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This paper argues that far from advocating fear of violence as a continuous source of civic provocation Machiavelli’s ideal ruler employs an aesthetic approach to civic violence; one that actually harms few citizens and moderates their fear with admiration through carefully considered psychological imperatives similar to those articulated two hundred years later in theories of the sublime. Such violence as there was would occur half a decade at a time in between which the citizens and the patria would enjoy stability, wealth and honor. It had a proven Medici provenance, having been developed through Cosimo de Medici’s intuitive genius for governance and was maintained by Piero and Lorenzo the Magnificent. The insight was empirically confirmed by Niccolò’s observations of similarly intuitive political savants; namely Cesare Borgia and Julius II. It was not given a technical title by Machiavelli, who unhelpfully referred to it as crudeltà bene usate (cruelty well used) but we might call it “the politics of the sublime”. Despite its most dramatic (and consequentially disproportionate) evocation in the Prince, Machiavelli’s reliance on the political sublime waned throughout his literary career, until he rejected it in a stunning critique of Cosimo’s reign in the Florentine Histories.