Quote · Dwarkesh Podcast
Ada Palmer – Machiavelli is the most misunderstood thinker of all time
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How Florence bargained with Cesare Borgia for survival
At 7:08 · chapter starts 0:00
Ada Palmer describes Machiavelli's diplomatic strategy with Cesare Borgia — unconditional loyalty, betraying allies, whispering 'Florence is loyal' to buy time. The massacre at Senigallia and Borgia's terrifying charisma. [1] — Ada Palmer "Florence could not defeat Cesare Borgia — the math was simply impossible. Machiavelli's entire strategy was to pledge unconditional loyalty…" 11:20
With an average papal reign of 10 years, Italy faced near-constant political upheaval since each new pope, often elected by enemies of the prior pope, reversed prior policies.
Florence could not defeat Cesare Borgia — the math was simply impossible. Machiavelli's entire strategy was to pledge unconditional loyalty, betray centuries-old alliances, and whisper 'Florence is loyal' into the most terrifying conqueror's ear in Europe, buying nothing more than the promise of being conquered last.
Machiavelli's diplomatic strategy with Cesare Borgia was to pledge total loyalty and buy time, knowing Florence could not militarily resist — just hoping to be conquered last.
The Borgias did everything right. Cesare built an empire through brilliant strategy. Then he got food poisoning at the exact wrong moment, and it all collapsed. Machiavelli's conclusion: that's not a reason not to imitate them. Fortune controls half of all outcomes. You evaluate deeds on their most probable result, not on how fortune intervened.
Machiavelli argues that no matter how skillful a ruler is, half of what determines outcomes is always fortune — entirely outside anyone's control.
