When Reason Became Unreasonable. Week 31: Machievelli's The Prince and Rousseau's The Social Contract

This week on Crack the Book marks a jarring shift in tone — and in time. After months steeped in medieval imagination, we start there with  Niccolò Machiavelli and end firmly in the Enlightenment with Jean-Jacques Rousseau. Their works, The Prince (1513) and The Social Contract (1762), straddle that uneasy moment when faith and hierarchy gave way to “rational” thinking. And wow, does it sound different. I didn’t realize how accustomed my ear had become to the older world until now.

First up, The Prince. I had only known it practically caricatured as a manual for ruthless rulers. Instead, I found that Machiavelli offers sharp, almost Aristotelian observations on how power works. Writing amid the chaos of Renaissance Italy — with popes, princes, and mercenaries vying for control — he tries to help leaders (well, Lorenzo di Medici) survive reality, not reinvent it. His advice is startlingly pragmatic: if you must be cruel, do it swiftly; keep the people’s goodwill by leaving their money and families alone; and above all, don’t be hated. Virtue matters less than the appearance of virtue — but even so, he respects human nature enough to work with it rather than against it. For someone with such a bad reputation, he’s refreshingly honest.

Before we move to Rousseau, I spend some time reviewing the Enlightenment: what it was, when it was, and how it changed thinking and therefore every other thing in the world! I think it’s a necessary bridge between these two time periods and books.

On to Rousseau. Two centuries and one worldview later, The Social Contract begins not with observation but with imagination: “Man is born free, and everywhere he is in chains.” Rousseau builds an elaborate theory of how people ought to behave, then blames reality when they don’t. His faith in reason and “natural goodness” feels detached from the messiness of human life that Machiavelli understood so well. And by the time he turns his ire on the Church in his final pages, the tone borders on bitter — foreshadowing the excesses of the French Revolution.

After this week, I find myself mourning the grounded wisdom of the Middle Ages. Machiavelli may be cynical, but at least he’s real. Rousseau feels like a man disappointed that humanity refuses to fit his theory.

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