A painting of a man

Machiavelli exposed the brutal truth about politics in a 'tell-all' treatise

After surviving years in the snake pit of Renaissance politics, Machiavelli penned 'The Prince,' his candid exploration of the mechanisms of power and leadership.

Santi di Tito’s portrait of Machiavelli was painted after the author’s death and hangs in the Palazzo Vecchio in Florence.

Life must have seemed good for Niccolò Machiavelli in late 1513. The former Florentine diplomat, who had built his reputation as a shrewd political analyst in his missions to popes and kings, was now at leisure on his farm near Florence. From there, Machiavelli wrote a letter to a friend on December 10 that year, describing his daily routine: He spent his mornings wandering his woods, his afternoons gambling in a local tavern. His evenings he spent in his study, where he composed “a little work”: De principatibus (On Principalities), on which he said, “I go as deeply as I can into considerations on this subject, debating what principalities are, how they are gained, how they are kept, why they are lost.”

Best known today as The Prince, this “little work” has had a mighty impact on history. With its most famous maxim—“It is better to be feared than loved”—the book explains not what rulers ought to do, but what they need to do to retain power. Considered an evil tract by many, modern philosophers now regard The Prince as the first modern work of political science.

Life, however, had not always been so restful or pleasant for Machiavelli as described in his letter. Only a few months before, he had found himself in mortal danger, on the sharp end of the power he so brilliantly analyzed. In 1512, the year before he wrote The Prince, the Florence administration he had served as a diplomat was overthrown by the Medici family, who had ruled Florence for much of the 15th century until their temporary overthrow in 1494. Machiavelli’s diplomatic career had evolved in the 18-year absence of the Medici. With their return to power, he lost his political position—and nearly his life. (The Medici family backed some of the Renaissance's most beautiful paintings.)

In February 1513 an anti-Medici conspiracy was uncovered, and Machiavelli’s association with the old regime placed him under suspicion. Historians believe he was not involved but was arrested anyway. Held in the Bargello prison, Machiavelli was tortured over a period of several weeks by means of the strappado, a device that dropped bound prisoners from a height in order to dislocate their shoulders and arms. Machiavelli maintained his innocence throughout this excruciating ordeal.

The timely appointment of Giovanni de’ Medici as pope in March 1513—together with Machiavelli’s pleas to the Medici in the form of witty sonnets—helped secure his release. Injured, unemployed, but alive, Machiavelli found himself convalescing on his farm and writing what would become his masterwork.

Magnificence and mayhem

Machiavelli was born in Florence in 1469, the son of a lawyer who had fallen on hard times. Nevertheless, the young Niccolò received a solid humanist education, learning Latin and some Greek. The Florence of his childhood was ruled by Lorenzo de’Medici, whose sobriquet “the magnificent” reflected not only his power and wealth but also his patronage of Renaissance luminaries such as Leonardo da Vinci, Michelangelo, and Sandro Botticelli.

Machiavelli was 24 at the fall of the Medici in 1494 and lived through the subsequent de facto rule of Florence by the ascetic Dominican friar Girolamo Savonarola. The new leader railed against church corruption embodied in the worldly Pope Alexander VI. Savonarola most famously carried out a citywide burning of luxuries, the “bonfire of the vanities.”

Long before he wielded direct power, the friar’s fiery edicts would have loomed over Machiavelli’s earlier years. Records show that Savonarola started preaching in Florence in 1482, when Machiavelli was 13, but the impact of these early sermons on the young man is unknown. The first mention of the friar in Machiavelli’s papers dates to March 1498, when he was nearly 30 years old. In a letter Machiavelli recalled how Savonarola could captivate an audience and noted how the friar “acts in accordance with the times and colors his lies accordingly.” Savonarola made an impression on Machiavelli, who later wrote of him in The Prince, calling him an “unarmed prophet.” While he admired the friar’s ability to adapt his message to the circumstances, Machiavelli later noted that while this skill might help one gain power, words alone were not enough to secure it: Force was necessary to keep a firm grip.

Savonarola was ousted in 1498; he was hanged and his body burned. A lack of biographical information has made it difficult to account for Machiavelli’s precise movements during the turmoil of these years. All historians know is that soon after Savonarola’s demise, Machiavelli, then age 29, emerged to become head of Florence’s second chancery. By the early 1500s he was effectively the foreign minister of the Florentine republic, serving the city’s chief minister, Piero Soderini. The post required extensive travel and first-class political and diplomatic skills. (Table manners as we know them were a Renaissance invention.)

Machiavelli was privileged to have lived in highly interesting, if chaotic, times. While Italian cities, Florence in particular, were nurturing the great flourishing of learning and culture of the Renaissance, the peninsula was, at the same time, the focal point of seemingly endless war, intrigue, and violence between Europe’s powers.

France’s self-destructive attempt to claim the Kingdom of Naples in the late 1400s attracted the emerging power of Spain and the old power of the Holy Roman Empire. All three were drawn deep into Italian affairs. In the confusing mosaic of Italian city-states, alliances continually shifted. Machiavelli gained a reputation for shrewdly interpreting the intentions of all contending powers and devising responses that would best serve Florentine interests.

One of his less successful diplomatic encounters was with the Countess of Forlì and Lady of Imola, Caterina Sforza, whom he met in 1499 in an attempt to secure her loyalty to Florence. The countess later reneged on a verbal agreement, making Machiavelli look somewhat foolish. He seems to have taken revenge by popularizing a sensational story about her reaction on learning, in a 1488 siege, that her children had been taken hostage: She stood on the ramparts, he wrote in The Prince, “and to prove to [her captors] that she cared not for her children, she pointed to her sexual parts, calling out to them that she had wherewith to have more children.”

The episode is probably apocryphal. Machiavelli resented Sforza, but the story also betrays a certain admiration. He may also have seen some irony in what happened next: In 1500, in part by forgoing the protection of Florence, Sforza lost the cities of Imola and Forlì to the man whom Machiavelli would one day make the model of his great work: Cesare Borgia.

Enter 'The Prince'

The illegitimate son of Pope Alexander VI, Borgia embodied the mix of sacred and earthly claims to power that marked Renaissance Italy. Appointed a cardinal by his father, Borgia’s true vocation was waging war and acquiring wealth. A brutal, ruthless, but often brilliant soldier, he had one obsessive aim: to carve out a state for himself and his clan in central Italy. He knew he could only do this under the formidable protection of his elderly papal father. And so, in a race against time, Borgia waged war through Romagna, driven by his motto: “Aut Caesar aut nihil—Either a Caesar or nothing.” (Leonardo da Vinci made this famous map for Cesare Borgia.)

Machiavelli first met Borgia at Urbino in summer 1502 to assess how much of a threat the pope’s son was to Florence. Observing Borgia and his methods informed Machiavelli’s emerging principal theories of power and politics. One event that would have a deep impact on Machiavelli’s ideas was the means by which Borgia reversed a period of bad fortune. Various Italian city-states had encouraged a revolt against Borgia. Realizing he was outnumbered, Borgia feigned reconciliation while cannily building up his forces. In late 1502 Borgia lured his rivals, the Orsini, to the town of Senigallia and had them strangled. Machiavelli carefully recorded the events in a 1503 dispatch.

Cesare Borgia’s luck ran out, however, after his father, the pope, died in 1503. His family fell from favor when the new pope, Julius II, removed the Borgias from power and exiled them to Spain. Cesare was imprisoned but managed to escape to Spain where he died in 1507. (Was Cesare Borgia's sister Lucrezia political pawn or predator?)

From prison to The Prince

Machiavelli’s fortunes did not change drastically at first. On behalf of Florence, he dealt with Pope Julius II in Rome, as he had with Alexander before him, but in 1511, a shift in alliances would wreak havoc on Machiavelli, despite being the consummate survivor. Julius had been pro-French, but he suddenly allied himself with Spain against France. The Florentines, who had close ties to the French, were vulnerable.

In 1512 Spanish troops enabled the exiled Medici to return to Florentine rule. This regime change resulted in Machiavelli being swept into jail and tortured. After his release, he retreated from public life to exile on his farm, where he began writing the work that defined his legacy.

By Christmas 1513 Machiavelli had completed The Prince. On the surface, its title, in Latin, De principatibus, seems to correspond to conventional classical theories of princely governance. Literature such as these were often called “mirrors for princes.” Condensing ideas from philosophers like St. Augustine and Plato, these works had existed since the early Middle Ages as “advice manuals” for rulers, exhorting ethical governing along the paths of virtue and righteousness.

Machiavelli’s book, however, contained a new and shocking thesis for its time. Written not in Latin, but Italian, The Prince exalts ruthlessness and centers on lessons learned from Borgia’s tactics. “Cesare Borgia was considered cruel; nonetheless, that cruelty united Romagna and brought it peace and stability,” he wrote. Previously, princely conduct guides had dwelled on how a ruler gains power through his or her right and legitimacy to rule. For Machiavelli, however, the gaining of power, however rightful or legitimate, is irrelevant if the ruler cannot then hold on to it. The ends would justify the means.

It is not love that conquers, Machiavelli wrote, but fear: “Love is a bond of obligation which [subjects] break whenever it suits them to do so; but fear holds them fast by a dread of punishment that never passes.” The two aims of any prince, Machiavelli argued, is to “maintain his state [i.e., power]” so as to be able to “seek honor and glory.” To achieve such goals, a prince must possess “virtue,” but of a kind that upends conventional, or Christian, notions of virtuous behavior.

Virtue, in the Machiavellian sense, is an ability to adapt. It is flexible rather than rigid and defined by the circumstances. In a given situation, will generosity strengthen the prince’s position? Or would cruelty serve him better? A possessor of Machiavellian “virtue” will know which one to deploy depending on the situation.

The quality of virtue will also allow a prince to adapt to another important Machiavellian concept, that of “fortune.” No ruler can stop fortune in full spate. Yet sometimes, fortune can be diverted, when a shrewd prince uses his vitue. During the revolt of the Orsini, Borgia had deployed his “virtue”—cunning and deceit—to turn the tide of his bad fortune.

Machiavelli's last act

After the completion of The Prince, Machiavelli dedicated it at first to Giuliano de’ Medici, son of Lorenzo the Magnificent. After Giuliano’s death in 1516, the book was dedicated to his successor, the Duke of Urbino Lorenzo de’Medici. Machiavelli spent the rest of his life working. He wrote a book on war and a reflection on the principles of republican rule. In later life he served Giulio de’Medici (a cousin of Giovanni and Giuliano), who in 1523 became Pope Clement VII.

Following Machiavelli’s death in 1527, however, it was his writing and not his service that would secure his place in history. The advice espoused in The Prince led his name to become shorthand for cunning, manipulation, and self-serving behavior—one of the few eponymous adjectives to strongly convey an abstract idea. His open appeal to guile and his subversion of Christian norms were regarded as so abhorrent that, in 1559, the work would be listed in the Catholic Church’s Index of Prohibited Books.

To others, the book was refreshingly honest, a survey of the reality of statecraft as it was actually practiced by rulers throughout history. Seventeenth-century philosophers such as Benedict Spinoza defended it. The radical 18th-century thinker Jean-Jacques Rousseau argued its author was “an honest man and a good citizen,” and that The Prince was an exposure, not a celebration, of the abuse of power. Today the book is foundational, a now classic treatise on governing, indispensable to the study of history and political science.

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