Episode 43: Machiavelli the Man

I Take History With My Coffee Podcast
Episode 43
Title: Machiavelli, the Man

“His intellect was elegant and abundant, his morals lax; he was marvelously acute in comprehension, but without his actions corresponding to his thought; he felt about politics as Italy felt: his aims were high, his ideas lofty, but here were energies misused, greatness corrupted, that for lack of means and hope lay in the mud like the Roman eagles in defeat…Thus was Machiavelli, and thus was Italy itself.”

Gino Capponi, The History of Florence, 1876

Welcome back to the I Take History With My Coffee podcast, where we explore history in the time it takes to drink a cup of coffee.


No sooner had Savonarola’s body been dumped into the Arno River than supporters of the executed friar were purged from the government of Florence.  From the Councils of the Ten and of the Eight down to the lowest positions, supporters of Savonarola had to give up their offices in favor of those who had opposed the friar or wished to harm him.  And the more openly they had professed this opposition, then the better.  

One of these officials was Alessandro Bracci or Braccesi. He was the head of the second chancery and was Florence’s envoy at the Papal court. He tried to temper the pope’s animosity while navigating the growing divisions within the Florentine government. A relatively unknown young man of 29 was tapped to replace him: Niccolo di Bernardo Machiavelli.

Niccolo Machiavelli was born on May 3, 1469, in Florence.  He was the third child and first son of  Bernardo di Niccolò Machiavelli and his wife, Bartolomea di Stefano Nelli.  Bernardo had earned a modest living as a lawyer but faced financial troubles and was declared insolvent, which legally barred him from practicing his profession.  Bernardo Machiavelli made ends meet quietly by offering discounted services to those in financial straits similar to his own. His primary source of income came from a small estate inherited seven miles south of Florence, though it provided little financial stability.  His fortunes slightly improved with an inheritance from an uncle, Totto Machiavelli, but Bernardo struggled to support his family.

The Machiavelli family's origins were not obscure, although they were not among the most influential in Florence. Originally from the Val di Pesa, they owned significant land there. They became respected middle-class citizens in Florence. They were listed among other noted families, such as the Barbadori and Soderini. Their prosperity as "popolani grassi" (rich commoners) relied more on family properties than trade.  Despite their prominence, only one member, Girolamo, made a mark in Florence's history, facing torture, exile, and death for opposing the existing oligarchic rule in the latter half of the 14th century.

Later in life, Niccolo Machiavelli would describe his life as such: "I learned to do without before I learned to enjoy."  

However, despite this austerity, Bernardo Machiavelli had a deep passion for the humanities. Bernardo's diary, from 1474 to 1487, reveals his dedicated study of classical texts, the foundation of Renaissance humanism. He borrowed works by Cicero and acquired Livy's History, a text that later influenced Machiavelli's political philosophy.

In the face of financial adversity, Bernardo ensured Machiavelli received an excellent humanist education. Machiavelli's formal schooling began at seven under Master Matteo for Latin studies. By twelve, he progressed to the teaching of Paolo da Ronciglione, a renowned humanist educator. Bernardo proudly noted Machiavelli's advancement in Latin composition, following the humanist tradition of imitating classical models.

Moreover, it is believed that Machiavelli completed his education at the University of Florence, where he received further classical training, notably from Marcello Adriani. Adriani, a prominent figure at the university, contributed significantly to Machiavelli's intellectual development before assuming high office.

Machiavelli, the individual, is revealed through various sources, notably his official letters, reports, dispatches, literary works, and private correspondence. Machiavelli's private correspondence offers a unique window into his personality. Renowned as a prolific letter-writer, his letters were said to reflect his spoken words so closely that reading them was akin to hearing him speak in person. This skill in correspondence likely contributed to the charm he held for individuals of higher social standing who may not have otherwise engaged with him.

In his letters, Machiavelli delved into topics ranging from scandal to politics, showcasing a broad spectrum of emotions and tones. From expressions of boredom and depression to moments of exhilaration and conviction, his letters exhibit a fluidity that reflects his multifaceted character. Machiavelli's correspondence reveals him as lyrical and ardent in one instance, foul-mouthed and off-hand in another, demonstrating his sensitivity, changeability, and self-consciousness.

While often accused of cynicism, Machiavelli's outlook is interpreted as rooted in a sincere belief in his own logic rather than true cynicism. He is characterized as a great idealist with a cold realism, embodying a dualism that challenges those analyzing his character. 

Machiavelli is depicted as a generous, loving, honest father devoted to his country and freedom. His behavior, though perceived as corrupt by some of his contemporaries, is seen as a reflection of his refusal to hide his true self, preferring to be thought worse than he actually is.

“I never believe what I say, or say what I believe,” he wrote to a friend.

It is suggested that Machiavelli's appointment to the second Chancery in 1498 may have been influenced by his background in humanism. Adriani, Machiavelli’s former professor at the University of Florence, became the first chancellor that year, and he likely recognized Machiavelli's talents in the humanities and rewarded him with the position during the restructuring of the chancery following the change in leadership. This patronage from Adriani, possibly aided by Machiavelli’s father’s connections with humanist circles, played a crucial role in launching Machiavelli's public career within the new anti-Savonarolan government.

Machiavelli's official role encompassed two primary responsibilities. Firstly, he oversaw the second chancery, established in 1437, which primarily handled correspondence related to the administration of Florence's territories. Additionally, as the head of this section, Machiavelli held a prominent position as one of the six secretaries to the first chancellor. In this capacity, he was tasked with assisting the Ten of War, the committee responsible for the republic's foreign and diplomatic affairs. This dual role meant that Machiavelli not only managed regular office duties but also could be called upon to travel abroad on behalf of the Ten, serving as a secretary to its ambassadors and aiding in compiling detailed reports on foreign matters.

In July 1500, Machiavelli received his first opportunity to participate in a diplomatic mission when he and Francesco della Casa were tasked with traveling to the court of Louis XII of France. This commission stemmed from Florence's struggles in the war against Pisa, which had rebelled in 1494 and successfully resisted attempts to subdue them. Florence sought to regain control of Pisa with French assistance, but the endeavor failed.

Machiavelli's instructions were to absolve Florence of blame for the failed undertaking while subtly implicating the French commander of incompetence or corruption. However, Louis XII was more interested in Florence's future reliability as an ally than in excuses for past failures. This dynamic characterized Machiavelli's interactions with Louis and his advisors throughout their stay at the French court.

The experience in France taught Machiavelli valuable lessons about the shortcomings of Florence's government and the diminishing influence of Italian city-states in the face of modern kingships. He observed the perception of Florence as weak and unreliable, leading him to advocate for decisive and proactive governance in his later writings.

Despite his recognition of the need for swift action, Machiavelli remained hopeful about the potential of Italian city-states to assert their independence, even as he witnessed their eventual subjugation to more considerable European powers like France, Germany, and Spain.

The mission concluded in December 1500.

In 1501, Machiavelli married Marietta di Luigi Corsini, a woman from a family of similar social status. The Corsinis were slightly wealthier than the Machiavellis, and their union was primarily a social arrangement, typical of the time, aimed at consolidating familial alliances rather than based on romantic love. Despite this, Niccolò and Marietta developed a strong friendship, and they eventually had five children together. Their relationship was characterized by mutual affection and respect, common in arranged marriages of the period, where the expectations of romantic love were not as prevalent.

During his frequent missions to foreign cities, Machiavelli often formed connections with unattached women, fostering reciprocated affection.  Italian attitudes towards relationships during this time were open-ended but only on the male end.  This single-minded approach to relationships also influenced Machiavelli's political philosophy, particularly his belief that in governance, there could be no equal partnerships; the ruler, akin to the senior partner in a relationship, enforced rules while acting in their own interest. This perspective reflects the prevailing attitudes towards power dynamics and hierarchy in both personal and political spheres during the early modern era.

During the two years, Machiavelli spent primarily in and around Florence, the Signoria grew concerned about the emergence of Cesare Borgia as a formidable military force near their borders. In April 1501, Borgia was granted the title of Duke of Romagna by his father, Pope Alexander VI. This began a series of bold military campaigns to expand his territory to match his new status. Borgia swiftly captured several cities and orchestrated rebellions against Florence in the Val di Chiana. His lightning coup in overtaking the duchy of Urbino solidified his growing power.

Machiavelli was tasked with a delicate mission: to negotiate with Borgia and assess his intentions. This assignment marked the start of a pivotal period in Machiavelli's diplomatic career, allowing him to observe contemporary statecraft firsthand and form his own judgments. Despite his initial admiration for Borgia's courage, grand designs, and decisive actions, Machiavelli began to doubt the Duke's overreliance on luck and hubris.

His reservations grew as Machiavelli continued to monitor Borgia's actions, particularly during the papal court crisis following Pope Alexander VI's death. He observed Borgia's misjudgments and noted his excessive confidence despite mounting challenges. Initially communicated confidentially, these observations later found their way into "The Prince." Machiavelli criticized Borgia for his poor choices and overreliance on luck. Thus, Machiavelli's final assessment of Borgia was unfavorable, portraying him as a figure whose rise and fall were dictated by fortune rather than skill or strategy.

Through two distinct missions, Machiavelli had the opportunity to closely observe and assess the character and leadership of Pope Julius II. The first occurred in 1506 when Machiavelli returned to the papal court to report on Julius's aggressive plan to reclaim territories like Perugia and Bologna. The second chance arose in 1510 during a new embassy to France, where Julius was planning a crusade to expel the invaders from Italy. This placed Florence in a delicate position, torn between loyalty to the pope and allegiance to their French allies.

Initially, Machiavelli was impressed by Julius's bold actions. However, as Julius embarked on a risky venture against France in 1510, Machiavelli's admiration, like with Cesare Borgia, turned to skepticism and concern. He doubted the pope's ability to succeed, especially given the resource disparity between his forces and the French.

Machiavelli's observations of Julius's leadership are reflected in "The Prince," where he acknowledges Julius's impetuous yet successful approach to governance. However, Machiavelli suggests that Julius's successes were more a product of favorable circumstances than prudent leadership. He concludes that if Julius had faced different times requiring caution, his recklessness would have led to his downfall.

Between his papal legation in 1506 and his return to France in 1510, Machiavelli embarked on another mission outside Italy, allowing him to assess Maximilian, the Holy Roman Emperor. The Florentine Signoria sent Machiavelli to investigate Maximilian's plan to march into Italy and be crowned at Rome, which would require a substantial subsidy from Florence. Despite initial confusion about Maximilian's intentions, the proposed expedition was ultimately called off by June of the following year.

Machiavelli's assessment of Maximilian is notably harsh, lacking the nuances present in his descriptions of other rulers like Cesare Borgia and Julius II. Throughout his time at the imperial court, Maximilian appeared to Machiavelli as a fundamentally inept ruler, lacking the essential qualities necessary for effective governance. Machiavelli observed Maximilian's tendency to be overly lax and credulous, easily influenced by varying opinions, and unable to make decisive decisions. This lack of firmness and clarity in leadership resulted in confusion and inefficiency, with nobody knowing what actions the emperor would take.

Besides diplomacy, the second concern of the Florentine chancery was war. Since Florence lacked a reliable army, it hired professional soldiers who fought under their own leaders. Florence provided pay and logistical support, including transport, food, and ammunition. Florentine commissaries, often influential citizens, accompanied these armies to assist them in the field and exert political control over them.

Working for the Council of Ten, Machiavelli played a crucial role in this system, acting as a go-between and eventually a de facto commissary. His reliability and energy impressed Piero Soderini, then head of the Florentine government.  Soderini had been elected gonfalonier for life to stabilize the Florentine territories.  This was an unprecedented move for a city that still firmly believed in its republican traditions.  Even the Medici had never suggested such a move.  Soderini increasingly relied on Machiavelli as his personal aide. Machiavelli's fascination with war led him to delve deeply into its theory and master its intricacies. He advocated for enrolling rural subjects in a militia, which he organized, and his meticulous attention to supply and strategy during the campaign against Pisa contributed significantly to Florence's victory.

These successes further fueled Machiavelli's interest in military affairs. After 1512, he dedicated as much attention to war in his writings as he did to politics. He even published a book on the subject, "The Art of War," during his lifetime. Machiavelli's proficiency in military matters led some to consider him more of a military expert than a political or constitutional theorist.

By 1510, Machiavelli had formed strong opinions about most of the statesmen he had encountered during his decade of missions abroad. However, Pope Julius II remained somewhat enigmatic to him. Machiavelli found Julius's declaration of war on France in 1510 to be dangerously reckless, considering it would likely lead to conflict detrimental to Florence. Yet, he couldn't help but hope that Julius's bold actions might ultimately benefit Italy. Despite his reservations, Machiavelli entertained the possibility that Julius could become Italy's savior rather than its scourge.

Despite Machiavelli's optimism, events unfolded unfavorably. As we covered in the last episode, Julius II formed the Holy League with Ferdinand of Spain in 1511, drastically altering the political landscape of Italy. This alliance brought Spanish military support against France, leading to the French retreat and subsequent Spanish aggression towards Florence. Having failed to support the pope against France, the city faced dire consequences. Spanish forces sacked Prato and forced Florence to capitulate, resulting in the return of the Medici family to power and the republic’s dissolution.

Machiavelli's personal downfall was swift and severe. At forty-three, he was stripped of his office and citizenship, fined a substantial sum, and banished from Florence, leaving his life in ruins. The situation worsened when, four months later, he became entangled in a plot to assassinate Giuliano de' Medici. Despite his innocence, Machiavelli surrendered himself to the authorities and was thrown into the notorious Bargello prison.

In the grim confines of his cell, Machiavelli endured the torment of torture. Though physically unimposing, Machiavelli bore the torture with remarkable fortitude, later reflecting on his endurance with pride. The experience left an indelible mark on him, influencing his political theory, which emphasized the role of fear and punishment in governance.

After two harrowing months in confinement, Machiavelli was released, only to return to his small country estate in despair. Amidst the serene beauty of the Tuscan landscape, Casa di Machiavelli, known as L'Albergaccio ("Bad Hotel"), was located in  Sant'Andrea in Percussina.

Machiavelli found refuge in this residence during his exile from Florence. In one of his renowned letters to Francesco Vettori, dated December 10, 1513, he vividly depicts his daily routine, characterized by diligent management of the farm during the day and evenings spent at the attached tavern, engaging in card games with the proprietor and the local butcher. 

 Yet, he yearned for the excitement and influence he once wielded in political circles. Despite his outward semblance of contentment, Machiavelli's heart longed to return to the world of power and intrigue, where he had once been a significant figure. 

"When I arrived home I would go straight to my study. At the door I would take off my day clothes, which were covered with mud and dust, and put on my court robes. Appropriately attired, I would enter the courts of the past, where I would be affectionately received and sit down to dine on the food to which I was born, which is mine alone. Here I am no longer too timid to ask questions and demand reasons for particular actions, and the voices of the past courteously answer me. For four long hours I feel no weariness and I forget all my troubles. I no longer fear poverty, or am dismayed at the prospect of death. I devote myself entirely to my conversations .... "

During these nocturnal hours, Machiavelli immersed himself in intellectual pursuits, dedicating his time to reading and composing what would become one of his most influential works, "The Prince.” 

In the next episode, we will examine Machiavelli’s political philosophy, represented by his two most important works on political theory: “The Prince” and “The Discourses on Livy.”

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