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The Ruthless Ruler Behind Machiavelli’s The Prince

TL;DR

  • Machiavelli's first-person slip: In The Prince, Machiavelli accidentally wrote 'he told me' when describing Cesare Borgia's fall, revealing his personal proximity and emotional investment in the conqueror.

  • Borgia's supernatural charisma: Contemporary accounts describe Borgia as so persuasive that observers believed he must be the Antichrist or an incarnation of the angel of death, and Machiavelli was under his spell.

  • Florence's survival strategy: Machiavelli advised his republic to betray allies and abjectly serve Borgia, buying time like Odysseus's guest hoping to be 'eaten last' by the cyclops Polyphemus.

  • The Sinigaglia massacre: Borgia publicly forgave conspirators, renewed sacred vows in a cathedral, then slaughtered them at a banquet, a violation so heinous Dante would say a devil now inhabits his body.

  • Fortune over virtue: Machiavelli argues Borgia did everything right; his kingdom fell only because he and his father fell ill simultaneously, proving outcomes are half fortune, half skill.

  • Evaluating probability, not results: Machiavelli insists we judge leaders by what was most likely to succeed before fortune intervened, not by the final outcome.

The Breakdown

Machiavelli was so captivated by Cesare Borgia's terrifying charisma that he broke his own authorial voice, slipping into first-person just to defend the man who nearly conquered Florence.

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