Machiavelli: 'The Prince' — A Pioneer of Modern Political Thought Who Looked Power in the Eye

Conclusion First (Key Takeaways)

• A pioneer of political realism: Machiavelli was among the first to analyze politics not as a subordinate of theology or moral philosophy, but as an autonomous domain with its own logic. His methodology — starting not from "how people should behave" but from "how people actually behave" — laid the foundations of modern political science.
• Virtù (capacity) and Fortuna (fortune): To what extent can a leader's capacity resist uncontrollable fortune? This problem structure is the heart of Machiavelli's political theory and the prototype of modern crisis management and leadership studies.
• Machiavelli the republican: Read The Prince alone, and he looks like an advocate of tyranny. But in his major work, the Discourses on Livy, he argues that a republic of free citizens is the most stable form of government. Only by reading both works together does Machiavelli's full picture come into view.

Life and Historical Context

Niccolò Machiavelli was born on May 3, 1469, in the Republic of Florence. His father Bernardo was qualified as a lawyer but was listed in the public register of debtors — hardly affluent. He was known, however, as a lover of books. Machiavelli's lifelong appetite for reading originated in his father's library.

Bernardo's diary contains a fascinating entry. He compiled an index for Livy's Ab Urbe Condita (History of Rome from Its Foundation) and received a copy of part of the work from the publisher as payment. That his son Niccolò would one day write his own masterwork using that very same Livy as its source is an irony of history. Machiavelli received a classical Latin education but never attended university. He read deeply and independently in Cicero, Livy, Tacitus, and Polybius — the Roman historians and thinkers.

He lived in an era when the Italian peninsula was at the mercy of Europe's great powers. Florence, Venice, Milan, the Papal States, and the Kingdom of Naples — five powers locked in shifting alliances and betrayals — were thrown into turmoil when France's King Charles VIII invaded Italy in 1494. It was the beginning of the Italian Wars, which would last sixty-five years. The reality of small states being trampled by great powers — this was the experiential foundation that shaped Machiavelli's political thought.

In 1494, when the de facto rulers of Florence, the Medici family, were expelled, the Dominican friar Girolamo Savonarola established a theocratic regime. The "Bonfire of the Vanities" — the public burning of citizens' luxury goods, artworks, mirrors, and books in the central piazza — was its emblem. But in 1498, Savonarola was executed as a heretic by burning at the stake. Years later, Machiavelli drew a lesson from this episode: "All armed prophets have conquered, and unarmed prophets have been destroyed" (The Prince, Chapter 6). Ideals alone cannot defend a state. Here lies the starting point of Machiavelli's realism.

After Savonarola's execution, under the new republic, the twenty-nine-year-old Machiavelli was appointed Head of the Second Chancery of Florence (1498). For the next fourteen years, he was engaged in the practical work of diplomacy and military affairs.

The most decisive experience was his diplomatic mission to Cesare Borgia (1502–1503). Borgia, the illegitimate son of Pope Alexander VI, was conquering the Romagna region with calculated brutality and boldness. Machiavelli observed his statecraft at close quarters, and one event in particular left him shaken.

Borgia, seeking to pacify the conquered and turbulent Romagna, gave full authority to his lieutenant Remirro de Orco, who restored order by ruthless means. When popular hatred concentrated on Remirro, Borgia himself had him arrested. One morning in the piazza of Cesena, Remirro's body was found cut in two, displayed alongside a wooden block and a bloodied knife. Machiavelli recorded: "The brutality of the spectacle left the people at once satisfied and stupefied" (The Prince, Chapter 7). Let a subordinate do the dirty work, pin the blame on him, then appear as the "liberator." This cold-blooded stagecraft of power was performed before Machiavelli's own eyes.

Another formative experience was the creation of a citizen militia. Italian city-states of the time depended on mercenaries for their military needs, but mercenaries, fighting only for pay, lacked loyalty and were prone to desertion in crises. Machiavelli keenly felt this problem and organized Florence's own citizen militia (1506), leading it to the successful capture of Pisa in 1509. But in 1512, when the Spanish regular army attacked Prato in Florentine territory, the citizen militia collapsed almost instantly. The bitter gap between theory and reality — this experience, too, was inscribed in his thought.

That same year, the Medici returned to Florence with Spanish military backing, and the republic fell. Machiavelli lost his position. In early 1513, he was arrested on suspicion of involvement in an anti-Medici conspiracy. The torture he endured was the strappado — his arms bound behind his back, hoisted by a pulley, and dropped — six times. Despite the agony of dislocated shoulders, he continued to maintain his innocence.

After his release, Machiavelli withdrew to his small estate at Sant'Andrea in Percussina on the outskirts of Florence. It was in this double life described in the Vettori letter — farming and the tavern by day, dialogue with the ancients by night — that The Prince and the Discourses were written.

The Prince was furnished with a dedication to the Medici family — a desperate bid for political rehabilitation that was never realized. In his later years, the Medici commissioned him to write the Florentine Histories, and he achieved literary fame with La Mandragola, widely considered the finest comedy of the Italian Renaissance. But he never returned to the front line of politics.

On May 6, 1527, the Sack of Rome brought down the Medici regime, and the republic was restored in Florence. But in a cruel irony, Machiavelli was barred from office as a "Medici collaborator." He had served the republic, been exiled when the republic fell, and was excluded when the republic returned. Bearing this double irony, he died on June 21, 1527, at the age of fifty-eight.

Timeline

• 1469: Born in Florence
• 1494: French King Charles VIII invades Italy. The Medici are expelled; Savonarola rises
• 1498: Savonarola burned at the stake. Machiavelli appointed Head of the Second Chancery (age 29)
• 1500: First diplomatic mission to the French court
• 1502–1503: Diplomatic mission to Cesare Borgia. Witnesses the Remirro de Orco affair
• 1506: Leads the creation of the Florentine citizen militia
• 1509: Citizen militia captures Pisa
• 1512: Citizen militia routed at Prato. Medici return; Machiavelli dismissed
• 1513: Imprisoned, tortured (strappado, six times). After release, retires and writes The Prince
• 1513–1519: Writes the Discourses on Livy
• c. 1518: Writes the comedy La Mandragola
• 1520: The Art of War published
• 1525: Presents Florentine Histories to Pope Clement VII (a Medici)
• 1527: Sack of Rome. Florentine republic restored, but Machiavelli is denied office. Dies June 21 (age 58)

What Did Machiavelli Ask?

Before Machiavelli, political thought flowed in two broad currents.

One was the tradition, stretching back to ancient Greece, of envisioning the "ideal state." Plato's Republic and Aristotle's Politics are its exemplars. The other was the medieval Christian genre known as "mirrors for princes" — represented by Thomas Aquinas and Giles of Rome — which taught that rulers should govern according to Christian virtues: justice, mercy, generosity, and good faith. Both currents shared a common starting point: the question "How should politics be?"

Machiavelli overturned this premise at its root. In Chapter 15 of The Prince, he declares: "Many have imagined republics and principalities that have never been seen or known to exist. But there is such a distance between how one lives and how one ought to live that he who abandons what is done for what ought to be done learns his ruin rather than his preservation."

This is the principle of "the effectual truth of the thing" (verità effettuale della cosa). Think about politics not from ideals but from the actual behavior of human beings. Separate politics from theology and moral philosophy, and establish it as a domain of knowledge with its own logic. In short: the secularization of political thought.

Behind this shift lay the brutal lessons of fourteen years of diplomatic practice. Savonarola may have been morally right, but he perished for lack of arms. Cesare Borgia was morally reprehensible, but he brought order. Moral good and political success do not coincide. This recognition was Machiavelli's point of departure.

From it emerged a question that was simple and fundamental: By what mechanisms are power actually acquired and maintained?

Core Theories

1. "The Effectual Truth of the Thing" — The Methodology of Political Realism

To think about politics from empirical fact (how things are) rather than from norms (how things should be). This simple turn is the core of Machiavelli's methodological innovation. And this turn became the headwaters of the intellectual current that modern political science calls "political realism." The twentieth-century international politics of E. H. Carr (The Twenty Years' Crisis, 1939) and Hans Morgenthau (Politics Among Nations, 1948) are Machiavelli's direct descendants.

The starting point is an unflinching observation of human nature. "One can say this in general of men: they are ungrateful, fickle, pretenders and dissemblers, evaders of danger, eager for gain" (The Prince, Chapter 17). This is not an expression of misanthropy. It is a "working hypothesis" for the analysis of politics. If human beings were always virtuous, politics would need little sophistication. It is precisely because they oscillate between good and evil that governance demands the highest skill and judgment.

This methodology has clear limits. If one asks "What is effective for maintaining power?", the question "Is that power legitimate in the first place?" tends to be set aside. Rousseau put it sharply: "Machiavelli professed to teach kings; but it was the people he really taught. His Prince is the book of republicans" (The Social Contract, Book III, Chapter 6). Indeed, insofar as it "exposes" the mechanics of power, The Prince is simultaneously a manual for rulers and a warning for the ruled.

2. Virtù — Not Moral "Virtue" but Political "Capacity"

The most important — and most misunderstood — concept in reading Machiavelli is virtù. Etymologically derived from the Latin virtus (virtue, manliness), Machiavelli's use of the term is fundamentally different from the Christian moral virtues of justice, temperance, and mercy.

Virtù is the comprehensive capacity needed to respond to political situations. Decisiveness, agility, boldness, the readiness to exercise cruelty when necessary, and above all, the ability to adapt to changing circumstances.

Consider a concrete example: the Remirro de Orco affair. Borgia executed a three-stage political operation as a single continuous act. First, he had Remirro use brutal methods to suppress disorder. Then, when popular hatred focused on Remirro, he personally had him executed and appeared as the "liberator." Morally condemnable, but politically superb in its virtù — this was Machiavelli's assessment (The Prince, Chapter 7).

Yet virtù is not mere violence or cunning. In Chapter 8 of The Prince, Machiavelli discusses the Sicilian tyrant Agathocles. This man seized power through atrocious means, but Machiavelli's verdict is clear: "It cannot be called virtù to kill one's fellow citizens, betray one's friends, be without faith, without mercy, without religion." Such methods "can win a prince power but not glory." Virtù contains an aspiration toward excellence that transcends mere effectiveness.

Machiavelli writes: "He should not depart from the good if he can hold to it, but he should be ready to enter upon evil if he must" (Chapter 18). The practical judgment to deploy good and evil according to circumstances. Some scholars have noted a structural resemblance to Aristotle's phronēsis (practical wisdom) (Garver, 1987). But there is a decisive difference: the aim of phronēsis is always moral good, whereas virtù can sacrifice moral good for the political end of "preserving the state."

3. Fortuna — The Struggle Against Fortune

The counterpart to virtù is fortuna — fortune, chance, the tide of events. Machiavelli explains it with a vivid metaphor. Fortuna is like "a raging river" that, when in flood, sweeps everything before it. But if dikes and channels are built in calm times, the damage can be minimized (The Prince, Chapter 25).

His estimate is this: "Fortune is the arbiter of half of our actions, but she still leaves the other half, or close to it, for us to govern."

In ancient Rome, Fortuna was a capricious goddess. Medieval Christianity replaced her with divine Providence, placing all events within God's plan. The scope for human intervention in fate was narrow. Machiavelli liberated fortuna from theology and redefined it as "uncertainty that leaders must confront." The modern concept of crisis management has its prototype here.

But even the fullest exercise of virtù cannot guarantee victory. The case of Cesare Borgia proves it. Borgia took every precaution, but one thing he could not foresee: when his father, Pope Alexander VI, died, Borgia himself was gravely ill. At the most critical moment for consolidating his power, he was unable to act. Machiavelli concludes: "The only thing for which he can be blamed is this one point" and "I know of no better model to offer to a new prince" (Chapter 7).

Virtù does not guarantee success. Yet it remains the best effort that human beings can make. Herein lies the tragic undertone of Machiavelli's thought.

4. "Loved or Feared?" — The Emotional Foundations of Power

Perhaps the most famous of all Machiavelli's questions. The Prince, Chapter 17: "Is it better to be loved or to be feared?"

The answer: ideally, both. But the two are hard to combine. If one must choose, "it is much safer to be feared than loved."

Why? Return to the view of human nature outlined above. People are ungrateful. When their interests are no longer served, they drift away. Bonds forged by love are severed by self-interest, but bonds forged by fear persist through "dread of punishment."

However — and this caveat is often overlooked — Machiavelli strictly distinguishes "being feared" from "being hated." "A prince must above all avoid being hated" (same chapter). Do not confiscate citizens' property. Do not carry out arbitrary executions. Once this line is crossed, no amount of virtù can undo the damage.

This argument is repeatedly invoked in modern discussions. The "warmth and competence" two-axis model developed by Fiske, Cuddy, and Glick (2007) can be read as a translation of Machiavelli's question into the language of experimental psychology. That said, the extreme circumstances of sixteenth-century Italy, where the survival of states was at stake, should not be casually equated with modern corporate management.

5. Republicanism — Liberty and Civic Virtue

To judge Machiavelli by The Prince alone is one-sided. The work he himself considered more important was the far longer Discourses on Livy — formally, "Discourses on the First Ten Books of Titus Livius." Through an analysis of the ancient Roman Republic, it argues for the superiority of republican government.

The core argument is this: the virtù of a single individual has limits. But the collective virtù of free citizens can surpass those limits. "The many are wiser than the individual and make better choices" (Discourses, Book I, Chapter 58).

Particularly striking is Machiavelli's evaluation of conflict. He does not view clashes between nobles and commoners negatively. On the contrary, he declares: "It was the discord between the plebs and the Senate that made Rome free" (Book I, Chapter 4). The prevailing wisdom held that political stability depended on harmony. Machiavelli overturned this head-on. Conflict and struggle forge institutions and safeguard liberty — a distant anticipation of modern pluralist democracy.

How, then, do The Prince and the Discourses fit together? One influential interpretation runs as follows: in a thoroughly corrupt state, a "new prince" must first build the foundations of liberty and order from scratch. Upon that foundation, the ultimate goal is to establish a republic. In other words, The Prince is a treatise on the "emergency measures" needed to achieve the republican end.

In the latter half of the twentieth century, the research of J. G. A. Pocock (The Machiavellian Moment, 1975) and Quentin Skinner (Liberty before Liberalism, 1998) led to a major reassessment of this republican dimension. Today's civic republicanism regards Machiavelli as an important intellectual source. Nevertheless, his republicanism has its limits — the exclusion of women (virtù is etymologically linked to masculinity) and the endorsement of military expansion — and cannot be applied directly to the present day.

6. Necessità — The Logic of "Necessity" in Politics

Another key concept is necessità — "necessity" or "compulsion." When the survival of the state is at stake, the prince must be "compelled by necessity" to enter the domain of evil. "Necessity" here denotes a force of circumstances powerful enough to suspend ordinary moral standards temporarily.

This logic is the prototype of what contemporary political philosophy calls the "dirty hands" problem. Can a political leader be justified in committing morally condemnable acts for the public good? Michael Walzer's classic essay "Political Action: The Problem of Dirty Hands" (1973) analyzes precisely this question. The decision to drop the atomic bomb, the use of torture against terrorists, the sacrifice of civilians in wartime — when grappling with such extreme political judgments, Machiavelli's concept of necessità is unavoidable.

The danger of this logic is obvious. The justification "it was necessary" can be applied retroactively to almost any act. Machiavelli himself explicitly rejected gratuitous cruelty as "badly used" and defined "well used" cruelty as "cruelty committed once out of necessity and not repeated thereafter" (The Prince, Chapter 8). But how objectively that line can be drawn remains one of the most contested questions to this day.

Guide to Major Works

• Introductory: The Prince (Il Principe), various translations (e.g., Harvey Mansfield, University of Chicago Press, 1998; Tim Parks, Penguin Classics, 2009) — Machiavelli's most famous work. Just twenty-six chapters and around a hundred pages. The declaration of "the effectual truth of the thing" in Chapter 15 alone is worth reading.
• Intermediate: Discourses on Livy (Discorsi sopra la prima deca di Tito Livio), various translations (e.g., Harvey Mansfield & Nathan Tarcov, University of Chicago Press, 1996) — The major work in which Machiavelli develops his theory of republicanism through the history of ancient Rome. Three books. Only by reading this alongside The Prince does the full picture emerge.
• Intermediate: La Mandragola (The Mandrake), various translations — A comedy in which a young man uses wit and stratagem to seduce a married woman. The cold-eyed observation of humans driven by desire and hypocrisy is unmistakably the work of the author of The Prince. A window into Machiavelli's view of human nature from a different angle.
• Intermediate: The Art of War (Dell'arte della guerra), various translations — A dialogue criticizing mercenary armies and advocating citizen militias. Essential for understanding that Machiavelli's political thought was inseparable from military affairs.
• Advanced: Q. Skinner, Machiavelli: A Very Short Introduction, Oxford UP, 2000 (revised edition 2019) — A concise and widely used introduction, exemplifying the Cambridge School's method of reading texts in their historical intellectual context.

Major Criticisms and Debates

1. "Written with the finger of the Devil" — The critique of separating morality from politics: The most fundamental criticism of Machiavelli was directed at his separation of politics from morality. The English Cardinal Reginald Pole denounced The Prince as "written with the finger of the Devil," and in 1559 the Catholic Church placed The Prince and the Discourses on the Index of Forbidden Books. In Elizabethan England, Marlowe's plays featured "Machiavel" as a diabolical schemer, and Shakespeare's Richard III bears his shadow. It was in this period that "Machiavellian" became virtually synonymous with "evil."

2. The paradox of The Prince and the Discourses: One advocates a strong leader; the other advocates a republic. How to understand this tension has remained the central problem of Machiavelli scholarship. Hans Baron (1961) read Machiavelli as a republican within the framework of "civic humanism," arguing that The Prince was merely a prescription for emergencies. Leo Strauss (Thoughts on Machiavelli, 1958), by contrast, read him as a "teacher of evil" and located him at the source of modern moral decline. Forerunner of democracy or fount of nihilism — this opposition remains unresolved.

3. The "subversive" readings of Rousseau and Gramsci: In The Social Contract, Rousseau wrote that Machiavelli "professed to teach kings; but it was the people he really taught." By exposing the mechanisms of power, he gave the people the weapons to resist. In the twentieth century, Antonio Gramsci developed this reading in his Prison Notebooks, reinterpreting the "new prince" as the revolutionary party. That Gramsci, imprisoned under Mussolini's fascist regime, found inspiration in Machiavelli is no coincidence. To understand the structure of power is the first step toward resisting it.

Influence and Legacy

Precursors: The ancient Roman historians Livy, Tacitus, and Polybius' theory of constitutional cycles. Cicero's republican thought — Machiavelli was thoroughly versed in Cicero's moralism and consciously inverted it. The medieval "mirrors for princes" tradition — this was the direct target of his critique.

Influence on modern political philosophy: Jean Bodin's theory of sovereignty (1576) extended the idea of "state autonomy" into legal theory. Hobbes' "the state of nature is a war of all against all" (Leviathan, 1651) can be seen as a theoretical refinement of Machiavelli's view of human nature. Spinoza, in his Tractatus Politicus (1677), explicitly praised Machiavelli as "a most acute and prudent man" — an exceedingly rare instance of a contemporary philosopher publicly commending him.

The tradition of "reason of state": Machiavelli's thought was received in sixteenth- and seventeenth-century Europe as the concept of "reason of state" (ragion di stato). Giovanni Botero (The Reason of State, 1589) ostensibly criticized Machiavelli while substantively inheriting his problematic. Cardinal Richelieu's French foreign policy and Bismarck's Realpolitik belong to the same lineage.

The Atlantic republican tradition: Pocock's The Machiavellian Moment (1975) demonstrated that Machiavelli's republicanism flowed through England's Harrington (The Commonwealth of Oceana, 1656) into the thought of the American Founding Fathers — Jefferson and Adams. Behind the separation of powers in the U.S. Constitution lies the shadow of Machiavelli's idea that "liberty is maintained through conflict."

Beyond philosophy: The realist school of international relations (Morgenthau, Kissinger), leadership theory in management studies, strategic thinking in game theory — Machiavelli's influence extends far beyond the boundaries of philosophy.

Connections to the Present

Machiavelli's challenge has only grown sharper five hundred years on.

First, the problem of political realism. The tension between moral ideals and power politics in international affairs remains unresolved. The recurring attempts at redrawing borders by force, even in the twenty-first century, once again lay bare the gap between the international legal order and "the effectual truth of the thing." The security of a sovereign state cannot be ensured by moral legitimacy alone. This observation, made five hundred years ago, remains valid.

Second, the problem of leadership. In a crisis, leaders must make rapid decisions under incomplete information. The question that confronted national leaders during the COVID-19 pandemic was quintessentially Machiavellian: "being loved" (granting citizens freedom) versus "being feared" (imposing mandatory restrictions) — which approach would ultimately save more lives?

Third, the problem of appearance and reality. In Chapter 18 of The Prince, Machiavelli writes that a prince must "appear merciful, faithful, humane, honest, and religious," but must "be ready to act against those qualities when necessary." In the age of social media, the gap between a politician's image strategy and their actual policies has become more visible than ever. Machiavelli recognized, five centuries ago, that "political communication" is an essential component of power.

Fourth, the problem of civic virtue. In our era of political apathy that hollows out democracy, Machiavelli's call grows ever more urgent: liberty, once won, is not automatically sustained. It is preserved only through constant participation and struggle. This is the heart of the Discourses — and the most important warning for modern democracy.

Questions for the Reader

• If you were the leader of an organization, would it be justified to use morally questionable means to protect it? If "yes," where is the limit? Can Machiavelli's distinction between "well used" and "badly used" cruelty help you draw the line?
• Machiavelli drew lessons from history on the premise that "human nature does not change." Is this premise correct? If institutions and education can change human beings, which parts of Machiavelli's theory would need to be rewritten?
• Who, in your own life, is the "Savonarola" — morally right but lacking real-world power — and who is the "Borgia" — indifferent to means but delivering results? Is a third way, beyond either extreme, possible?

Bibliography

• Primary (Main Work): N. Machiavelli, The Prince (Il Principe), written 1513, published 1532 / English translation: Harvey Mansfield (University of Chicago Press, 2nd ed., 1998); Tim Parks (Penguin Classics, 2009)
• Primary (Main Work): N. Machiavelli, Discourses on Livy (Discorsi sopra la prima deca di Tito Livio), published 1531 / English translation: Harvey Mansfield & Nathan Tarcov (University of Chicago Press, 1996)
• Primary (Letters): N. Machiavelli, Machiavelli and His Friends: Their Personal Correspondence, ed. & trans. J. B. Atkinson & D. Sices (Northern Illinois UP, 1996) — The letter to Vettori of December 10, 1513, is a primary source of the first order for understanding the genesis of The Prince
• Secondary (Intellectual Context): Q. Skinner, Machiavelli: A Very Short Introduction, Oxford UP, 2000 (revised edition 2019) — A concise and widely used introduction, employing the Cambridge School's method
• Secondary (Republican Tradition): J. G. A. Pocock, The Machiavellian Moment: Florentine Political Thought and the Atlantic Republican Tradition, Princeton UP, 1975
• Secondary (Critical Reading): L. Strauss, Thoughts on Machiavelli, Free Press, 1958 — A provocative classic that reads Machiavelli as a "teacher of evil" and locates him at the origin of modernity
• Secondary (Biography): R. Black, Machiavelli, Routledge, 2013 — A detailed and up-to-date intellectual biography drawing on the latest archival research
• Web: Stanford Encyclopedia of Philosophy, "Niccolò Machiavelli" (Cary Nederman) — A comprehensive overview including the current state of scholarship