Machiavelli's The Prince: Virtue, Fortune and the Real Cesare Borgia

Who Niccolò Machiavelli Was

Niccolò Machiavelli was born in Florence on May 3, 1469, and died on either June 21 or June 22, 1527, depending on the source. From June 1498 he served as a secretary to the Florentine Republic, first as Second Chancellor and later with duties tied to the chancery and the city militia. For fourteen years he carried out diplomatic missions on Florence’s behalf: at the French court, before Emperor Maximilian’s imperial curia, and in Italy’s main centers of power. In 1502 he was sent to Romagna to deal with Cesare Borgia, an experience that would later become central to The Prince. Between 1506 and 1512 he also oversaw Florence’s military reform, becoming chancellor of the Nine Officers of the Militia.

His career broke off abruptly in 1512, when Spanish and papal troops brought the Medici back to power and defeated the civic militia Machiavelli himself had organized. He was dismissed and sentenced to a year’s confinement; in February 1513 he was arrested and tortured on suspicion of involvement in a plot against the Medici. It was during this period of forced isolation, cut off from the public offices that had filled his life for fourteen years, that The Prince was born.

This same restless, faction-torn Florence had already produced one exile two centuries earlier: Dante Alighieri, whose banishment from the city runs through the Divine Comedy — a reminder that political exile shaped more than one landmark of Italian literature.

How The Prince Came to Be

Sources agree on the year of composition, 1513, but differ on the exact window:

Machiavelli didn’t call his work “The Prince”: in a letter to his friend Francesco Vettori dated December 10, 1513, he calls it “De Principatibus.” The text was originally dedicated to Giuliano de’ Medici; the dedication was later switched to Lorenzo de’ Medici the Younger, in 1516, who almost certainly never read the book addressed to him. The Prince remained a manuscript passed privately from hand to hand for nearly twenty years: it wasn’t printed until 1532, in Rome, by the printer Antonio Blado, five years after the author’s death.

It should be kept separate from Machiavelli’s other major political work, the Discourses on Livy, probably begun around 1514 or 1515 and finished in 1518 or 1519, also published posthumously, in 1531. Where The Prince focuses on the power of a single ruler, the Discourses lay out the principles of republican government, using a commentary on Livy’s history of Rome as the pretext.

The Book’s Structure, Chapter by Chapter

The Prince runs 26 chapters, grouped into thematic blocks. The first eleven (chapters I-XI) classify the types of states and how they’re acquired: hereditary, mixed, new, won with someone else’s weapons or with one’s own skill. Three chapters on armies follow, distinguishing mercenary, auxiliary, one’s own, and mixed troops. The closing chapters cover the qualities a prince needs, the political crisis facing Italy at the time, and the role of fortune, ending with an appeal to the Medici to free Italy from foreign armies.

Virtue and Fortune, the Ideas at the Book’s Core

Two concepts run through the entire treatise: virtue and fortune. For Machiavelli, virtue is the set of practical qualities that let a prince “maintain his state” and achieve great things: above all, the skill to vary one’s conduct according to circumstance, rather than sticking to one way of acting in every situation.

Fortune is the unpredictable share of events, the part a prince doesn’t control. In chapter 25, Machiavelli compares it to one of those rivers that, when they flood, submerge plains and knock down trees and buildings — a danger that can only be contained by taking precautions before the water rises. From this image follows the idea that fortune is better met head-on than with a passive, wait-and-see approach.

To back this up, Machiavelli invokes what he calls “effectual truth”: the principle that politics should be judged by how people actually behave.

Practical example: when Machiavelli describes Cesare Borgia’s actions in Romagna, he doesn’t measure them against a moral yardstick — he examines the method: how territory marked by feudal anarchy was brought back to order through determined conduct. That’s effectual truth applied to a real case: looking at what worked, not at what would have been desirable.

Cesare Borgia, the Model Prince

Machiavelli witnessed Cesare Borgia’s actions firsthand — the man known as Duke Valentino — during a 1502 diplomatic mission in Romagna. He wrote about it in an almost documentary account, the Description of the Method Used by Duke Valentino to Kill Vitellozzo Vitelli: a short text, free of personal commentary, built as an objective narration of events.

In The Prince, Borgia becomes the example of the qualities a new prince needs — someone seizing power he didn’t previously hold: his actions, in Machiavelli’s telling, proved it was possible to tame the instability of territory marked by feudal anarchy through ruthless determination.

Why “Machiavellian” Isn’t Machiavelli

In everyday use, “Machiavellian” describes someone who pursues their own ends through cunning and disloyalty, without scruple. It’s a label that spread in the centuries after the author’s death, not a term Machiavelli used to define his own thinking. A decisive moment in this history was an attack by the French writer Gentillet, who branded The Prince the “Alcoran of the Courtiers” — an accusation that shaped the book’s reputation for generations, often more than its actual pages ever did.

Separating the historical work from its later use as a byword for cynicism also helps read it for what it is: an attempt to describe power the way Machiavelli had watched it work up close, across years of diplomatic missions and then in the forced exclusion from that same world.