How Machiavelli Trolled Europe’s Princes

Machiavelli’s advice for rulers was ruthless and pragmatic—and he may have intended for it to secretly destroy them.

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In the winter of 1538, an Englishman living in Italy travelled to Florence. Cardinal Reginald Pole was a devout adherent of the Church of Rome at a time when the English Reformation threatened to tear the Church apart. He had fled into self-imposed exile from his native shores after opposing King Henry VIII’s divorce from Catherine of Aragon, and settled in Italy.

Along with his other business in Florence, Pole had a personal mission. About a decade before this journey, he’d had a conversation with Thomas Cromwell, a man of low origins who now served as the king’s most intimate counsellor. Cromwell had stopped at nothing—or so it seemed to Pole—to indulge Henry’s lusts and blasphemies. It was this ambitious adviser who, Pole believed, had masterminded the monarch’s divorce, put England in a state of war with the Church, had priests and noblemen murdered—and had always found some righteous pretext to color these deeds.

Contemplating the evils that had driven him from his homeland, Pole longed to get his hands on a book about statecraft that Cromwell had praised when they’d met. The book’s author was a citizen of Florence. He had died over 10 years previously, so Pole could not meet him in person. But if the cardinal could read that book, it might help him better understand Cromwell’s mind and Henry’s actions, and thereby make sense of what was happening to his poor England.

On acquiring a copy, Pole began to read with fascination, then with growing horror. “I had scarcely begun to read the book,” he later wrote, “when I recognized the finger of Satan, though it bore the name of a human author and was written in a discernibly human style.”

The Florentine’s text laid bare all the doctrines that seemed to guide Cromwell’s policies. Princes, it said, should build their states on fear rather than love. Since they live in a world teeming with lies and violence, they have no choice but to practise duplicity. Indeed, the prince who best knows how to deceive will be the most successful. In short, Pole declared, the book Cromwell so admired is full of “things that stink of Satan’s every wickedness.” Its author is clearly “an enemy of the human race.” The book that so appalled Cardinal Pole was the Prince, and the name of its author Niccolò Machiavelli.

Aghast and intrigued, Pole was determined to find out more about the man who could write such things. Machiavelli, it transpired, had at one time caused a good deal of trouble for Florence’s own princely family, the Medici. In 1512, a year before Machiavelli wrote his most notorious work, the new Medici government had ejected him from the civil-service posts he’d held for nearly 15 years, then imprisoned and tortured him on suspicion of plotting to overthrow the principality. These fragments of biography must have come up when Pole asked his Florentine hosts about their compatriot. For, he wrote, when he told them his thoughts about the book, they excused the author, “answering the charge with the same argument that Machiavelli himself had offered when they had confronted him.”

Machiavelli’s reply, the Florentines said, had been that not everything in the Prince expressed his own opinions. Rather, he’d written what he thought would please a prince, particularly the Medici prince to whom he dedicated the slender volume: Lorenzo di Piero de’ Medici, a young man with tyrannical leanings. But, Pole’s unnamed hosts continued, Machiavelli’s aim wasn’t just to flatter his way into favour: he had a more sinister purpose.

This wiliest of writers had no illusions about the utility of his cynical teachings. In fact, he was sure that any prince who put them into practice would soon arouse popular hatred and self-destruct. And this, said Pole’s Florentine friends, was precisely what Machiavelli wanted. His design “was to write for a tyrant those things that are pleasing to tyrants, bringing about in this way, if he could, the tyrant’s self-willed and swift downfall.” In other words, the book’s most shocking advice was ironic. Its author wore the mask of a helpful adviser, all the while knowing the folly of his own advice, hoping to ensnare rulers and drag them to their ruin.

This explanation made sense of something that had bothered Pole while reading the Prince. Though Machiavelli was clearly a man of uncommon intelligence, some of his maxims seemed to show, as the cardinal put it, a “crass stupidity.” It seemed obvious to Pole that a prince who wins power through fear won’t achieve security for himself or his state. The Prince claimed to put hard political facts ahead of moral ideals. But as a handbook on how to secure power, its advice was flagrantly unrealistic. Machiavelli’s self-proclaimed realism, his book’s main selling point, was a fraud. And Thomas Cromwell, Henry VIII, and England were among its first victims. Cromwell had taken the Prince at face value, Pole insisted, imbibing its devilish doctrines in the belief they were highest prudence—and in doing so had walked straight into Machiavelli’s trap. If the writer were alive, he’d be laughing at his handiwork. The results, though, were no laughing matter. England in 1539 was far along the road to perdition, and other Christian monarchs might soon go the way of Henry, should they or their counsellors fall under Machiavelli’s spell. “Mark this well, rulers,” Pole warned; beware of this two-faced writer. “For it is the aim of his doctrine to act like a drug that causes princes to go mad,” making them attack their own people with “the savagery of the lion and the wiles of the fox.”

Pole was the first of many readers to demonize Niccolò Machiavelli and associate his name with the unscrupulous practices of men like Thomas Cromwell. The Prince as political poison, its author as a cunning fox, Old Nick, Satan’s emissary, cold-blooded destroyer of kingdoms and of true religion: these images of Machiavelli and his writings soon came to play a big role in the propaganda wars stirred up by the Reformation. The conjurors of this demonic Machiavelli were mostly men of religion, both Catholic and Protestant. The enemies they branded as Machiavelli’s disciples challenged traditional relations between Church and state. Some were devout Christians like Cromwell who sought to weaken political ties with the Church of Rome. Others called for a new, more secular kind of politics.

Some of these sixteenth- and seventeenth-century challengers fought back by defending the Florentine against their opponents’ smear campaign. And in this way a very different Machiavelli—this one altogether human, and humane—joined his evil double on the political stage. His champions found their undevilish Machiavelli mainly in his Discourses and Florentine Histories, much longer books than the fast-paced Prince. This Machiavelli was a thorough- going republican, a “eulogist of democracy.” His aim was to defend the rule of law against corrupt popes and tyrants. And he sought to uphold high moral standards, not lower them to fit the gritty realities of political life. True, his morality came from ancient writers such as Livy, Plutarch and Xenophon rather than Christian Scriptures, and he loved to ridicule the empty moral platitudes of his day. But he never wanted to sever politics from morality. He simply wanted to put morality on firmer, purely human foundations.

But how could this image of a virtuous Machiavelli be squared with everything he says in the Prince? His defenders’ answer was that the Machiavelli of the Prince is a master ironist, a dissimulator who offers advice that he knows to be imprudent. On this point, though in nothing else, they agreed with Cardinal Pole. But while Pole thought that Machiavelli dissimulated so that he could poison princes’ minds and drive them mad, his admirers believed he did so only to unmask their deceits and their secret lusts for power. When he writes that Pope Alexander VI never did anything, or ever thought of anything, but how to deceive men, Machiavelli seems to praise the pontiff’s obsessive duplicity—but really exposes his pretensions of piety. When he describes how Cesare Borgia scapegoated his own governor, having him sliced in two pieces and laid out in the piazza at Cesena with a bloody knife close by, Machiavelli gives readers an unforgettable image of how far princes will go to hold on to power—showing that the writer’s true intention in the Prince was to expose the perversities of princely rule. His purpose was to warn people who live in free republics about the risks they face if they entrust their welfare to one man. If Machiavelli’s writing horrified priests and monarchists, this was because no one else had so daringly stripped away the veneer of moralism they used to hide their tricks.

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When I first started writing about Machiavelli, over a decade ago, I knew little about these early polemics. Like most present-day readers, I assumed that the Prince’s author was a pragmatist and a patriot. Recent scholarship told me, over and over, that he was devoted to the salvation of his city, Florence, and his country, Italy, at a time when they were being torn apart by war and civil war. If he sometimes excused violence and hypocrisy, he did so for good, patriotic ends.

But the more I read, the more I found myself questioning this picture. I began to notice that Machiavelli’s writings were extremely ambiguous. They seemed to speak in different voices at different times, saying very different things. In one breath he’d praise the ancient Romans for using two-faced means to create their vast empire. Then he’d say, almost by-the-by, that these policies sparked ferocious resistance and fuelled bitter rivalries inside Rome, rivalries that eventually drove the republic to its ruin. In the Prince, he seems to applaud men who break their oaths at will, caring little for good faith or justice. But he also says—in a passage most scholars pass over without comment—that victories are never secure without some respect, especially for justice. Turning to his Discourses, I’d seize on a tough-talking statement about ends justifying unjust means: surely this was the true Machiavelli speaking? But then, a few lines on, there’d be a dramatic example showing the exact opposite: that unjust means tend to ruin good ends, including the salvation of one’s country.

For every cynical Machiavellian argument I encountered, I’d come across two or three other arguments that clashed with it. The cynical arguments are louder, and more thrillingly unconventional. But the reasons Machiavelli gives for them are often illogical, or just feeble. At times it sounds like he’s parodying cheap rhetorical sleights of hand, the kind one often hears coming from the mouths of politicians and their spin-doctors. But he gives much more powerful reasons for actions we don’t normally think of as Machiavellian. Know your own limits. Don’t try to win every battle. Treat other people with respect so you can get them on your side and keep them there; observe justice with enemies as well as friends; always uphold the rule of law. These are a few of Machiavelli’s less notorious but more closely argued maxims.

Like Cardinal Pole—whose comments I hadn’t yet read—I soon began to doubt that Machiavelli believed every piece of his own advice. Several years after writing the Prince, he wrote to a close friend that for a long time I have not said what I believed, nor do I ever believe what I say. And if sometimes I do happen to tell the truth, I hide it among so many lies that it is hard to find. I sensed that the political wisdom he held to be truest wasn’t encapsulated in eye-catching maxims like ‘It’s better to be feared than loved.’ With statements like these, he seemed to want to get under his readers’ skin: to irritate them, tease them, make them think and think again about the examples he set before them. As I laboured to figure him out, I began to feel the way Machiavelli says he felt while reading a rather convoluted letter from his friend Francesco Vettori. Your letter, he wrote to Vettori, dismayed me: its organization, its countless lines of reasoning… entangled me in such a way that at first I was bewildered and confused. But then, as I became more familiar with it, the same thing happened to me as it did to the fox when he saw the lion in one of Aesop’s fables. The first time, he almost died of fright; the second, he stopped behind a clump of bushes to take a look; the third, he chatted with him.

After conversing with Machiavelli for many years, I’ve come to think that his early defenders understood him better than we do today. If we read all his works—which include political and military writings, histories, personal letters, diplomatic dispatches, poems, and plays—the main voice that comes through, with remarkable consistency, is quite unlike any of the Machiavellian ones we’ve come to expect. And the more we read, the more obvious it is that Machiavelli enjoyed using his writing to put on a variety of masks, to play with different voices. We shouldn’t forget that he was a brilliant dramatist, not just a student of politics. In his own lifetime he became famous not as a political writer—the Prince and Discourses were published only after his death in 1527—but for his play Mandragola, a blistering satire of corrupt morals in Florence. Like an actor in one of his plays, Machiavelli assumed diverse voices and personas, allowing him to engage with different audiences without offending them. Yet the man behind the various masks was no chameleon, adapting to whatever the times and the men in power might demand. As his closest friends knew well, no one was less likely to compromise what he believed in.

Excerpt from Be Like the Fox: Machiavelli in His World by Erica Benner. Copyright © 2017 Erica Benner. With permission of the publisher, W. W. Norton & Company, Inc. All rights reserved.

Erica Benner lives in Berlin. She is the author of several books, including Machiavelli’s Ethics and Machiavelli’s Prince: A New Reading. Formerly a fellow at Yale University, Benner taught for many years at Oxford University and the London School of Economics.