Niccolò Machiavelli and Ruthless Politics

Niccolò Machiavelli, a Florentine born in 1469, observed the brutal realities of power, shaping his pragmatic political theories. His seminal work, The Prince, offers a realistic guide to power, reflecting his life's turbulent experiences.
Niccolò Machiavelli

The term “Machiavellian” is laden with negative connotations. However, the man it refers to had an exceptional understanding of the mechanisms of power, aided by his negative experiences. Niccolò Machiavelli, often accused of being cynical, was a great observer of human nature and very honest in writing not about how power should be exercised, but about how it actually was.

Niccolò Machiavelli was born in Florence on May 3, 1469, the same year Lorenzo de’ Medici effectively became the ruler of the city. During his childhood and adolescence, Niccolò had the chance to observe how power was exercised and its consequences: he was nine years old when Giuliano, Lorenzo’s brother, was assassinated by the Pazzi family (an episode known as the Pazzi Conspiracy), and in the thirteen years that followed, he witnessed how the lord of Florence accumulated power and the resulting consequences, both good and bad.

He was the third child of a fairly well-known family, with modest economic power but sufficient to provide a good education for the children. Besides his teachers, Niccolò had access to his father’s personal library, rich in works of the great classics: the young man developed a special passion for ancient history, reading works by authors such as Cicero, Thucydides, Livy, Polybius, and Plutarch, among others. The first two, in particular, left a significant mark on Niccolò’s consciousness and thoughts: from them, he learned that the exercise of power often deviated from moral reasons such as loyalty or ethics.

In the Service of the Republic

In 1494, after finishing his studies, Niccolò entered public life as an official of the Republic of Florence. During those years, the city was in the hands of Girolamo Savonarola, a radical preacher with whom Machiavelli was very critical: precisely because of this aversion to the religious figure, during his early years, Niccolò did not hold any important positions. However, when Savonarola was declared a heretic and burned at the stake in 1498, the young Machiavelli’s fortune changed within a few days, and he was entrusted with one of the most important posts, that of the second chancellor, responsible for foreign policy and military matters.

Although Machiavelli always aspired to dedicate himself to politics, he did not have much luck as a chancellor, both because those with whom he made agreements often changed their minds, and because, in general, alliances were very volatile. His greatest success, in 1509, was to reconquer Pisa, a port of vital importance for the Republic of Florence, although it cost him ten years of effort and several failed alliances. Many of his failures are also explained, above all, by the fragmented nature of the Italian peninsula, where any agreement, however hard-won, could vanish from one day to the next.

On the other hand, the experiences collected during the fifteen years of public service served as the basis for Machiavelli to develop his political thought, reinforcing his convictions about the unscrupulousness of rulers. Two characters, in particular, made a great impression on him. Caterina Sforza, Duchess of Forlì, is described by Machiavelli as a ruthless woman who would do anything to retain power; it is possible that Niccolò harbored resentment towards her since Caterina had withdrawn the promised military support to Florence against Pisa, making Machiavelli a laughingstock. The second fundamental character for understanding the Florentine’s thoughts and works is Cesare Borgia, the son of Pope Alexander VI, who, thanks to his ambition and total lack of scruples, managed to create a fleeting and small duchy in Romagna.

Prison and Exile

Machiavelli’s political career was unexpectedly cut short in 1512 when the Florentine troops were defeated at Prato by a Spanish army under the orders of Pope Julius II. This defeat paved the way for the return of the Medici family to the lordship of Florence and the persecution of those who had conspired to exile them from the city in 1494. One of the people involved had in his possession a sheet on which several names were noted, including that of Machiavelli, who – despite not having participated in the conspiracy – was arrested and tortured. Fortunately for him, a few weeks later, Giovanni de’ Medici was elected Pope Leo X, and as a gesture of goodwill for the beginning of his pontificate, he proclaimed an amnesty.

Machiavelli was thus released from prison, but the suspicions about him did not dissipate – in fact, he would be arrested again in 1521 – and his political career was over. He retired to his home in San Casciano in Val di Pesa, near Florence, where he spent several years in isolation. At first, he certainly dedicated himself to farming and raising livestock, but in 1521 his fortunes began to improve: after being released from the second arrest, the Florentine wool guild tasked him with negotiating the release of some workers who had fallen into the hands of bandits. Machiavelli succeeded and played a portion of his reward in the lottery, winning 20,000 ducats, a sum that allowed him to live comfortably until the end of his days.

Despite his new and more comfortable life, Machiavelli’s literary output dates back precisely to his years of isolation. During this period, he devoted himself to writing, cultivating various genres and themes: politics, history, and even theater and poetry. Although he became famous for his political thought, he was a lover of the arts from a young age: he composed sonnets as a pastime and wrote several dramatic works.

The Prince and the Exercise of Power

In 1513, he began his most famous work, The Prince – originally titled De Principatibus, “On Principalities” – in which he poured the experiences he had lived during his years in politics. Although today it is one of the most famous political science treatises, at its time, it was not well received: it was published five years after its author’s death, in 1532. Shortly after, it was included in the Index of Prohibited Books by the church because of the contempt it showed for the ethics of power, and it was only during the Enlightenment that the text received some attention, albeit mostly negative: the famous phrase “the end justifies the means” is not by Machiavelli – although it is popularly attributed to him – but comes from a note made by Napoleon on his copy of The Prince.

The book was intended as a practical treatise on how to exercise power efficiently. To write it, Machiavelli was greatly inspired by the cunning Cesare Borgia, who, for the author, embodied the virtues a prince should possess: not necessarily positive or moral, but those that best ensure power. Contrary to what is often attributed to him, Machiavelli is not entirely indifferent to ethical issues: one of his greatest concerns is given by the famous dilemma about what is better for a ruler, to be loved or feared. The Florentine scholar argued that the ideal would be to be both, but if one must necessarily choose, “it is much safer for the prince to be feared than loved, when one of the two is lacking. Because, in general, it can be said of men that they are ungrateful, fickle, false and dissembling, cowardly in danger, and greedy for gain. And while you benefit them, they are all yours, offering you their blood, property, life, and children, when the need is far off; but when it approaches, they turn against you. And the prince who relies solely on their words, finding himself without other defense in time of need, falls to ruin.” The text reflects Machiavelli’s years as chancellor: according to him, his greatest mistakes were caused by trusting the words of others.

On the other hand, this does not mean that for Machiavelli, the cruelty of rulers was desirable, but rather that it should be used wisely: “I say that every prince must desire to be considered merciful and not cruel. However, he must be careful not to misuse this mercy. […] And yet the prince must be cautious in believing and acting on dangers, and not be afraid of his shadow. He must combine prudence and humanity so that too much confidence does not make him imprudent, and too much distrust does not make him intolerable.” Machiavelli reiterates that the ruler who gains power through cruel means, once he has achieved it, must change his ways to quickly win the favor of the governed, but without ever ceasing to be feared by potential enemies: “[…] Love is maintained by a bond of obligation which, because men are wretched creatures, is broken whenever their interests are at stake; but fear is strengthened by a dread of punishment which is always effective.”

The Final Years

Although Cesare Borgia had served as inspiration for writing his book, Machiavelli chose to dedicate The Prince to the Medici family to gain the favor of the rulers of Florence. The stratagem worked and earned him the favor of Cardinal Giulio de’ Medici, who was elected Pope Clement VII in 1523. In addition to some diplomatic commissions, he asked Machiavelli to write two works on the history of Florence: The Art of War, a historical-political treatise in the form of a dialogue emulating Plato’s work, and The Florentine Histories, a collection of eight books on the city’s history. The Pope also appointed him superintendent of

Abel de Medici

Storica National Geographic, June 23, 2020


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