This chapter focuses on Niccolò Machiavelli’s analysis of social strife, institutional change, and political leadership in the Florentine Histories, demonstrating that the work continues to affirm the radical, democratic republicanism that the author expressed in works such as the Discourses and even The
Prince. The chapter argues that the Florentine Histories continues to exhibit Machiavelli’s populist, democratic proclivities that favour empowerment of the common people over wealthy elites within republics. Moreover, it demonstrates that the Histories functions as an exercise in silent comparative constitutionalism; a tacit analysis through which Machiavelli demonstrates how, in ancient Rome, civic discord and political leadership produced admirable constitutional reforms that were conducive to civic virtue, but how, in medieval Florence, social conflict and elite prerogative generated deficient institutional innovations that facilitated civic corruption.