Liberty Matters

Is Machiavelli Friend or Foe to Liberty? (May 2022)

Niccolo Machiavelli remains one of the most contested figures in the history of liberalism. Was he an advocate of republican government, or an adviser to tyrants? Did he preach a politics of fear or a politics of civility? We asked several scholars where they thought Machiavelli's place in this history ought to be. Over the course of this month, you'll hear from a variety of disciplines and perspectives. Whether we can arrive at a definitive answer to our question remains to be seen. We hope you enjoy the conversation.
On the face of it, the answer to the question “Is Machiavelli a Friend or Foe to Liberty” seems relatively straightforward.[1] Over the last 40 years, scholars have placed Machiavelli at the heart of civic humanist and republican traditions of political discourse.[2] Here Machiavelli serves as an important bridge between ancient concerns about political liberty in Greece and Rome and modern concerns about republican and democratic forms of government in nation states. His exhortation at the end of The Prince “to seize Italy and free her from the barbarians” speaks powerfully to contemporary views of political liberty and the nation state. 
From the civic humanist or republican traditions, Machiavelli appears to be a close friend to liberty. In fact, the issue is a complicated one. In this essay, I propose to reassess Machiavelli on liberty by discussing three related issues: Machiavelli’s view of individual freedom in political action; his understanding of the nature of political liberty in free cities; and his problematic treatment of the political liberty of other political communities and of the personal liberties available to individual citizens residing in a “free city.”
Liberty and the Individual
Machiavelli’s goal in writing The Prince is to rethink conventional wisdom on how Princes should act in the world if they want to be successful. He begins by cautioning Princes to understand what their strengths and weaknesses are. Did they come to power by inheriting it (convention), luck (fortune), or skill (virtù)? What approaches should Princes adopt to address their weaknesses? Should they be loved or hated? Generous or stingy? Cruel or compassionate in their actions? In their exercise of power, should they rely on mercenaries or militias? The general thrust of his analysis is to equate freedom of action with independence. Free political actors possess virtù when they are not dependent upon fortune or upon other human beings for their success. To be a free and independent political actor, one must learn to see through the illusions created by others and cultivate one’s own political illusions to manipulate others. As he concludes at the end of Chapter 24, “No method of defense is good, certain, and lasting that does not depend on your own decisions and your own strength [virtù].” (Machiavelli 1994: 74)  
In Chapter 25, Machiavelli extends this discussion of an actor’s freedom in politics when he asks the deeper philosophical question of free will in political affairs. How much of our lives are governed by fortune or God, and how much by our own actions? His answer is revealing: “Nevertheless, since our free will must not be eliminated, I think that it may be true that fortune determines one half of our actions, but that, even so, she leaves us to control the other half or thereabouts.” (Machiavelli 1994: 74) Fortune cannot be completely controlled by any individual, but it can be guided and directed by prudential actions that minimize damage caused by fortune and maximize individuals’ control over their own destiny. The metaphor of building up banks and sluices to control a rampaging river captures the essence of what freedom means to an individual political actor.
Two things are worth noting about Machiavelli’s notion of individual political freedom in The Prince. First, he is not discussing metaphysical freedom but practical freedom in the world of political action. He is not giving philosophical arguments about why an individual possesses free will or how freedom might be attained by adopting a certain religious perspective in this life. His concern is about political action, with a working assumption that free will “may be true” and not that it “is true.” To teach Princes how to be effective in political affairs demands assuming that possessing virtù and attaining independence from fortune and the actions of others is possible. For Machiavelli, we must grant this assumption about free will if we are to have any meaningful control over practical political affairs. 
Second, he merges this discussion of virtuous actors’ ability to control their own destiny with the plight facing contemporary Italy in his time. He writes, “If you think about Italy, which is the location of all these changes in circumstance, and the origin of the forces making for change, you will realize she is a landscape without banks and without any barriers.” (Machiavelli 1994: 75) Machiavelli’s education of an effective and free political actor is part of his desire to create an effective and free political community in modern Italy. As he notes at the beginning of the concluding chapter of The Prince “Italy, so long enslaved, awaits her redeemer.” (Machiavelli 1994: 79)
Political Liberty in the City
Much as The Prince is about creating an effective and independent political actor, The Discourses is about building a virtuous people capable of making their city effective and independent in international affairs. A free city is one that is self-governing and independent of outside influences important to affairs of state. Citizens are free through their participation in the institutions of a free city. A city’s success is measured by its ability to impose itself on other communities and to survive over time. Creating a virtuous city is much more complicated than creating a virtuous Prince. To engage in free political actions, Princes need to be taught how to look at the world properly so that they might act effectively in a world of ongoing change. In contrast, cities need institutions and religious practices to instill virtù into the citizenry, enabling them to remain committed to the public good, rather than to narrow interests that promote factionalism in public life. The practical problem facing legislators of great cities is learning how to establish religious practices and political institutions that instill virtù into the people as a whole and make the city free and self-governing over an extended period. 
In his analysis of the institutions and practices of the Roman Republic, Machiavelli makes numerous contributions to our understanding of political freedom. Three stand out. First, he takes seriously the idea that in political life we “should assume that all men are wicked and will always give vent to their evil impulses whenever they have the chance to do so.” (Machiavelli 1994: 92). Other than the belief in the importance of a free city, there is no place for sentimentality in Machiavelli’s view of man or the city. Second, his analysis of political freedom highlights the importance of constitutional, religious, and educational practices. If free cities are to survive over time, they need anchoring in the principles and practices that made them great at their founding. They must return to these founding principles and practices periodically through political reforms or institutional innovation. Third, he argues that tensions and conflicts found in a city can serve the public good by making the city stronger. Mixed government that balances aspects of monarchical, aristocratic, and democratic regimes can be more effective and powerful than any one pure regime. Checks and balances in the constitution of a city can foster political freedom domestically and internationally by making the city more powerful. One key for Machiavelli is to identify the group in the city that has an interest in protecting the liberty of the city. “Depending on whether this task is entrusted to the right group or not, political liberty will be preserved for a longer or shorter period of time.” (Machiavelli 1994: 95) In practical terms, this means deciding whether a city’s goal is simply to defend itself from outside forces (as was the case of republics like Sparta and Venice) or to impose itself on others through territorial expansion (as was the case in Rome). The former relied on the elite for maintaining political liberty; the latter depended upon the populace.
The Limits to Machiavelli’s Vision of Liberty
Machiavelli’s vision of liberty is flawed in two important ways, one involving international affairs, the other domestic affairs. First, in Machiavelli’s eyes the Roman Republic and its citizens were free because they could impose their will upon other political communities. Roman freedom in international affairs involved the oppression of others. Political freedom was, in this regard, a zero-sum game with one winner and many losers. Why should my nation’s political freedom constrain your nation’s freedom? Machiavelli suggests that inwardly looking cities like Sparta and Venice might offer an alternative to expansionist Rome, but their elitist politics bred discontent and class conflict that threatened the stability of both cities. (see Machiavelli 1994: 96) In a pluralistic world, it is increasingly difficult to accept Machiavelli as the final word about political liberty in international affairs.
A second limitation is equally problematic. There is no space in Machiavelli’s thought for a modern notion of a society composed of free individuals pursuing different private concerns and values.[3] Nor is there any sense that such individuals might have the right to govern their own private lives, actions, or property freed from the interference of the city. In Machiavelli’s world, order does not emerge from the experiences or actions of individuals voluntarily coming together to promote their own ends in their everyday lives. Order is imposed from the top down through the actions of an independent Prince or the institutions of a self-governing virtuous community. Liberty for the citizen is acquired through participation in a larger community that is self-governing and independent, not a condition of being left alone by that community to pursue one’s personal vision of happiness.
In 1815, Benjamin Constant drew an important distinction between ancient and modern forms of liberty that is relevant to my assessment of Machiavelli’s view of liberty. He writes, “The freedom of ancient times was everything which assured the citizens the biggest share in the exercise of political power. The freedom of modern times is everything which guarantees the citizens independence from the government.” (Constant: 361). Seen in this light, Machiavelli is a close friend to ancient notions of political liberty. But he remains, at best, a distant acquaintance to modern notions of liberty where personal liberty is valued alongside a variety of other modern forms of political liberty including the vote and the rule of law.
Bock, Gisela, Quentin Skinner, and Maurizio Viroli. 1990. Machiavelli and Republicanism. Cambridge: Cambridge University Press.
Colish, Marcia L. 1971. “The Idea of Liberty in Machiavelli.” Journal of the History of Ideas. Vol. 32. No. 3: 323–350.
Cavallo, Jo Ann. 2014. “On Political Power and Personal Liberty in The Prince and the Discourses.” Social Research. Vol. 81. No. 1: 107-132.
Constant, Benjamin. 2003. Principles of Politics Applicable to All Governments. Edited by Etienne Hoffman. Translated by Dennis O’Keefe. Introduction by Nicolas Capaldi. Indianapolis: Liberty Fund.
Hörnqvist, Mikael. 2004. Machivelli and Empire. Cambridge: Cambridge University Press.
Machiavelli, Niccolò. 1988. Florentine Histories. A New Translation by Laura F. Banfield and 
Harvey C. Mansfield, Jr. With an Introduction by Harvey C. Mansfield. Princeton: Princeton University Press. 
Machiavelli, Niccolò. 1994. Selected Political Writings. Edited and translated by David Wootton. Indianapolis: Hackett Publishing Inc. 
Machiavelli, Niccolò. 1996. Discourses on Livy. Translated by Harvey Mansfield and Nathan Tarcov. Chicago: University of Chicago Press.
McCormick, John P. 2018. Reading Machiavelli: Scandalous Books, Suspect Engagements and the Virtue of Populist Politics. Princeton: Princeton University Press.
Pettit, Philip. 2011. “The Republican Ideal of Freedom.” In David Miller, ed. The Liberty Reader. London and New York: Routledge. Pp. 223-242.
Pocock, J.G.A. 1973. Politics, Language and Time: Essays on Political Thought and History. New York: Atheneum.
Pocock, J.G.A. 1975. The Machiavellian Moment: Florentine Political Thought and the Atlantic Republican Tradition.
Pokhovnik, Raia. 2011. “An Interview with Quentin Skinner.” Contemporary Political Theory. Vol. 10, 2, 273-285.
Rahe, Paul A. 2006. Machiavelli’s Liberal Republican Legacy. Princeton: Princeton University Press.
Shaw, Carl K.Y. 2003. “Quentin Skinner on the Proper Meaning of Republican Liberty.” Politics. Vol. 23. No. 1: 46-56.
Skinner, Quentin. 1978.  The Foundations of Modern Political Thought. 2 vols. New York: Cambridge University Press.
Skinner, Quentin. 1981. Machiavelli. New York: Hill and Wang.
Skinner, Quentin. 1998. Liberty Before Liberalism. New York: Cambridge University Press.
Skinner, Quentin. 2006. “A Third Concept of Liberty.” In David Miller, ed. The Liberty Reader. London and New York: Routledge. Pp. 243-254.
Viroli, Maurizio. 2014. Redeeming the Prince: The Meaning of Machiavelli’s Masterpiece. Princeton: Princeton University Press.
[1] Colish (1971) provides an excellent analysis of the ways that the idea of liberty is used in Machiavelli’s various works. 
[2] There is an enormous literature on Machiavelli’s place in civic humanist and republican political discourse. See Pocock (1973, 1975), Skinner (1978, 1981, 1998, 2006). See also Pettit (2011), Shaw (2003), Viroli (2014), Hörnqvist (2004), and Bock, Skinner, and Viroli (1990). Pokhovnik (2011) provides Skinner’s reflections on the evolution of his interpretation of republican and neo-roman thought out of the work of Machiavelli. For readings that situate Machiavelli in alternative interpretive frameworks see McCormick (2018, chapter 6), Rahe (2006), and the editors’ introductions to Machiavelli (1988, 1994, 1996).
[3] I disagree with Colish (1974: 345-346) and Cavallo (2014) who argue that Machiavelli “clearly identifies freedom with the protection of private rights.” (Cavallo: 107). Concern over personal liberty is, at best, marginal for Machiavelli. The thrust of his argument is about the liberty of the city and the political freedom provided to citizens by the city. He does not offer any systematic way for understanding the autonomous rights of individuals or the operations of what we might call a “civil society.” 

Response Essay Is Liberty a Means or an End?

The course of the Roman republic demonstrates extremely well how difficult it is, in ordering a republic, to provide for all the laws that maintain it free.…[I]f those cities that have had their beginning free and that have been corrected by themselves, like Rome, have great difficulty in finding good laws for maintaining themselves free, it is not marvelous that the cities that have had their beginnings immediately servile have not difficulty but an impossibility in ever ordering themselves so that they may be able to live civilly and quietly.[1]
Liberty is not the default state for a society. Looking at 16th century Italy in The Prince and the early years of the Roman Republic in Discourses on Livy, Machiavelli amply demonstrates liberty was indeed a very tenuous thing. Regardless of whether authority in a country is nominally lodged in a prince or the people, liberty is always at risk.
How, then, can a society achieve liberty? Having achieved it, how can liberty be preserved? Enter Machiavelli, who explains that since liberty does not arise and maintain itself, it needs the help of an enlightened ruler. He offers his counsel, like the friend who cares enough about you to tell you what you really do not want to hear. To enable a society to live in freedom requires someone willing to do hard, and often unpleasant, work.
How unpleasant in the work of establishing and maintaining liberty? You should not get into this business if you want to keep your hands clean. “This will always be known by those who read of ancient things: that after a change of state, either from republic to tyranny or from tyranny to republic, a memorable execution against the enemies of present conditions is necessary.”[2] A memorable execution is necessary? That is blood, not dirt, on the hands of the ruler. A free state creates many enemies, which inevitably create problems for the ruler. “If one wishes to remedy these inconveniences and the disorders that the difficulties written above might bring with them, there is no remedy more powerful, nor more valid, more secure, and more necessary, then to kill the sons of Brutus.”[3] Who were these sons of Brutus? Lucius Junius Brutus overthrew the last of the Roman kings and established a republic in 509 BC. His own sons soon joined a plot to bring back the monarchy. Once discovered, Brutus’ sons were flogged and beheaded while their father watched. Machiavelli approves. 
What good comes of these executions? In yet another rather revealing anecdote Machiavelli demonstrates the objective. A duke wanted to pacify an unruly region.
So he put there Messer Remirro de Orco, a cruel and ready man, to whom he gave the fullest power. In a short time Remirro reduced it to peace and unity, with the very greatest reputation for himself. Then the duke judged that such excessive authority was not necessary, because he feared that it might become hateful; and he set up a civil court in the middle of the province, with a most excellent president, where each city had its advocate. And because he knew that past rigors had generated some hatred for Remirro, to purge the spirits of that people and to gain them entirely to himself, he wished to show that if any cruelty had been committed, this had not come from him but from the harsh nature of his minister. And having seized this opportunity, he had him placed one morning in the piazza at Cesana in two pieces, with a piece of wood and a bloody knife beside him. The ferocity of this spectacle left the people at once satisfied and stupefied.[4]
One can well imagine that having seen a ruthless and cruel ruler thus dispatched, the people felt an overwhelming sense of freedom from cruel tyranny. 
Machiavelli patiently explains, page after page, that achieving and maintaining liberty sometimes requires illiberal means. Indeed, a society which wants to be free must prepare for the day of trouble in which it needs to abandon its freedom. “So a republic will never be perfect unless it has provided for everything with its laws and has established a remedy for every accident and given the mode to govern it. So, concluding, I say that those republics that in urgent dangers do not take refuge either in the dictator or in similar authorities will always come to ruin in grave accidents.”[5]
As Machiavelli proceeds in his analysis of good statecraft, one begins to notice the contradiction. If preserving liberty means frequently resorting to illiberal methods, what exactly is the difference between living in a free state and living under a tranny? Is the difference purely the relative number of atrocities? 
We begin to see the solution to this puzzle of whether liberty can only be maintained by illiberal means when we observe why Machiavelli thinks people care about freedom. The people’s interest in liberty is extremely parochial. “[T]he common utility that is drawn from a free way of life is not recognized by anyone while it is possessed: this is being able to enjoy one’s things freely, without any suspicion, not fearing for the honor of wives and that of children, not to be afraid for oneself.”[6] As Machiavelli observes in The Prince, a ruler can avoid becoming hated “if he abstains from the property of his citizens and his subjects, and from their women.”[7] For Machiavelli, this is the entire extent of the blessings of liberty. It is not freedom of speech or religion or the press or assembly or trial by jury that matters to people. It is simply making sure their bank accounts and spouses are not appropriated by the rulers.
The error of thinking that Machiavelli is acting as a friend to liberty arises because we have not been clear about the nature of liberty in his writings. For Machiavelli, liberty is a means, not an end. He attributes the source of thinking of liberty as a means to the people themselves. A ruler “should examine what causes are those that make [peoples] (sic) desire to be free. He will find that a small part of them desires to be free so as to command, but all the others, who are infinite, desire freedom so as to live secure.”[8] Security, not liberty, is the desired end.
If liberty is a means and not an end, it explains everything that Machiavelli has counseled above. While Machiavelli never actually explicitly said the ends justify the means, it is not farfetched to attribute such a sentiment to him. If liberty is useful in attaining the end of secure society, then by all means, liberty should be promoted. But, at the first sign that liberty is not a useful means, it should be abandoned hastily. 
Far from being that ever honest friend to liberty telling us what we do not want to hear, Machiavelli is the serpent in the garden, whispering sweetly in the ears of a would-be ruler that the appearance of supporting liberty is a good means to achieving and maintaining power. In talking about whether a ruler should be morally good, Machiavelli notes:
[It] is not necessary for a prince to have all the above-mentioned qualities in fact, but it is indeed necessary to appear to have them. Nay, I dare say this, that by having them and always observing them, they are harmful; and by appearing to have them, they are useful, as it is to appear merciful, faithful, humane, honest, and religious, and to be so; but to remain with a spirit built so that, if you need not to be those things, you are able and know how to change to the contrary.[9]
In exactly the same way, it is more important to appear to care about liberty than to actually make that the end toward which you are striving. 
Machiavelli’s influence is thus quite pernicious. The ruler who comes to power with the promise of bringing liberty is soon corrupted. Machiavelli is quick to note “how easily men are corrupted and make themselves assume a contrary nature, however good and well brought up.”[10] But, this path to corruption is made easier by Machiavelli’s frequent reminders that abandoning liberty sometimes really is necessary: “Whoever takes up the governing of a multitude, either by the way of freedom or by the way of principality, and does not secure himself against those who are enemies to that new order makes a state of short life.”[11]
Sadly we have seen Machiavelli’s influence in generation after generation. By encouraging us to think about liberty as a means rather than an end, Machiavelli has made it all too easy to abandon the commitment to liberty whenever more convenient means come along to achieve desirable ends. 
Machiavelli, Niccolo (1996) Discourses on Livy, Harvey Mansfield and Nathan Tarcov, translators, University of Chicago Press.
Machiavelli, Niccolo (1998) The Prince, Harvey Mansfield, translator, University of Chicago Press.
[1] Machiavelli, Discourses on Livy, I 49
[2] Machiavelli, Discourses on Livy, III 3
[3] Machiavelli, Discourses on Livy, I 16
[4] Machiavelli, The Prince, VII
[5] Machiavelli, Discourses on Livy p. I 34
[6] Machiavelli, Discourses on Livy, I 16
[7] Machiavelli, The Prince, XVII
[8] Machiavelli, Discourses on Livy, I 16
[9] Machiavelli, The Prince, XVIII
[10] Machiavelli, Discourses on Livy, I 42
[11] Machiavelli, Discourses on Livy, I 16

Response Essay Liberty Is an Unconquered Country: Machiavelli’s The Prince and Liberty

As I write this, a European country whose land has been fought over for centuries is again battling for its existence against an invader. The question of the basic conditions for liberty leaps to mind and, in considering whether Machiavelli is a friend or foe to liberty, one of his most difficult writings preoccupies me. More strongly than usual I see The Prince as born out of the twin existential crises of its author and of Italy herself.
It seems central to the question of whether Machiavelli supports liberty to consider the traumatized condition of Renaissance Italy. In a place where life and property are suddenly forfeit, what does liberty mean? Whose liberty are we talking about? What answer, if any, does the renaissance context help us see? 
Italy was subject to repeated external conquest and internal conflict between city-states over territory. In Machiavelli's lifetime six major Italian states invade one another, assassinate one another's leaders, and foment revolutions among one another's people. Naples has five different kings in less than two years. Northern Italy falls to the French, who are then defeated by the Emperor Charles V. Rome is sacked by Charles’ mercenaries, Castiglione is taken captive, and Machiavelli dies, all within a few months. Italy has become a depopulated battlefield.
Machiavelli’s life parallels Italy’s. In his own Florence, Medici rule is shaken when Machiavelli is 9, and they are expelled when he is 25. Machiavelli serves the republic that follows as defense minister, ambassador, and later as historian. When the Medici roar back, he is imprisoned and tortured. Exiled from his city, recovering from torture, writing his Discourses on the Roman historian Livy with the ruins of the Roman empire all around him, desperate for employment, and positioning himself against both brilliant contemporaries like Baldassare Castiglione and past greats like Dante and Petrarch, Machiavelli creates The Prince. His most famous work, it most often seems to present the greatest difficulty for those hoping to prove that he defends liberty. 
Fourteenth-century Florentine political factionalism had sent the poet Dante into exile, to dream of a new Charlemagne who might conquer, and reunite, Italy. That dream endured, inspiring a fundamental question underlying The Prince. How was it possible that the peninsula that had once conquered the known world and held it for centuries, whose renaissance artists, poets, bankers, architects, and philosophers had captured the imagination of all of Europe, could not master itself?
The Prince’s answer troubles the mind more than Machiavelli’s Discourses does. It encourages rulers to abandon classical and Christian virtues in order to maintain power. It suggests that a ruler emulate animals (rather than saints). “Ancient princes,” it claims, “were given to Chiron the centaur to be raised . . . To have as teacher a half-beast, half-man” because a prince has to “know well how to use the beast. . .”.
The Prince advises killing entire royal families. It commends Cesare Borgia for having a subordinate pacify Romagna, then leaving him “in the piazza . . . in two pieces, with a block of wood and a bloody knife beside him.” It advises what sounds like hypocrisy: it’s not necessary to have traditional virtues, but instead “necessary to appear to have them. . . . [by] always observing them, they are harmful, and by appearing to have them, they are useful, as it is to appear merciful, faithful, humane, honest, and religious, . . . but to . . . know how to change to the contrary.” A prince “cannot observe all those things for which men are held good, since he is often under a necessity to maintain his state, of acting against faith, against charity, against humanity, against religion.” And, of course, Machiavelli proves that “it is much safer to be feared than loved,” because fear can be compelled. 
This is pretty strong meat. What does it say about liberty, though? 
Machiavelli points out the importance of perspective: the people can understand the prince and the prince can understand the people better than either can understand themselves. And perhaps, if it isn’t too postmodern to suggest it, liberty in The Prince needs to be seen from different angles: liberty for the people, liberty for the powerful (“the great”), and liberty for the prince. 
Because the prince needs the people, he will have to secure them these liberties: enough stability to run their businesses and families safely and a stable tax environment that is not excessive or punitive; he must also not take the women to use as sex toys. Droit de seigneur is not a right for Machiavelli’s prince.
In fact, the prince appears to have all the liberty power grants, but he cannot use it. His liberty is restricted to choices focused on staying alive and in power. He is bound by fear. Every moment of his life must focus on war and self-defense. His appearance must be rigidly controlled. Alliance and fidelity can kill. Friendship is impossible. Lieutenants fail. The prince must be an obsessive micromanager, and it is difficult to imagine when he sleeps. Abdication means death; a successor would destroy all rivals. Machiavelli does not mention marriage or children; their absence from The Prince suggests that even those must be eschewed. After all, Liverotto da Fermo assassinated his surrogate father, so having children destroys princes. The practice of Christian faith is dangerous, so the Christian heaven is denied. No friends, no love, no allies, no assistants, no sleep, no leisure, no offspring, no fame, no salvation. Machiavelli sacrifices the individual liberty of the prince to make the civil liberties of the people possible.
In many ways, Machiavelli’s prince seems merely a tool for securing the people’s liberty, especially against the great, because the people only want liberty, while the great desire enough power to destroy others, including the prince: “One cannot satisfy the great with decency and without injury to others, but one can satisfy the people; for . . . the great want to oppress and the people want not to be oppressed.” Machiavelli advises that the great be granted little liberty, little power, and little future.
Machiavelli is not the only contemporary writer worried about the great. Castiglione’s Book of the Courtier looks to prevent precisely these dangers to, and from, them. Castiglione wants to make rivalrous “renaissance men” into counselors to princes, because:
Without restraint [princes] . . . do not tolerate friendships or societies or common interest among the citizens; instead they foster spies, informers and murderers, to create terror . . . cause the wretched people endless loss and ruin, and often enough ensure the cruel death of the tyrant himself or at least cause him to live in a state of perpetual fear. 
For Castiglione, who reminds us that princes can only sleep safely in a chest or suspended in midair, the prince both is, and is in, the greatest danger. However, the prince’s courtier may ensure everyone’s safety: “if he knows that his prince is of a mind to do something unworthy, he should be in a position to dare to oppose him, . . . to remove every evil intention.” 
The prince must be restrained. For Machiavelli that restraint is internal, fear of assassination; for Castiglione the restraint is external, the benevolent courtier. Both express the yearning of Italians for the peace and stability that ensure the people’s liberty to trade, associate freely, build a business, have families, and create without interference. Where there must be a prince, and where there must be the great, they must be bound -- or eliminated -- to secure the liberty of the people.
And yet a prince may serve a purpose. Dante dreamed of a new Charlemagne to unite and defend Italy; Castiglione yearned for a past when the Duke of Urbino provided liberty discourse to his court; The Prince dreams of one, stable Italy. Fulfilling that dream requires a sovereign to “heal her wounds, and put an end to the sacking,” to stop her tribute to foreign conquerors, “and cure her of her sores.” The Prince ends screaming, “this barbarian domination stinks to everyone.” The weakness of Italy “follows from the weakness at the head,” and she lacks one sovereign, whose sword Machiavelli expects to see turned not against the people, as Hobbes would allow, but against outside invaders and the great. 
Machiavelli borrows Petrarch’s voice for his conclusion: “Virtue will take up arms against fury/and make battle short/because the ancient valor in Italian hearts/is not yet dead.” In the middle of the Canzoniere’s amorous introspection, Petrarch demanded, “what are so many foreign swords doing here?” The end of Petrarch’s canzone grounds The Prince: “’Who will protect me? I go crying: Peace, peace, Peace!’” 
Would Machiavelli’s prince, living in fear, chained for survival to his people, guarantee their liberty in the real world? I don’t know. But the cry of late medieval and renaissance Italy echoes in the cries of Europe today for an unconquered country and the liberty it provides. It is the cry of human nature when in free fall, whatever the commitment to liberty. 
Castiglione, Baldassare. The Book of the Courtier. Translated by George Bull, Penguin Books, 1967/1976.
Machiavelli, Niccolò. The Prince. Translated by Harvey C. Mansfield, U Chicago Press, 1985/1998.
Petrarch, Francesco. Petrarch’s Lyric Poems: The Rime Sparse and Other Lyrics. Translated by Robert M. Durling, 1976. 

Response Essay Is Machiavelli a Friend or Foe of Liberty?[1]

Machiavelli certainly believes he is a friend of liberty. Indeed, liberty is an important concept in Machiavelli’s political philosophy, but what precisely does he mean by it? This is no easy topic to unpack. My aim is not to break new ground but to offer a brief survey of some of the various uses of liberty in Machiavelli’s political thought.
Thankfully, Marcia L. Colish provides a helpful framework from which to begin. In her 1971 article, “The Idea of Liberty in Machiavelli,” Colish identifies four kinds of liberty in Machiavelli’s political thought:
  • liberty in the commonplace sense,
  • liberty as free will,
  • corporate liberty, and 
  • liberty within the state.
For the most part, I will follow her framework, but I shall add a fifth kind—one which Machiavelli develops in his comedy, the Mandragola—namely, sexual freedom. In this work, Machiavelli seems to argue for a freedom from the authority of God to do with our bodies as we please (provided all partners consent and no one’s body or reputation is harmed). But before turning to develop Machiavelli’s notion of sexual freedom—which in many ways assumes familiarity with some of the other notions of liberty—it is necessary to say a few words about Machiavelli’s other senses of liberty first.
Liberty in the Commonplace Sense[1]
Colish describes how Machiavelli uses “liberty” in a generic way to denote a variety of concepts, such as a person’s freedom from captivity, for example, or an individual’s financial independence, or a ruler's freedom for political action. The last is a particularly interesting example. According to Machiavelli, the best defense against political instability and conspiracies is for a wise ruler to avoid antagonizing the ambitious while keeping the people content. 
In Chapter 19 of The Prince, Machiavelli associates liberty with a set of laws and institutions that provide a ruler with the necessary freedom for political actions that help him to avoid being held in contempt by his subjects. Machiavelli draws upon the French monarchy to illustrate his point. In France, for example, the Prince can use the judiciary to avoid blame by using the judiciary to play the nobles and the people off of each other, simultaneously checking the destructive power of each. The French “Parliament”—a “law court,” not a legislative body—is ordered in such a way that it restrains the nobles and “their insolence.” The one who “ordered that kingdom” recognized that ambition must be checked by ambition. In Machiavelli’s words, “knowing the hatred of the generality of the people against the great [the nobility], which is founded in its fear,” the one who ordered this constitution also found a way of gaining the trust of the people by ordering government to favor the general populace. Being so ordered, the French constitution protected the prince “from the blame he would have from the great when he favored the popular side, and from the popular side when he favored the great,” thus freeing him to take action that favored the liberty of France. According to Machiavelli, “this order could not be better, or more prudent, or a greater cause of the security” and liberty of the prince, because such an arrangement would place the ruler above criticism by shielding him from accusations of favoritism.
Free Will
Statesmanship requires prudence and free will. Otherwise, individuals are reduced to mere passive spectators of determined political events. In Chapter 25 of The Prince, Machiavelli considers, “How much fortune can do in human affairs, and in what mode it may be opposed.” In this chapter, he breaks with the “many” who “have held and hold the opinion that worldly things are so governed by fortune and by God, that men cannot correct them with their prudence, indeed that they have no remedy at all.” Machiavelli addresses whether human beings possess any liberty over their lives. What place is there for prudence, if humans are subject to chance and God, Machiavelli wonders. He writes, “in order that our free will not be eliminated, I judge that it might be true that fortune is arbiter of half of our actions, but also that she leaves the other half, or close to it, for us to govern.” The conclusion is obvious: God plays a minimal role in our lives, thus leaving prudence and virtue to manage the rest. By reducing the role of God in human affairs, Machiavelli doubts there are any limits placed upon human intelligence. Rather than succumbing to a deadly fatalism when nature strikes, human beings can use prudence to provide against such exigencies. For example, though “violent rivers” may “flood the plains,” Machiavelli asserts that it “is not as if men, when times are quiet, could not provide for them with dikes and dams so that when they rise later, either they go by a canal or their impetus is neither so wanton nor so damaging.” (It is easy to see how someone like Francis Bacon could pick up on this idea and conclude that philosophy at its finest is the conquest of nature.)
Corporate Liberty
Machiavelli is of course concerned about national sovereignty; Colish calls this “corporate liberty.” A nation is free when it lives under its own laws and customs (for Machiavelli the clearest examples being the German free cities and the Swiss). However, a nation’s sovereignty largely depends on the strength, discipline, and organization of its military. According to Machiavelli, a nation cannot remain free and thus sovereign if it hires foreign mercenaries rather than possessing its own arms. In Chapter 13 of The Prince, for example, Machiavelli asserts that “without its own arms no principality is secure; indeed it is wholly obliged to fortune since it does not have virtue to defend itself in adversity.” Citing Tacitus, Machiavelli states, “and it has always been the opinion and judgment of wise men ‘that nothing is so infirm and unstable as the reputation of power not sustained by one’s own force.’” 
Liberty within the State
Machiavelli’s most sustained treatment of liberty for citizens within the state is found in his Discourses on Livy. According to Machiavelli, men “however good and well brought up,” are easily corrupted by a little power and ambition. The prudent lawgiver, he says, ought to avoid a constitution that relies on the virtue of each ruling element in one of the three simple forms of government: monarchy, aristocracy, or democracy. Instead, Machiavelli advises a wise founder to choose a mixed constitution “that share[s] in all [forms of government], judging it firmer and more stable, for the one guards the other.” Machiavelli attributes Roman liberty to Rome’s mixed constitution, which managed the internal strife between the plebs and the nobles through institutional “checks” without completely sapping the citizens’ energies, thereby maintaining a republic fierce and largely balanced. Indeed, Machiavelli argues that the “tumults between the nobles and the plebs” is “the first cause of keeping Rome free,” the office of the tribunate playing a uniquely critical role. Machiavelli calls the creation of the tribunes in Rome the cause of its “perfection,” as it gave Rome a full complement of modes: rule of one by the consuls, rule of the few by the Senate, and rule of the many by the tribunes. The representation of the people through the tribunes naturally served as a check on the “insolence of the nobles.” Rome’s liberty relied on the ability of the state to continually manage the tumults between the people and the senatorial class. 
Sexual Liberty
According to Cicero, the laws governing theater and music “cannot be changed without bringing a change in the laws of the state.” Although he admits that the arts helped to civilize Rome, Cicero, like Plato and Aristotle before him, is nevertheless wary of the influence of music and theater on the morals of the state. Ancient Greece, he observes, used to punish those who performed music that would cause the “audience to rock to and fro jerking their necks and eyes in time with the inflections of the singer’s voice,” because music has the power to “infect” citizens “with pernicious crazes and pernicious ideas [that] would suddenly bring about the collapse of entire states.” Hence, in the Republic, Cicero elaborates on the damage done by dramatists, pointing out that “since [the ancient Romans] regarded the theater and show business in general as disgraceful, they thought that such people should not only be deprived of the public offices enjoyed by other citizens but should also be removed from their tribe by the censor’s stigma.”
By contrast, in his comedy Mandragola, Machiavelli introduces a new concept of liberty: sexual liberation. The play centers around a wealthy old man, Nicias, and his much younger and beautiful wife, Lucrezia. But there is a problem: Nicias wishes to have a child and heir, but he is infertile. The solution, as Machiavelli sees it, is sexual liberty. At the outset of the play, Machiavelli proclaims that there are certain “tricks to the world” that can be used to help the audience achieve their desired ends, which he takes to be erotic desire. Once his audience learns these “tricks,” he explains, it is possible for anyone to satisfy their urges while maintaining order and a good public reputation. The “trick” is figuring out how to successfully satisfy one’s wishes by learning how to help others satisfy theirs. Such a scheme works, Machiavelli suggests, so long as everyone conspires together to keep up appearances by maintaining publicly respectable decorum and by refusing to upset the political order. 
In the comedy, a young man named Callimico falls in love with Lucrezia and is determined to win her over. The problem, of course, is that Lucrezia is married and virtuous. Callimico, however, hatches a plan with a friend. Callimico pretends to be a doctor with a solution to Nicia's troubles. He claims to have a potion made from mandrake that will result in pregnancy. There is only one problem: the first person to sleep with her after she ingests the potion will die the following day. Callimico convinces Nicias to find someone to sleep with his wife and, with a fitting disguise, manages to be that someone. Her virtue somewhat tarnished, Lucrezia is able to provide her sterile husband with an heir by sleeping with a younger man. The play celebrates her adultery by focusing on the good effects of her deed, namely, providing her husband with a child. By demonstrating the usefulness of sexual liberty, Machiavelli frees his characters, not just from the shame of public opinion, but also from the Church’s authority over marriage by undermining the notion that marriage is a holy sacrament.
Machiavelli sees himself as a friend of liberty. He uses liberty in a variety of ways in order to enlighten nations and individuals on how, through the strength of their own intelligence and will, they may achieve sovereignty and control over their lives.
[1] I wish to thank Sarah Weaver and Joshua Robe for their helpful comments and feedback on earlier drafts.

Conversation Comments Is Machiavelli a Friend or Foe to Liberty?: Reflections on My Colleagues’ Essays

The four essays in this collection are a good indication of the varying responses that people interested in the idea of liberty can have to Machiavelli’s thought. 
Habib, relying upon the 1971 essay of Marcia Colish, summarizes the ways that liberty is used in Machiavelli’s thought. Through a reading of Machiavelli’s play Mandragola, Habib argues that one also can find an argument for sexual liberation along with other kinds of liberty identified by Colish. I find this approach to understanding Machiavelli’s contribution to the study of liberty to be helpful but needlessly limiting. Like Colish, Habib offers a list of how Italian words standing for liberty are used in Machiavelli’s work without explaining what these distinctive usages tell us about the larger idea of liberty that might tie them together. Habib’s conclusion that using liberty in a variety of ways makes Machiavelli a “friend of liberty” is suggestive but needs expansion. 
Hull’s essay draws attention to the parallels between Machiavelli’s times and our own. A self-governing free political community must be powerful enough to throw off the oppression of outside forces. To be a free self-governing city demands political leaders that act and make difficult, even horrific, decisions.  While Hull welcomes Machiavelli’s discussion of the problem of liberty in the Discourses, she seems to be troubled by some of the arguments about the use of power to achieve political freedom in The Prince.  Her essay concludes with a reflection on Machiavelli’s use of the quote from Petrarch at the end of The Prince: “Virtue will take up arms against fury/and make battle short/ because the ancient valor in Italians hearts/is not yet dead.” Then she extends the quotation to include the final words of Petrarch’s poem that Machiavelli did not include in The Prince: “Seek your fortune among those favorable to true peace. / Say to them: ‘Who will defend me? I go calling out: Peace. Peace. Peace.” Hull appears to be missing the rhetorical move that Machiavelli is making. Wrenching Petrarch’s quote out of context, Machiavelli has transformed it from a call for peace to one for war and for political leadership that understands the realities of power. For Machiavelli, peace and freedom are only possible if a prince and a city are willing to wage war in the most horrible of ways.[1]
Hartley’s essay pursues an entirely different approach from either Habib or Hull. He asks “How, then, can a society achieve liberty?” He offers what he sees to be Machiavelli’s answer: people of a free city have parochial utilitarian concerns about liberty to protect their property and to live with their families in security. Prosperity and security are what liberty means to the people of a city. Princes can rely on this as a means to power. The problem for Hartley is that Machiavelli’s support for liberty is a means to an end, not an end in-itself. By pursuing freedom for the people, a prince maximizes his own power, not the freedom and prosperity of others in a society. But, Hartley warns, princes easily can become corrupted and turn against liberty and the free society, thus making princes, for Hartley, foes to liberty. Here I briefly part ways with Hartley. In contrast to Hartley, I believe that Machiavelli has a substantive notion of political liberty as an end in itself that links together the actions of a prince and the existence of a free city. People are free because they participate in a free city, not just because their properties and families are secure, but because their participation in public life makes them free. As I argued in my essay, the substantive political liberty of a free city founded by a Machiavellian prince does not necessarily include a commitment to the personal liberties and prosperity of the individuals who live in that city.
[1] See Petrarch, The Canzoniere Poem 128. For an enlightening discussion of Machiavelli’s use of the Petrarch quote see Mikael Hörnqvist Machiavelli and Empire. Cambridge: Cambridge University Press, 2004. Pp.257-58.

Conversation Comments Machiavellian Definitions of Liberty

“Out of his surname they have coined an epithet for a knave, and out of his Christian name a synonym for the Devil.” Macaulay’s description of Machiavelli was witty but not unusual in 1825. But, as Ted Harpham notes in his essay, in the last half-century political philosophers have excavated the ruins and found a deeper Machiavelli, one more friendly to liberty than Macaulay’s knavish devil.
As the essays in this symposium have made marvelously clear, the underlying question is what is meant by the term “liberty.” Over the course of these four essays, there is an explosion of definitions of “liberty,” which would have pleased Machiavelli immensely. After all, with so many definitions on the table, surely at least one of them will fit the needs of the moment.
Elizabeth Hull zeros in on the definition of liberty that best exemplifies the point: “Liberty is an Unconquered Country.” As all three of my conversation partners correctly point out, Machiavelli gives much advice to rulers on how both to free a country from oppressors and to maintain it as a free country once so liberated. For the Prince or the Ruler of a Republic, this is indeed a type of liberty; having no other power above him, the ruler is free to do as he likes. Machiavelli stands at his shoulder helping him figure out how to maintain this freedom. If we think about this type of liberty, then Machiavelli is indeed a good friend to liberty, perhaps the best friend ever.
Note, however, what an odd notion of liberty this is. In a given society, who exactly is free? Every single person who is subordinate to the ruler lacks the liberty enjoyed by the ruler. The leader of a town does not have the same liberty as the leader of the country in which the town is located. Consider: if the city of Florence is in the region of Tuscany which is in the country of Italy, only one of those three places can have a leader who is free in this sense of liberty. Everyone else is in the position of a person living in a conquered territory.
It is important to remember that it was to these wannabe leaders of Florence or Tuscany or Italy that Machiavelli was writing. These prospective rulers did not have a Leo Strauss mining the depths to tell them what Machiavelli really meant. Instead, Machiavelli’s books were ready-made manuals for how to seize and maintain power. For centuries that is what everyone knew these books to be. 
All of this raises a familiar question in reverse. If the ends to which Machiavelli’s writings have been put are not good, then do the ends condemn the means? Not necessarily. If your country was being oppressed by cruel leaders or was threatened by an evil foreign power, you might well wish to be ruled by slightly less cruel and evil devotees of Machiavelli. But we should not confuse the potential usefulness of such leaders in times of stress with the idea that such leaders will bring, or are even likely to bring, liberty to a country once the source of stress has been removed.

Conversation Comments How Machiavelli Remembers the Ladies

I see many commonalities in our approaches to the question of Machiavelli’s support for liberty.  Edward Harpham and Khalil Habib cite the same sentence in The Princeabout the importance of free will in a universe ruled by fortune.  The desire to preserve some percentage of our ability to act freely echoes Erasmus’ argument to Luther that our actions may be bound by God’s will, but we contribute something, we have both Christian and Machiavellian “virtue.”
Harpham, Habib, and I note Machiavelli’s desire for checks on a ruler’s power.  While I come at it from The Prince, James Hartley notes that the Discourses’ argument that liberty means “not fearing for the honor of wives and that of children, not to be afraid for oneself” scants civil liberties.
I’d suggest that the demand that a prince “abstain” from the women of his subjects includes, more bluntly, freedom from rape.  That is a great liberty, a crucial negative liberty, however confined to relief from only one offender and linked to patriarchal ownership.  Habib’s sense that Mandragola represents sexual liberation makes that negative liberty more consequential.  In popular New Comedy the young couple conspire together, and medieval and renaissance erotic poets emphasize persuasion of the woman and value her free choice of the suitor.  It’s troubling that Mandragola’s woman is deliberately deceived in a plot among three men who fool her mother and husband into mercilessly pressuring her to commit adultery and, possibly, murder.  Only after she bows to the fraudulent badgering and has sex with her suitor, insisting, “I don’t want to” -- and only after her husband fondles the private parts of the young couple to verify penetration -- does the lover admit that he tricked her.   
Why, after this, not to put too fine a point on it, rape, does the lady agree to live with her deceiver?  Well, the lover is advised to “tell her” that “without scandal she can be your friend, and with great scandal, your enemy.”  He can tell the world and brand her an adulteress.  Ovid’s Tarquin made the same threat, and “overcome with fear of infamy, the dame gave way.”  The name of Ovid’s heroine?  Lucretia.  The name of Mandragola’s lady?  Lucretia.  Machiavelli chose his characters’ names with some care, and they matter.
His metaphor immediately before the demand to free Italia becomes all the more disturbing now:  “fortune is a woman; and it is necessary, if one wants to hold her down, to beat her and strike her down.”  Women are property and Fortuna can be made property.  Yet Machiavelli speaks admiringly of Caterina Sforza.  Caterina offered her children as hostages to her husband’s murderers, tricking them into giving her back her fortress’ keys.  Locking her captors out, she “threatened them with every kind of revenge.  And to show that she did not care for her children, she showed the enemy her genital parts, saying that she still had the mode for making more of them.”  
Caterina lived to fight the besiegers with her own two hands, to have two more husbands and two more children, and to survive her husband’s killer by two years.  Luck, be a lady, indeed.
Machiavelli, Niccolò.  Discourses on Livy.  Translated by Harvey C. Mansfield and Nathan Tarcov.  U Chicago Press, 1996/1998.
Machiavelli, Niccolò.  Mandragola.  Translated by Mera J. Flaumenhaft.  Waveland Press, 1981.
Machiavelli, Niccolò.  The Prince.  Translated by Harvey C. Mansfield, U Chicago Press, 1985/1998.
Ovid.  Fasti, Book II.  Translated by James George Frazier.  Harvard UP 1976.
Tylus, Jane.  “Theater and Its Social Uses:  Machiavelli’s Mandragola and the Spectacle of Infamy.” Renaissance Quarterly 53(3), 656-686.  

Conversation Comments Response

It was a pleasure to read these essays, and I was particularly struck by Hall’s insight into the importance of perspective in Machiavelli’s political thought.
Recall how in the dedicatory letter to The Prince, which he addressed to Lorenzo de Medici, Machiavelli states that the people can understand the prince and the prince the people. But this then raises the question of whether either the people or their rulers understand themselves. The problem that Machiavelli seems to be pointing to here is the problem of self-knowledge. Is Machiavelli’s philosophy contemplative, as it is for Plato and Aristotle, and therefore fundamentally concerned with self-knowledge, or is it rather politically effectual and fundamentally concerned with the founding of regimes?
Edward Harpham examines three important features of Machiavelli’s thought that help to draw out Machiavelli's understanding of liberty. In the Prince, for example, Machiavelli focuses on individual liberty: What can individuals do to control their own destiny? By contrast, in the Discourses, Machiavelli appears to be concerned with cultivating liberty in a people, and thus the Discourses is a more openly republican book than the Prince. Just as an individual is free provided he controls his own destiny, so too a city is free if she conducts her own domestic and international affairs independent of foreign influence. The practical problem is how to establish a civil religion, as ancient Rome did, that instills virtue in a people and that is conducive to self-government. 
Harpham identifies three important contributions that Machiavelli makes toward an understanding of political liberty. First, Machiavelli encourages us to assume that all individuals are wicked, and are prone to abuse power and dominate others. Second, religion requires rituals in order to form habits that are conducive to liberty. Often, however, a return to a religion’s austere beginnings is necessary in order to correct the people should their religious practices become corrupt. Third, Machiavelli simply assumes that class tensions are inevitable but may serve liberty provided proper institutions are in place to channel conflict into a system of checks and balances.
James Hartley focuses on the tenuous nature of liberty and the moral (or amoral) character of Machiavelli’s understanding of it. How can a city establish and maintain liberty? Great political effort is required if liberty is to be established. Indeed, an enlightened ruler is necessary in order to establish and maintain liberty. Establishing liberty, however, is difficult and is often in conflict with traditional morality. Consider for example Romulus, who founded Rome by first murdering his brother and then establishing institutions to maintain Rome's liberty. When Rome transitioned from a monarchy to a republic, the partisans of the old order, that is, the sons of Brutus, had to be murdered. And in the Prince, Machiavelli celebrates the vicious murder of Remirro de Orca, drawing the lesson that violence is often necessary for establishing law and order.
Hartley wonders: Is there a contradiction at the heart of Machiavelli's understanding of liberty? If liberty requires frequent illiberal measures, examples of which abound in Machiavelli’s writings, what then is the difference between liberty and tyranny? Machiavelli seems to have little to say about the content or character of liberty (at least in the Prince). Hartley draws our attention to one of the few explicit discussions of what Machiavelli means by liberty in the Prince, which amounts to abstaining from a citizen's property and spouse. For Hartley, Machiavelli’s impoverished, and perhaps even evil, notion of liberty is a consequence of Machiavelli reducing liberty to a means rather than to a moral end. According to Machiavelli, human beings are naturally acquisitive. Good government allows humans to acquire and maintain their possessions. This might constitute a lowering of the ends of politics in a way that not everyone will find to be satisfactory. Indeed, Hartley, like many others, sees Machiavelli as a serpent-like character who beguiles human beings with a vicious teaching that corrupts more than it serves human nature, to say nothing of liberty. We must bear in mind that liberty has traditionally been understood as a life governed by the practice of moral virtue and not license or the satisfaction of the passions.