Why does Machiavelli dedicated almost the entirety of the chapter to Cesare Borgia?
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Out of the trials and tribulations of Cesare Borgia Machiavelli constructs a rise-and-fall saga that is itself a profoundly moving piece of storytelling. Machiavelli, especially in his later works, seemed to prefer to be thought of as an historian, and here he shows off his predilection for spinning the messiness of history into the stuff of great fiction to. That said, Machiavelli does much to undercut and subvert his own tendency to draw larger meanings out of complex events.
For example, Machiavelli posits Borgia as a kind of latter-day mortal equivalent of the legends of history: Moses, Cyrus, Romulus, Theseus. Where those ancient figures exist shrouded in a haze, their exploits mythologized, Borgia is, for Machiavelli, a contemporary figure, and thus cannot hope to live up to these precedents.