fit choice’ during the Ratification period of 1787-88; the argument between Hamilton and Jefferson in 1798-1800 over the long run organization of the US economy and the election of Lincoln in 1860.