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During the summer of 1502, the young Republic of Florence appeared fated to die as quickly as it had been born. Only four years earlier, the citizens of the Italian city-state had installed a democratic government after decades of oligarchic rule, first by the Medici family and then by the mesmerizing Dominican friar Savonarola and his followers. Now it verged on destruction. Cesare Borgia, the pope’s illegitimate son and a commander in the papal army, had recently conquered central Italy in a brutal military campaign, and now he threatened to make Florence the next victim of his ambition. He issued an ultimatum saying he would reinstate the Medici rulers by force unless the Republic paid him a sum of tribute money that amounted to a quarter of its entire budget.

Faced with this crisis, Florence dispatched its most loyal and capable diplomat, Niccolò Machiavelli, to confront Borgia at his court in Urbino. During years of government service, Machiavelli had proved himself to be a shrewd negotiator as well as an unwavering defender of democracy, justice, and civic virtue. When his diplomatic reports began arriving from Borgia’s court, however, they must have shocked their readers in the government offices. Rather than explaining his efforts to save the republic from Borgia’s grasp, Machiavelli filled his correspondence with the most extravagant praise of Florence’s deadly enemy, whom he called "splendid and magnificent," adding "there is no great enterprise that does not seem small to him, and in his pursuit of glory and gains he never knows rest or fears danger or weariness." In the end, Borgia spared the city largely because he feared provoking the king of France, who was Florence’s ally. But it must have seemed to the Florentines that their sober envoy had been lost to the lure of power politics.

In fact, this tension pervaded Machiavelli’s life and writings. A tireless champion of popular rule and civic humanism seemed to share a body with a most ruthless "Machiavellian," who believed that the ends justify the means in politics even when the end in question is nothing more than personal ambition. To explain how these two people, the civic humanist and the ruthless power monger, could exist in one man is the challenge for all biographers of Machiavelli, most recently Ross King in his book Machiavelli: Philosopher of Power . The author of the bestselling Renaissance histories Brunelleschi’s Dome and Michelangelo and the Pope’s Ceiling , King tries, quite persuasively, to explain Machiavelli’s contradictions by looking at the epoch in which he lived. The Italian Renaissance was an age of contradictions, in which science and superstition, high art and squalor, Christian piety and extraordinary vice, lived side by side on the streets of the great Italian cities. King suggests that we should not expect to find inner coherence in a man who lived in such an incoherent age. "The key to some of [Machiavelli’s] ambiguities," he writes, "may lie in the nature of the man himself."

Machiavelli’s numerous undertakings¯diplomat, playwright, poet, historian, political theorist, farmer, military engineer, militia captain¯make him, like his friend Leonardo, a true Renaissance man. Yet, like Leonardo, who denounced the "beastly madness" of war while devising ingenious and deadly weapons, Machiavelli is awash in paradoxes and inconsistencies.

Machiavelli was born May 3, 1469, the year that saw Lorenzo de’ Medici, known as "the Magnificent," rise to power in Florence. Machiavelli grew up amid the wonders of the golden age of the Florentine Renaissance, a contemporary of the great Renaissance men Leonardo da Vinci and Michelangelo Buonarroti. While little evidence survives of his youth, he seems to have received a thorough humanistic education in Latin, mathematics, and poetry, as well as some training in engineering and agriculture. The democratic revolution occurred when Machiavelli was twenty-nine, and the city’s previous officeholders were quickly replaced with supporters of the new republic. Amid this house-cleaning, Machiavelli was elected to the important post of second chancellor.

In theory, the second chancellor ran the government bureau that prepared official reports and correspondence about domestic affairs. In reality, however, Machiavelli was used as a foreign envoy almost immediately. For more than a decade, he diligently served the republic both as a high-level bureaucrat in domestic issues and as a diplomat charged with the government’s most important negotiations. Among other foreign assignments, he headed delegations to the king of France, the Holy Roman Emperor, and the Holy See. He also worked with Leonardo on a stunning although uncompleted project to divert the course of the Arno River as an act of war against the city of Pisa.

Yet Machiavelli’s good fortune did not last. In 1512 the combined forces of Spain and the papacy overthrew the republic, and the Medici family regained power. The new leaders arrested and tortured Machiavelli for his leadership during the republic and his alleged participation in a plot to restore the democratic regime. Although he was soon pardoned, he was never again allowed to occupy high office, much to his displeasure. He channeled his frustration into improvements on his small farm outside the city, and into literature.

During the next few years, Machiavelli composed a small library of diverse works that included not only his infamous handbook, The Prince , but also Discourses on Livy (meditations on the writings of the ancient Roman historian), Art of War , History of Florence , and a number of bawdy comic plays, the most famous of which, The Mandrake , is considered a classic of Italian theater. The contradiction in Machiavelli’s political career, between his ceaseless work for the republic and his admiration of Cesare Borgia, was now carried over into his writing. His Discourses offered a sustained defense of the thesis that "governments by people are better than governments by princes" and "the good citizen ought to forget private injuries for the love of his country," whereas The Prince carefully instructed tyrants how to gain and consolidate power, even against the public will, by ensuring that their "cruel deeds are committed well" and they are "capable of entering upon the path of wrongdoing."

By the 1520s, Machiavelli had sufficiently ingratiated himself to the Medicis that he was offered a place on a diplomatic legation to Rome. But no sooner had he taken up the post than the government at home was overthrown, the republic was restored, and Machiavelli found himself in trouble with his old democratic allies for accepting employment from the enemy. The man who argued in The Prince that a stern and willful ruler could dominate "fortune" was twice undone by chance, first when the Medicis came to power and again when they lost it. He soon fell ill and died June 21, 1527, but not before exchanging deathbed jokes with his friends about whether he was headed for heaven or hell.

King interprets the contradictions in Machiavelli’s writings as an expression of deeper contradictions in his mind and character, which should be understood in their historical context. This is a useful corrective. Today Machiavelli is too often read as if he were a contemporary professor of political science struggling to produce a coherent theory of democracy, or citizenship, or justice, or some such thing. King is right to note that an ambitious, successful Renaissance statesman like Machiavelli would be unlikely to measure himself by the academic values of systematic coherence and plodding argumentation. So it is foolish to begin by looking for these qualities in his work.

Yet King’s reading is not wholly convincing. While it’s true that Machiavelli was not an academic type, his works reveal an exceptionally lucid and thorough mind. It is impossible to believe King’s suggestion that Machiavelli flitted back and forth between these two radical extremes. In his Discourses , after reviewing policies like Borgia’s, he wrote "these are extremely cruel methods and inimical to every way of life, not only Christian but human, and every man should avoid them and prefer to live as a private citizen rather than as a king with so much damage to other men." Yet in The Prince , he cheerfully described Borgia’s murders, frauds, and hypocrisy, only pausing to comment, "having reviewed all the actions of the Duke, then, I would not wish to criticize him; rather, he seems to me worthy to be held up as a model." Some explanation is required here beyond the observation that Machiavelli was complex man living in a complex age.

Perhaps the most plausible interpretation of Machiavelli’s contradictions, one that has circulated since his own time, is that the Discourses present his true opinions on politics while The Prince is a satire intended to expose the tyrant’s secrets. It condemns his anti-democratic enemies by accepting their premises and then pushing them to their horrible but logical conclusion, much as Jonathan Swift’s "Modest Proposal" refuted the economic theory of its time by showing that, on these principles, the Irish should solve their financial crisis by eating the children of the poor. This is how Jean-Jacques Rousseau interpreted Machiavelli, saying, "While pretending to teach lessons to kings, he taught great lessons to peoples. Machiavelli’s Prince is the book of republicans."

Yet this view also has its shortcomings. None of Machiavelli’s surviving private letters indicate that he or his friends thought The Prince was a satire. Furthermore, the hero of the work is Cesare Borgia, and it seems that Machiavelli really did admire him and his unspeakable methods. His diplomatic reports about his meetings with Borgia, which certainly were not intended satirically, were even more fawning than The Prince . Indeed, soon after meeting Borgia for the first time, Machiavelli wrote a breathless essay, the title of which ran in part, "Description of the Methods Adopted by the Duke Valentino When Murdering Vitellozo Vitelli." The most famous picture of Machiavelli is Santi di Tito’s half-length portrait hanging in the Palazzo Vecchio in Florence. The subject’s expression is alert, knowing, almost smiling, and completely inscrutable.

Matthew Simpson teaches philosophy at Luther College. His most recent book is Rousseau: A Guide for the Perplexed .

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