“Why did you translate Machiavelli, if you didn’t see the point of translating Boccaccio?” Since I wrote about my decision not to retranslate The Decameron, a number of readers have asked me this question. I had explained that I turned down the invitation to retranslate Boccaccio’s wonderful stories because it seemed impossible in modern English to give the text the life and credibility it has both in the original, but also in John Florio’s marvelous version from 1620. Not only was Florio himself a genius, but one senses that the English of his time was closer than ours to the spirit of the events described; it was drenched in religious reference and he was able to say things easily that seem forced or false in our idiom today.

Matters are rather different with Machiavelli, or at least Machiavelli’s Prince. First, it isn’t fiction. He is not intent on evoking the amours of aging abbots or the confessions of witty usurers. Machiavelli, in exile after a long political career and living in the most turbulent times, wanted to say something clear and comprehensible about how power is won and lost—in short, to turn politics into a science. One sentence in particular from his opening dedication to Lorenzo de’ Medici (not Il Magnifico, but a later Lorenzo), reads as both guidance and encouragement for all future translators:

I haven’t aimed for a fancy style or padded the book out with long sentences or pompous, pretentious words, or any of the irrelevant flourishes and attractions so many writers use; I didn’t want it to please for anything but the range and seriousness of its subject matter.

This doesn’t mean, of course, that there aren’t all kinds of rhetorical strategies in The Prince, or that the text shouldn’t be entertaining. But the sense comes first; the language must not get in the way of the argument.

Yet when we turn to the original, language does get in the way and not just for the foreigner who acquired his Italian in his twenties. Written in 1513, The Prince is not easily comprehensible to Italians today. The obstacle is not so much the vocabulary, most of which is still standard in Italian; rather it has to do with extreme compression of thought, obsolete and sometimes erratic grammar, and, above all, a syntax in which subordinate and pre-modifying clauses abound in ways the modern reader is simply not used to.

If you settle down with the original and immerse yourself in it, you do begin to make sense of the author’s claim to straightforwardness. Machiavelli has a spoken, flexible, often brusque voice; but these qualities manifest themselves in ways that seem disorienting to us today. In chapter 21, for example, Machiavelli observes that if your state has two larger neighbors and those neighbors go to war, it is a mistake for you to remain neutral. You have to take sides. Here is Edward Dacres’s 1640 translation, the first to be published in English:

A prince is also well esteemed when he is a true friend or a true enemy; when without any regard he discovers himself in favor of one against another; which course shall always more profit than to stand neuter: for if two mighty ones that are thy neighbors, come to fall out, or are of such quality, that one of them vanquishing thou art like to be in fear of the vanquisher, or not; in either of these two cases, it will ever prove more for thy profit, to discover thyself, and make a good war of it: for in the first case, if thou discoverest not thy selfe, thou shalt alwaies be a prey to him that overcomes, to the contentment and satisfaction of the vanquisht; neither shalt thou have reason on thy side, nor anything else to defend or receive thee. For he that overcomes will not have any suspected friends that give him no assistance in his necessity: and he that loses, receives thee not, because thou wouldst not with thy arms in hand run the hazard of his fortune.

It is all comprehensible enough, but hard work, and it is impossible not to be distracted by old English usages, which drain energy from the argument. At the tricky core of the passage is the moment when Machiavelli says of these neighbouring powers: o sono di qualità che, vincendo uno di quelli, tu abbia a temere del vincitore, o no. Literally, he is saying that the neighboring countries

either are of qualities that, winning one of those, you ought to fear the winner, or not.

Dacres has it:

or are of such quality, that one of them vanquishing thou art like to be in fear of the vanquisher, or not

If we turn to more modern translations, things improve, but not dramatically. Here is W. K. Marriott’s highly respected 1908 version:

they are of such a character that, if one of them conquers, you have either to fear him or not.

This is neither straightforward, nor elegant. George Bull’s 1961 translation for Penguin Classics, which I was being invited to replace, gives:

either they are such that, if one of them conquers, you will be in danger, or they are not.

This is a little closer to modern prose, yet you still can’t help feeling that nobody trying to get this idea across in English today would introduce the second part of the alternative as Bull does by tagging “or they are not” onto the end of the sentence after the interpolation of an “if” clause. If we follow Bull’s general structure but move the “if” clause to the end—“either they are or they aren’t such that if one of them conquers, you will be in danger”—the sentence gains in fluency, but still seems unnecessarily fussy where the original feels brutally direct. I remember looking at this sentence a very long time before appreciating that if one shifted the alternative aspect toward the verb “fear” and away from a description of the two states, the idea remains the same, but can now be expressed much more tersely:

you may or may not have reason to fear the winner

Some time later, the whole paragraph would come out like this:

A ruler will also be respected when he is a genuine friend and a genuine enemy, that is when he declares himself unambiguously for one side and against the other. This policy will always bring better results than neutrality. For example, if you have two powerful neighbors who go to war, you may or may not have reason to fear the winner. Either way it will always be better to take sides and fight hard. If you do have cause to fear but stay neutral, you’ll still be gobbled up by the winner to the amusement and satisfaction of the loser; you’ll have no excuses, no defence and nowhere to hide. Because a winner doesn’t want half-hearted friends who don’t help him in a crisis and the loser will have nothing to do with you since you didn’t choose to fight alongside him and share his fate.

Rightly or wrongly, I fell for the challenge of seeking out these reformulations, looking for every possible way to make the sentences sharp and direct while delivering exactly the sense of the original and keeping the no-nonsense tone. Rather than a liberty, this seemed right in line with Machiavelli’s desire that the work be free of all “irrelevant flourishes.”

But there are other challenges for a translator of The Prince. Written, an English Cardinal claimed, “by Satan’s finger,” and put on Pope Paul IV’s Index of Prohibited Books in 1559, Machiavelli’s little treatise would be blamed for more or less every act of political ruthlessness in Europe over the following two centuries, not least Henry VIII’s dissolution of the monasteries and the St. Bartholomew Day massacre in France in 1572. Very soon “Machiavelli” would be a popular term of denigration; Mach Evil and Mach-a-villain, were typical English corruptions. By the end of the sixteenth century “Machiavellian” was firmly established in the language as an adjective describing cold, clever, immoral calculation.

The result is that translators come to The Prince with prejudices; one is tempted to play to the reader’s expectations, laying on Machiavelli’s supposed cynicism at the expense of the text’s surprising subtlety. Let me give a banal example from Bull’s generally very faithful 1961 translation. At the end of Machiavelli’s account of the rise and fall of the ruthless Cesare Borgia, having explained how he lost power when his father, Pope Alexander, suddenly and unexpectedly died and a pope hostile to Borgia was elected, Machiavelli writes: Raccolte io adunque tutte le azioni del duca, non saprei riprenderlo. Literally: “Having gathered then all the actions of the duke, I would not know how to reprimand/find fault with/reproach him.”

Bull gives: “So having summed up all that the duke did, I cannot possibly censure him.”

Here the word “censure” has a strong moral connotation, and the statement is made stronger still by the introduction of “can’t possibly,” which seems a heavy interpretation of the standard Italian formula “I wouldn’t know how to.” In Bull’s version it seems that Machiavelli is making a point of telling us that he has no moral objections to anything Cesare Borgia did, this in line with the author’s reputation for cynicism.

But if we read the opening line of the next paragraph, it’s clear that Machiavelli is not thinking in moral terms at all: Solamente si può accusarlo nella creazione di Iulio pontefice, nella quale lui ebbe mala elezione. Literally: “The only thing Borgia can be accused of is his role in the election of Pope Julius, where he made a bad choice”; that is, as far as his own interests were concerned, Borgia backed the wrong man, the man who destroyed him. And this brings us to the true nature of the “scandal” of The Prince; it is not that Machiavelli advocates or glorifies immoral behavior; it is that he ignores morality altogether. He is entirely focused on the simple question of how to achieve and hold power, by whatever method. So with The Prince more than with any other text I can remember, it was important never to bring in one’s own moral position, or reaction to Machiavelli’s refusal to assume a moral position, into the translation.

But let’s finish on a lighter note. While translators have played up Machiavelli’s cynicism, they have also been rather prudish about any sexual reference. Machiavelli was a notorious womanizer and in The Prince he believed he was addressing an audience of men who had no worries about political correctness. At the end of his book, discussing the way different personalities will mesh positively or negatively with different circumstances, he observes that there is no one type of person suitable for every situation. All the same, there are certain attitudes that are generally more successful than others; and he comes out with the famous—or infamous—line, la fortuna è donna, et è necessario, volendola tenere sotto, batterla et urtarla. Literally: “fortune is woman and it is necessary, wanting to keep her underneath, to beat her and shove her.”

Clearly the image is a sexual one. Why else would he write “keep her underneath”? Battere and, particularly, urtare were both used colloquially to describe sex, from the male point of view. Like it or not, this is Trump territory. Machiavelli isn’t talking about wife-beating. But many translators are hesitant; Marriot, very cautiously and literally, gives: “fortune is a woman, and if you wish to keep her under it is necessary to beat and ill-use her.” Bull has: “fortune is a woman and if she is to be submissive it is necessary to beat and coerce her.” The sex is gone.

Let me conclude, then, with the whole passage as it came out after endless revisions. No doubt if he were alive today, Machiavelli would see Trump’s triumph as an extraordinary demonstration of the soundness of the advice he gives here: