Niccolò Machiavelli looks at us with an ironic smile. He escapes us, deceives us and at times even mocks us: "For some time now, I never say what I think, nor do I think what I say, and even if I tell the truth sometimes, I hide it among so many lies, that it's hard to find it again." 1 That ironic smile hides a tragic figure. Usually well hidden, it reveals itself in the moments of deepest desperation. "So if I sometimes laugh or sing,/", he wrote soon after being tortured and imprisoned, "I do it because I have just this one/ Way of giving vent to my bitter cry." 2 I want to uncover what lies at the heart of this tragedy using Machiavelli's own interpretative technique. Uncovering a complex, at times deceitful figure is a problem that Machiavelli himself faced repeatedly in his years as Florentine Secretary. Whether it was Cesare Borgia or Caterina Sforza, Machiavelli had to interpret the gestures and words of statesmen that were masters of deception. The strategy he developed to uncover these statesmen's intentions was based on the analysis of human passions, on uncovering the fundamental trait that defined a man's character. I apply Machiavelli's strategy of interpretation to Machiavelli himself. I do so by relying extensively on his letters and his comedies. Machiavelli would have envied the wide access that we have to the most private works of our subject of study. Had he had access to similarly private works by Cesare Borgia, his job as the Florentine envoy would have been much easier. Through this work of interpretation of human passions, I will uncover the irreconcilable disconnect which shapes Machiavelli's tragedy. On one hand, he relates to his objects of desire by entirely abandoning himself to them, regardless of how unachievable they are. On the other, to obtain these objects of desire his analytical mind develops strategies which take pride in their adherence to what he called the "effectual truth of the matter." 3 His incapacity to reconsider his objectives in light of the means at his disposal and his tendency to transfer all of himself into his objectives determined Machiavelli's successes and failures. He repeatedly failed when he had to set his own goals, or when he approached a problem with empathy. He succeeded when he was given precise and limited objectives and when he understood that he did not share the goals of those he was studying. The next section discusses how other scholars have struggled to understand the fundamental disconnect at the heart of Machiavelli's tragedy, focusing on the final exhortation of The Prince. The third section describes Machiavelli's interpretative strategy. The fourth section applies this strategy to his personal writings in order to understand what passions animated him, and then uses these passions to interpret some famous passages of The Prince. The fifth section looks at his political successes and failures and explains them in light of this fundamental disconnect between goals and means. The final section asks whether Machiavelli was aware of this fund...

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