The Princeas an Enigma: Unraveling Machiavelli’s Intentions
Sam Friedman
Senior Thesis | 2025
Sam Friedman
Mrs. Brown Senior Thesis
The Prince as an Enigma: Unraveling Machiavelli’s Intentions
Niccolo Machiavelli and his body of work have been a subject of fascination for scholars for centuries now, and has become a rather prominent one. ‘Machiavellian’ has entered common parlance, and most people have at least a vague impression of the writer: one defined by unscrupulous cunning and a willingness to do anything to achieve a political goal. This conception however, is rooted in the reading of one text: The Prince. While it is not the longest or most in depth of his political works, The Prince dwarfs all of his other work in both popular and academic recognition. It has influenced political actors across time and nation, and while it was never read by Lorenzo de Medici, its supposed intended recipient, it both influenced and was read by numerous other ‘Princes’, from contemporary monarchs like Henry VIII, revolutionary statesmen like John Adams and Napoleon Bonaparte, 20th century dictators such as Benito Mussolini and Joseph Stalin, and a variety of less notable leaders in between. The Prince has not only influenced statesmen, however. Machiavelli has cemented a place for himself among philosophy’s western canon, eclipsing all other medieval or Renaissance European philosophers. His prominence is especially strange when one considers that Machiavelli himself had a great disdain for classical philosophy. Most introductory political philosophy courses will introduce one to Machiavelli, and invariably focus on The Prince.
Some, however, decide to delve deeper into Machiavelli, and quickly discover that The Prince is something of an outlier among his body of political work. Even the Machiavelli scholars who see it as most similar to his other work still acknowledge the presence of numerous marked differences between it and almost everything else he wrote, even on the same subjects. It is fairly common in studying Machiavelli to compare another work often considered his magnum opus, the much longer and more in depth Discourses on Livy, to The Prince, in an attempt to investigate the reason of The Prince’s eccentricity. However, while it is generally agreed that this discrepancy exists, no one can agree on what causes this discrepancy. Investigating Machiavelli’s writings, life, and political career in search of a definitive solution to this question is a very well trodden path, and someone has argued every possible position. Instead of attempting to reinvestigate from the ground up, this paper will be examining some of the most prominent explanations for the discrepancy and what parts of them work, what parts don’t, what each of them ignores, and possible ulterior motivations for each explanation.
Before one can even begin to think about The Prince, one must consider the extremely volatile Italian political context in which Niccolo Machiavelli felt the need to write it. In the early 16th century, what is now Italy was divided into five major spheres of influence (those of Florence, Milan, Venice, Naples, and the Catholic Church) and many more minor states struggling for power. Although the balance of power between the five was fairly even and none were able to truly gain a significant long term advantage, there were constant conflicts and it was not uncommon for the internal government of one to be completely replaced.
However, each faced threats not only from the other regional powers, but also from the incursions of France, Spain, the Holy Roman Empire, and other unified nations with an interest in taking a part of Italy for themselves. To make matters worse for the Italian powers, each used mercenaries from a more militarily inclined nation to fight their battles, leaving them with no truly loyal military forces.
Machiavelli was born in Florence under Medici rule, and received a much better education than the vast majority of Florentines would have had access to. In his mid twenties, Florence overthrew its Medici rulers and restored the Florentine Republic, and Machiavelli began a rapid ascent through Florence’s public offices, eventually becoming Secretary to the Ten of War, an office in which he undertook numerous diplomatic missions to the leaders of various Italian and European powers, and was an exceptionally devoted patriot to Florence. However, after a decade of service, the Medici family returned to Florence with a mercenary army and restored themselves to power. Machiavelli was arrested for his supposed involvement in a conspiracy to assassinate Giuliano de Medici, and tortured for three weeks before being exiled to his farm outside Florence. In his state of disgrace, he wrote The Prince, and dedicated it to Lorenzo de Medici, the new ‘prince’ of Florence. After completing The Prince, he turned his attention elsewhere, writing much better received plays and poetry, being commissioned to write a history of Florence for Giulio de Medici, and completing his other political treatise, Discourses on Livy.
Written to his friends with the stated goal of conveying everything Machiavelli has learned, Discourses on Livy at its core is a long, detailed discussion of Republics and everything that could possibly be related to their functioning. While some of the contents are also applicable to princely states and made generic for those chapters, the focus is always Republics, and typically, their superiority over princely states. It draws primarily on the history of Machiavelli’s model republic, that of ancient Rome, but also other states and even (although he doesn’t say so) his own experiences and events he bore witness to argue how good states should be run. The strongest recurring arguments emphasize the variety of ways ‘the people’ are more equipped to run a state than a prince, the necessity of maintaining a strong national army of a state's own citizens as opposed to using mercenaries, the necessity of preventing and ways to prevent corruption of the people in a republic and republican institutions, and how the liberty of a republic is maintained or lost. Machiavelli generally does not argue from a moral standpoint. Even when he argues for protecting liberty or a fair justice system, it is from the perspective of what will make the state function better; the goal of everything he advises is the success of a state and the common good of its citizens.
By contrast, The Prince is a much shorter and pithier book addressed to Lorenzo de Medici to help Lorenzo “achieve the summit of grandeur to which your happy destiny and your other capacities predestine you” (Machiavelli, The Prince, 3). It focuses on ‘new princes’, those who gain power over a state or colony through means other than inheritance. Instead of caring about the success of a state, it discusses how one person can gain absolute
power, hold onto it, and use it to unclear ends. The methods recommended are what give the book its shock value and longevity in Europe’s zeitgeist, however. In the middle of the book, which would become its most infamous chapters, after establishing that a prince can only survive if he is not hated by his subjects, Machiavelli begins to discuss how to gain popular appeal. Among the tactics prescribed are to reward one’s friends more than they are owed–in short, to be corrupt–to use the force of the state to nip hatred in the bud, to annihilate one's enemies completely before they can proliferate (although never illegally), to never honor one's promises, to dispose of any servant who has served the prince loyally but also became too beloved or successful though their service, to appear moral but to never be moral, and numerous other excessively violent means. In the final chapter of the book, the end goal to be pursued with these tactics becomes clear. Titled “An exhortation to restore Italy to liberty and free her from the barbarians”, the chapter beseeches Lorenzo to establish a nonmercenary army and conquer Italy, unifying it into one state in his name.
Hopefully the existence and nature of the discrepancy between the two works should be becoming evident, but before defining it, let us examine the consistencies between the works. Both try to be strictly grounded in reality, disdainful of writers such as Plato who imagine ideal societies without regard for what is practically achievable, or heap praise on legendary individuals without acknowledging what they did to become legendary. Both treatises advocate similar military tactics, including but not limited to the not using mercenaries and for maintaining a frequently used standing army. Most notably, both claim that any action, regardless
of morality or justice is legitimate and should be undertaken if it is in defense of ‘the fatherland’. However, even though Machiavelli is known to distort facts or historical examples to fit the point he is trying to make, there are also glaring contradictions between the two works which cannot be easily explained.
The most obvious pieces of evidence for the discrepancy are those where there is a direct contradiction between two statements. For instance, Discourses criticizing hereditary rule while The Prince is largely indifferent to it, praising rulers in The Prince the who he calls tyrants in the Discourses, claiming that no one would conspire to assassinate a popular prince in The Prince while giving extended examples of people doing just that in the Discourses and advising his reader on how to do so successfully, and the like. However, those writing about Machiavelli frequently attempt to explain away these discrepancies as owing to their different subject matters, or different intended audiences. However, there is another more glaring contradiction in the teachings of each book. The Prince invites the unification of Italy under princely rule for the benefit of Italy, while Discourses on Livy argues that princely rule is deleterious to the state being ruled. Machiavelli cannot truly have believed that Lorenzo should become prince of Italy but also that there being a prince would harm Italy, and also have loved his fatherland as he so frequently claims and demonstrates.
To return to the question at hand, how did the apparent discrepancy emerge? The most prominent explanations fall into three main groups: what I will call the political necessity explanation, the satire explanation, and the face value explanation
of The Prince. This is not to say that interpretations within each group are the same, for the most part their arguments are fairly different, but they share at least a similarity in their conclusion. The first group, most notably Isaiah Berlin, argues that the difference is caused by Discourses on Livy being prescriptive, a book defending Machiavelli’s belief for how society should operate. In other words, it explains why republican governments are superior to princely ones and how they should function and how one can make them function using historical evidence to justify his position. For him The Prince is a descriptive analysis, observing how princes and power politics need to function given the sociopolitical circumstances. In this explanation, there is no moral defense nor condemnation of this state of affairs, just a statement of how one must behave to achieve political goals. The second group, most notably Spinoza, Rousseau, and Garrett Mattingly argue that Discourses on Livy is exactly what it claims to be in its dedicatory letter, an earnest expression of what Machiavelli knows and believes to be true. However, they believe The Prince is anything but what it claims to be in its dedicatory letter: instead, they believe it is a non-serious work, either a work of satire to ridicule princes, or a condemning expose on how princes behave in an attempt to show the people the extent of their evil. Finally, the third camp, most notably Harvey C. Mansfield and Leo Strauss, argues that the discrepancy is less real than it appears, that the texts have the same message and that rather than contradicting, they subtly support each other.
To start with the most popular explanation, Isaiah Berlin’s 1971 essay The Question of Machiavelli argues that Machiavelli is operating under two separate systems of ethics: one which is
humanist and confined to private individuals, and one which is amoral and yet necessary to engage in politics. It is his humanist morality which drives Machiavelli’s vision, that of the free and strong republics advocated in Discourses on Livy, and of a united Italy free of foreign mercenaries in The Prince. In Berlin’s words, “If you object to the political methods recommended because they seem to you morally detestable… Machiavelli has no answer, no argument. In that case you are perfectly entitled to lead a morally good life, be a private citizen (or a monk)... in that event, you must not make yourself responsible for the lives of others or expect good fortune; in a material sense you must either be ignored or destroyed” (Berlin, 216). Berlin views The Prince as a work of a sort of proto-realpolitik, one which has matter of factly acknowledged that although a republic would be ideal, it is no longer an option and a strong prince is preferable to disunited decadent republics and a devastated Italy. Berlin believes Machiavelli feels no moral anguish over this course of action, and that the calm acceptance of the reality that there is no ideal or just way of doing politics is what keeps bringing people back to it. The crux of his argument rests on book III part 41 of Discourses on Livy, which says one must disregard considerations of optics, justice, or morality in defense of the survival of one’s fatherland. For Berlin, The Prince is simply expounding on the ugly, amoral, and unjust action necessary to ‘liberate Italy from the barbarians’ using the ethics of the political realm.
Berlin’s explanation is not without its flaws or drawbacks. If Berlin’s analysis is to be believed, and The Prince is an amoral book concerned only with political necessity, it fails to explain why The Prince seems to have moral judgements aplenty which
are not related to their political efficacy. He judges the princes he discusses to be either wicked, like Agathocles, or great and virtuous men, like Cesare Borgia. What makes it more interesting is that they are judged not by the success or necessity of their methods. Agathocles is judged wicked and his modus operandi is called “evil in itself” even when only his successes are mentioned in the book, while Cesare Borgia is judged great despite his immense failure (Machiavelli, The Prince, 27). Furthermore, Berlin ignores a key element of the passage which he quotes from Discourses III 41. Machiavelli writes that when one’s fatherland is in danger, “every other concern put aside, one ought to follow entirely the policy that saves its life and maintains its liberty” (Machiavelli, Discourses on Livy, 301). Berlin focuses entirely on the part concerned with saving the life of the fatherland, while neglecting entirely the maintenance of its liberty. Machiavelli, however, is quick to tell us throughout the rest of the Discourses that princes coming to power in a republic is itself a loss of liberty, and the course of action recommended by The Prince is exactly the type of crisis which Discourses III 41 considers any course of action justifiable to prevent.
The next explanation, best put forth by Garrett Mattingly’s 1958 essay Machiavelli’s “Prince”: Political Science or Political Satire? argues that The Prince is a satire on princes, that it was written not with the intention of persuading or educating Lorenzo, but instead to ridicule him and expose the evil of princes to its nonprince readers with the goal of instructing how to better resist princes. It would not be so out of character for him, as Machiavelli wrote several popular satirical plays later in his life. Mattingly compares it to Johnathan Swift’s A Modest Proposal, noting the
calm, matter of fact tone both deliver their abhorrent advice in. The piece of textual evidence he leans on most heavily is The Prince’s use of Cesare Borgia as a model for princes. In The Prince, Borgia is portrayed as a brilliant, prudent, and virtuous general who would have united Italy if not for atrocious luck. However, Machiavelli worked with him in person during his careers as an ambassador before Borgia’s fall from grace, and in Machiavelli’s reports to his superiors Borgia seems to be an incompetent leader entirely reliant on the support of others as well as a nasty person. Mattingly claims that everyone in Italy in 1513 would have viewed Borgia as an object of ridicule, and that Machiavelli telling Lorenzo to follow his example would have seemed an unsubtle insult to contemporary readers. Mattingly also states that Lorenzo, supported by a pope who was his uncle rather than his father, was similar enough to Borgia for it to be an effective insult. However, the bulk of Mattingly’s argument consists of noting bits of historical context which make the most sense if The Prince is viewed as a satire. Why is devout republican Machiavelli writing a handbook on tyranny? Why do his republican friends not balk at the book? Why, immediately after being exiled, did he write advice for the men he had been accused of conspiring to murder, the men who tortured him for his alleged role in the conspiracy? Why was he connected to a second conspiracy against the Medici after The Prince was written? Finally, why is there no historical evidence that the book, dedicated to Lorenzo de Medici, was ever actually sent to him?
Mattingly’s explanation is also not without its flaws. The parallel to Swift falls short when considering that anyone who reads A Modest Proposal can immediately recognize that it is not
meant to be taken seriously. By contrast, The Prince is only viewed as satire by some of its most historically knowledgeable and careful readers, all of whom had read his other work. If The Prince is a satire, it can’t be regarded as a very good one, considering that when read alone actual tyrants have taken it seriously and used its advice, sometimes to great success. The other reason it can be hard to believe The Prince is entirely a satire is the level of consistency in Machiavelli’s opinions between the two works. If Machiavelli was writing a satire, why would he include his unironic opinions on mercenaries, or fortresses, or military tactics? Furthermore, Machiavelli is willing to misrepresent the historical realities of the figures he uses in his examples to support the point he is making; he does so quite often. Could it make more sense to interpret the false portrayal of Cesare Borgia as an international misrepresentation to support the argument, rather than an ironic insult? It is certainly plausible, and if it is the case, Mattingly does not have any other actual textual evidence to draw on.
The final explanation I will discuss, argued by Harvey C. Mansfield in his 1996 essay The Discourses on Livy and The Prince, asserts that the two texts are not in fact as contradictory as they appear; that Discourses on Livy is a more tyrannical text than it seems and The Prince is a more republican text than it seems. Mansfield argues that The Prince implies that should a tyrant wish for their state and name to live on past their own death, they should turn their state into a republic before they die. According to Mansfield, this is because the bloodlines of hereditary principalities are easily eliminated and forgotten, while republics are harder to destroy and remember and glorify their founders, e.g. Romulus. Conversely, the Discourses argue that to found a
successful republic, one must be acting alone and unjustly, and therefore be a tyrant. However, the tyrannical behavior recommended by the Discourses doesn’t end with a republic's founding. According to Mansfield’s interpretation of Machiavelli, the fact that republics are just results in them making enemies of those who benefit from corruption and injustice, and for liberty to be maintained those who would establish a non-popular rule must be destroyed or made fearful, often through tyrannical means. Furthermore, Machiavelli believes that a republic must have its core modes of functioning frequently reformed to prevent corruption and loss of freedom, and one of the ways this can happen is through extraordinary actions of one person. The implication is Mansfield believes Machiavelli is not instructing Lorenzo on the creation of a principality, but a proto-republic reminiscent of pre-republic Rome; a non-hereditary monarchy with institutions and values which prime it for development into a successful and free republic.
While all of Mansfield’s argument and evidence is generally robust, the conclusions to which it leads are somewhat unusual. Mansfield would have us believe that Machiavelli wrote The Prince essentially solely for Lorenzo, but left all the key information in the subtext, trusting him not only to listen to Machiavelli’s advice but to follow it to the letter to the point that not only he would succeed, but that a state Machiavelli would prefer would emerge. Considering the low esteem Machiavelli held Lorenzo in, and the level of competency he viewed as necessary for this type of endeavor, it is also difficult to believe this was the intention.
Each author also has potential ulterior motives for their explanations, and each explanation has implications as to how we should read The Prince. Both the political necessity and satire explanations attempt to apologize for The Prince and its author in some way–instead of it being a work instructing tyrants on how to do evil things, they justify its prescriptions as either just being politically realistic or not seriously advising at all. Among those I have discussed, only Strauss and Mansfield are adamant that Machiavelli is a ‘teacher of evil’, and that to apologize for him is to make him less valuable and interesting as well as to be wrong. The allure of explaining away Machiavelli’s immorality is that in his work, many find positions they like and wish to defend, or feel the need to defend the writer they have devoted so much time and thought into. In Mansfield’s words, considering The Prince to be a work of dispassionate political science, patriotism, or satire “transform[s] him into a herald of the future who had the luck to sound the tunes we hear so often today–democracy, nationalism or self-determination, and science. Instead of challenging our favorite beliefs and forcing us to think, Machiavelli is enlisted into a chorus of self-congratulation” (Mansfield, Introduction to The Prince, viii). Apologizing for The Prince erases the complexity of the writer and the value of studying him. The other potential motivator for the explanations is justifying The Prince’s place in western canon, despite its seeming out of place due to Machiavelli’s disdain for philosophy and its entirely practical outlook. The Prince tends to be taught as one of the progenitors of the idea that politics has its own set of rules: it is unconstrained by any higher morality or god or justice: what gives a state its authority is its capacity for violence rather than divine right or consent of the
governed, and that politics is simply the struggle to maximize one’s capacity for violence. This place is justified by both Berlin and Mansfield’s positions, but if The Prince is a satire, it loses its value as a work of political philosophy.
Beyond these three explanations, there are many more interpretations that fit into one of these three groups and more still which do not, but I did not judge popular or legitimate enough to include, such as Machiavelli being a visionary Italian patriot writing for the benefit of Italy (Hegel), that The Prince was deliberately bad advice meant to lead Lorenzo to his doom (Mary Dietz), that his work was proto-marxist advice to revolutionaries rather than princes (Engels and later Gramsci), that The Prince is a dispassionate analysis of how politics actually works (Francis Bacon), and that The Prince good and unironic advice to princes (Mussolini). The vast variety of hypotheses is made all the more surprising by the fact that Machiavelli himself tells us why he wrote The Prince, and what it is. In a letter to Francesco Vittori, he writes:
[I have] composed a little work On Princedoms, where I go as deeply as I can into considerations on this subject, debating what a princedom is, of what kinds they are, how they are gained, how they are kept, why they are lost… and by a prince, and especially by a new prince, it ought to be welcomed… there is my wish that our present Medici lords will make use of me, even if they begin by making me roll a stone; because then if I could not gain their favor, I should complain of myself… well may anybody be glad to get the services of one who at the expense of others has
become full of experience. (Machiavelli, Machiavelli and His Friends: Their Personal Correspondence, 128-129)
It appears that The Prince was a groveling attempt to win Lorenzo’s favor and return to Florentine political life, and that Machiavelli took it quite seriously and considered it good advice. In fact, throughout Machiavelli’s correspondence, there is no statement that it is a satire, despite Mattingly’s claims to the contrary, and ample evidence that he legitimately hoped to gain favor through the work.
This being said, the satire explanation still may be the most likely to be the closest to the truth, as both the other explanations still believe him to want what he advocates in The Prince. This is not to say that he was not trying to gain favor, it is abundantly obvious that he was. Nor am I arguing that Machiavelli was not trying to give good advice, but rather that he was placing himself in the shoes of a sycophant to tyrants–he was not saying what he actually believed to be politically necessary, nor how he believed politics actually functions, nor describing the necessary actions for the creation of a republic. He was instead describing the course of action that he would take if he were a new prince (what he would in the Discourses call a tyrant) and only cared for the accumulation of power. In this way it would be a useful resource Lorenzo would appreciate, that while not the most flattering it would prove Machiavelli’s usefulness as an advisor. However, because Machiavelli does not actually believe the course of action he prescribes is how one should govern, and his distaste for princely government bleeds through. The undertone of criticism towards what he advocates is what Mattingly, Rousseau, and Spinoza see
when they call it a work intended to expose the evil of princes to the masses even though it was never intended to be read by the masses, and it is what Berlin and those in his camp see when they attribute the discrepancy to two different systems of morality. The strongest evidence for this position lies in the moral judgement of The Prince’s models. We know his praise of Cesare Borgia is not satirical, as in his Jan 31 1515 letter to Vettori he writes “Duke Valentino, whose deeds I should imitate on all occasions, were I a new prince…”, but we also know his personal disdain for Borgia is real from his diplomatic reports while in Romagna (Machiavelli, Machiavelli and His Friends: Their Personal Correspondence, 313). Even within The Prince there is the problem of Agathocles and his ilk, who are morally judged opposite to how their tactics are evaluated. Finally, there is the insistence in the Discourses that anyone competent and knowledgeable enough to be a successful new prince would know enough to recognize the impossibility of ruling alone for an extended period, and would therefore only set the basic modes and orders, or institutions, of a state before allowing said institutions to allocate power themselves.
Initially, I came into this project planning to apply the analysis of Discourses on Livy to 20th and 21st century politics and see how well it held up, and it is still a subject I would like to further explore going forward. However, over time, I fell into the trap so many who have studied Machiavelli before me have fallen into and become consumed with this question which has puzzled so many for so long. I know better than to believe that I have solved the problem–not even the ability to time travel back and personally ask him would set this question to rest. However, I have ended up with an explanation which at least satisfies and makes sense to me:
Machiavelli believes that The Prince contains good advice to a new prince, but that the very project of a new prince is in itself nigh impossible and morally repugnant, and his nonbelief in The Prince’s project is why he needs to misrepresent the facts so often to support the points he's making, and why there are so many discrepancies between The Prince and Discourses on Livy.
Works Cited
Berlin, Isaiah. “The Question of Machiavelli.” The Prince, W.W. Norton, New York, 1992, pp. 206–236.
Machiavelli, Niccolò. Machiavelli and His Friends: Their Personal Correspondence. Translated by James B. Atkinson and David Sices, Northern Illinois University Press, 1996.
Machiavelli, Niccolò. Discourses on Livy. Translated by Harvey Claflin Mansfield, Univ. of Chicago Press, 1996.
Machiavelli, Niccolò. The Prince. Translated by Harvey Claflin Mansfield, Univ. of Chicago Press, 2006.
Machiavelli, Niccolò. The Prince. Translated by Robert Martin Adams, W.W. Norton, 1992.
Mansfield, Harvey Claflin. “The Discourses on Livy and The Prince.” Discourses on Livy, Univ. of Chicago Press, 1996, pp. xx–xxvii.
Mattingly, Garrett. “Machiavelli’s ‘Prince’: Political Science or Political Satire?” The American Scholar, vol. 27, no. 4, 1958, pp. 482–91. JSTOR, http://www.jstor.org/stable/41208453. Accessed 21 Jan. 2025.