Book Notes: Pt 7: Leonardo, Macchiavelli, and The Prince (From Leonardo da Vinci by Walter Isaacson)

Reading Time: 11 minutes

Leonardo da Vinci by Walter Isaacson

PublisherSimon & Schuster

ISBN-13 : 978-1501139154

Rating: ⭐⭐⭐⭐⭐

Part 1 | Part 2 | Part 3Part 4 | Part 5Part 6 | Part 7


Introduction

  • The relationship between Leonardo da Vinci, Cesare Borgia, and Niccolò Machiavelli is a fascinating example of how three brilliant personalities intersected during the Italian Renaissance, each grappling with the complexities of power, art, and morality in their own unique way. 
  • Their connection was forged in the crucible of Borgia’s ruthless military campaigns, an experience that left a lasting impact on both Machiavelli’s political philosophy and, perhaps, Leonardo’s worldview.
  • Both Leonardo and Machiavelli recognized Borgia’s intelligence and effectiveness. They also seem to have been fascinated by his charisma and power, even if they grappled with the ethical implications of his actions in different ways. 
  • Leonardo’s more artistic and perhaps sensitive nature may have led him to withdraw from the brutality he witnessed. In contrast, Machiavelli, the political pragmatist, sought to analyze and understand the dynamics of power that Borgia so effectively, if brutally, embodied.

Cesare Borgia

  • Cesare Borgia was a ruthless warrior who became the subject of Machiavelli’s The Prince. He was the illegitimate son of the Spanish-Italian cardinal Rodrigo Borgia, soon to become Pope Alexander VI, and he was known for his cruelty, treachery, and hunger for power. 
    • He [Rodrigo Borgia, Pope Alexander VI ] was the first pope to recognize openly his illegitimate children—ten in all, including Cesare and Lucrezia, by multiple mistresses—and he was able to get Cesare a dispensation from his illegitimacy so he could hold church offices. (330, loc. 5053-5055)
    • He made Cesare the bishop of Pamplona at fifteen and a cardinal three years later, even though the son showed less than zero predilection for piety. (330, loc. 5055-5056)
  • Borgia was a ruthless leader, known for violence, treachery, and corruption. 
    • Name any odious activity and Borgia was the master of it: murder, treachery, incest, debauchery, wanton cruelty, betrayal, and corruption. (330, loc. 5046-5047)
    • He had a brutal tyrant’s hunger for power combined with a sociopath’s thirst for blood. (330, loc. 5047-5047)
    • Once, when he felt he had been libeled, he had the offender’s tongue cut out, his right hand chopped off, and the hand with the tongue attached to its little finger hung from a church window. (330, loc. 5047-5049)
    • Preferring to be a ruler rather than a religious figure, Cesare became the first person in history to fully resign from the cardinalate, and he likely had his brother stabbed to death and thrown into the Tiber so that he could replace him as the commander of the papal forces. (330, loc. 5056-5058) 
    • His only sliver of historical redemption, which is undeserved, came when Machiavelli used him as a model of cunning in The Prince and taught that his ruthlessness was a tool for power. (330, loc. 5049-5050) 

Leonardo da Vinci

  • Leonardo da Vinci, while celebrated for his artistic genius, harbored a lifelong fascination with engineering and military matters. 
  • His decision to work for Borgia likely stemmed from a combination of pragmatism, a desire for patronage, and a genuine interest in military engineering. 
  • Leonardo, perhaps more sensitive to violence than Machiavelli, was deeply troubled by Borgia’s brutality.  Although he makes little mention of Borgia in his notebooks, he seemed to withdraw mentally from the horrors he witnessed, focusing instead on his engineering work, such as creating innovative maps for Borgia’s campaigns. 
  • Leonardo left Borgia’s service in 1503 after the warlord executed a group of leaders in Senigallia, one of whom was a friend of Leonardo’s.

The Meeting of Leonardo and Borgia

  • Leonardo first met Cesare Borgia in Milan in 1499 when Borgia was marching with King Louis XII of France. Borgia was a cardinal and commander of the papal armies at the time. 
  • Leonardo and Borgia likely met after Borgia and King Louis XII marched into Milan and visited Leonardo’s The Last Supper.
    • In that capacity, he [Cesare Borgia] forged an alliance with the French, and he was with King Louis XII marching into Milan in 1499. The day after their arrival, they went to see The Last Supper, and there Borgia first met Leonardo. (330, loc. 5058-5060)

Niccolò Machiavelli

  • Niccolò Machiavelli was a Florentine diplomat and writer known for his sharp observations and insights into power dynamics. 
  • At the time that he met Leonardo, he was a civil servant and secretary of Florence’s chancery, but was not yet the famous author of The Prince.
    • He shared with Leonardo the trait of being a sharp observer. (331, loc. 5074-5074)
    • He was not yet a famous author, but already he was known for his ability to produce lucid reports informed by insights into power balances, tactics, and personal motivations. He became a valued civil servant and secretary of Florence’s chancery. (331, loc. 5074-5076)
  • Machiavelli was sent to negotiate with Cesare Borgia as the warlord threatened Florence, and was present during Leonardo’s time in Borgia’s service, even sharing quarters with Leonardo and Borgia for three months in the winter of 1502-1503 in the fortified town of Imola.
  • Machiavelli’s time with Borgia would prove to be deeply formative, providing him with firsthand insights into the nature of power that would shape his most famous work, The Prince.

Leonardo in the Service of Borgia

  • In 1502, Borgia, on a campaign to carve out his own principality, demanded that Florence send a delegation to hear his demands. Florence, fearing an attack, sent Francesco Soderini and Machiavelli to negotiate with him. 
    • The elder was Francesco Soderini, a wily Church leader who led one of the anti-Medici factions in Florence. Accompanying him was the son of a bankrupt lawyer, well-educated but poor, whose writing skills and savvy understanding of power games had established him as Florence’s cleverest young diplomat: Niccolò Machiavelli. (331, loc. 5070-5073) 
  • As part of the agreement they reached with Borgia, Florence sent Leonardo to join Borgia’s service. Thus, Leonardo went to work for Cesare Borgia as a military engineer in 1502, likely as a gesture of goodwill between Borgia and the leaders of Florence. 
    • Once again a vague accommodation seems to have been reached, and Borgia did not attack. A few days later, probably as part of his arrangement with Florence that Machiavelli had helped to negotiate, Borgia secured the services of the city’s most famous artist and engineer, Leonardo da Vinci. (332, loc. 5081-5083) 
  • Leonardo’s motivations for joining Borgia are unclear. It is possible that he went as a gesture of goodwill or as a Florentine agent embedded with Borgia’s forces, but he may also have been genuinely interested in working as a military engineer for Borgia.
    • But either way, Leonardo was no mere pawn or agent. He would not have gone to work for Borgia unless he wanted to. (332, loc. 5087-5088) 
    • Borgia’s passport described Leonardo as he had fancied himself ever since his letter to the Duke of Milan twenty years earlier: as a military engineer and innovator rather than a painter. (334, loc. 5121-5123) 
    • He had been warmly embraced, in fulsome and familial terms, by the most vibrant warrior of the age. (335, loc. 5123-5123 

Possible motivations for Leonardo taking the job with Borgia:

  • A potential mission from Florence to act as an embedded agent in Borgia’s forces.
  • Leonardo’s interest in military engineering.
  • Leonardo’s possible fascination with powerful leaders.
  • Leonardo’s potential weariness with painting.

Leonardo’s activities during his time with Borgia’s armies

  • Leonardo spent eight months traveling with Borgia’s armies, traveling from Urbino to Imola to Senigallia. 
  • During this time, Leonardo created innovative and accurate maps for Borgia’s military campaigns, including a famous map of Imola. 
  • Leonardo’s map of Imola, considered a significant contribution to the art of war, features an aerial view, unlike most maps of that era, and combines artistry and military practicality.
    • While he was in Imola with Machiavelli and Borgia, Leonardo made what may be his greatest contribution to the art of war. (337, loc. 5163-5164)
    • is a map of Imola, but not any ordinary map. It is a work of beauty, innovative style, and military utility. It combines, in his inimitable manner, art and science. (337, loc. 5164-5166)
    • the Imola map was an innovative step in cartography. The aerial view is from directly overhead, unlike most maps of the time. (338, loc. 5170-5170)
    • On the edges he has specified the distances to nearby towns, useful information for military campaigns, but written in his elegant mirror script, indicating that the version that survives is a copy he made for himself rather than Borgia. (338, loc. 5170-5172)
    • The Imola map and others Leonardo made at the time would have been of great use to Borgia, whose victories came from conducting lightning strikes (338, loc. 5180-5181)
    • Acting as an artist-engineer, Leonardo had devised a new military weapon: accurate, detailed, and easily read maps. (338, loc. 5182-5182)
    • Over the years, visually clear maps would become a key component of warfare. (338, loc. 5182-5183)
    • In a larger sense, Leonardo’s maps are another example of one of his greatest, though underappreciated, innovations: devising new methods for the visual display of information. (339, loc. 5187-5189)
  • He also developed tools such as an odometer to measure long distances.
    • Around this time, he perfected the odometer he had been developing to measure long distances (338, loc. 5175-5175)

3 Months in Imola

  • Machiavelli also spent time with Borgia’s army during this period. While Leonardo was in Imola, Machiavelli was also there as an emissary and informant for Florence. 
  • For three months during the winter of 1502–3, Leonardo, Machiavelli, and Borgia were all together in the fortified town of Imola.
    • As the fall of 1502 approached, Borgia moved his court to the highly fortified town of Imola, thirty miles inland from Cesena on the road to Bologna. (336, loc. 5152-5153) 
    • Borgia’s plan was to turn the town into his permanent military headquarters by having Leonardo make it even more impregnable. (337, loc. 5156-5156)
    • Machiavelli arrived on October 7, sent by Florence to be an emissary and informant. (337, loc. 5157-5158)
    • For three months during the winter of 1502–3, as if in a historical fantasy movie, three of the most fascinating figures of the Renaissance—a brutal and power-crazed son of a pope, a sly and amoral writer-diplomat, and a dazzling painter yearning to be an engineer—were holed up in a tiny fortified walled town that was approximately five blocks wide and eight blocks long. (337, loc. 5160-5163) 

The Sack of Senigallia and Leonardo’s Departure

  • Leonardo left Borgia’s service shortly after the brutal sacking of Senigallia, in which several local leaders, including his friend Vitellozzo Vitelli, were executed on Borgia’s orders. Vitelli was strangled to death. 
  • Leonardo left Borgia’s service and returned to Florence in March 1503 shortly after this incident. 
    • Borgia then marched on the coastal town of Senigallia, where local leaders had rebelled against his occupation. He offered them a meeting to negotiate a reconciliation, and he promised that they could keep their leadership roles if they pledged to be loyal. They agreed. But when Borgia arrived, he had the men seized and strangled to death, then ordered that the town be pillaged. (340, loc. 5203-5205)
    • One of the strangled men was a friend of Leonardo, Vitellozzo Vitelli, who had lent him a book by Archimedes.(340, loc. 5207-5208)
    • A few days later, shortly after Machiavelli had been recalled to Florence, Leonardo left Borgia’s service. (340, loc. 5211-5212)

Leonardo’s Attraction to Power

  • It appears that Leonardo and Machiavelli got along well. They spent time together both in Florence and in Imola, and Machiavelli witnessed a contract for Leonardo in 1504.
  • Leonardo’s relationships with both Borgia and Machiavelli reflect his pragmatism in navigating the complex political landscape of Renaissance Italy. He was pragmatic and might have avoided commenting on Borgia’s actions out of a desire to maintain a good relationship with his patron and to avoid conflict with a brutal tyrant.
    • Partly this choice reflects Leonardo’s pragmatism. In a land where the Medici, Sforzas, and Borgias jostled for power, Leonardo was able to time his patronage affiliations well and know when to move on. (341, loc. 5215-5216)
  • However, Leonardo’s fascination with power and his desire to be a military engineer also likely played a role in his decision to join Borgia’s service.
    • But there is more. Even as he remained aloof from most current events, he seemed to be attracted to power. (341, loc. 5216-5217)
    • A simpler explanation is that Leonardo, who had just turned fifty, had dreamed for more than two decades of being a military engineer. (341, loc. 5219-5220)
    • As Isabella d’Este’s agent reported, he was tired of painting. Borgia had just turned twenty-six. He combined bravado and elegance.(341, loc. 5220-5221)
    • Indifferent to the shifting political agendas of Italy yet attracted to military engineering and strongmen, Leonardo had a chance to live out his military fantasies, which he did until he realized they could become nightmares. (341, loc. 5223-5224)

Contrasting Perspectives: Leonardo and Machiavelli

  • Both Leonardo da Vinci and Niccolò Machiavelli were firsthand witnesses to Cesare Borgia’s brilliant, but brutal, rise to power. 
  • The two men, both keen observers of human nature, processed their experiences with the infamous warlord in very different ways.
  • Leonardo’s notebooks are remarkably silent on the horrors he witnessed. Machiavelli, however, would use Borgia’s example as the titular model of cunning and to explore the nature of power in The Prince.
  • While Machiavelli transformed his observations of Borgia into a treatise on the acquisition and maintenance of power, The Prince, Leonardo turned inward, to his notebooks, and to his work, perhaps even seeking solace in his lifelong study of nature and artistic pursuits.

Leonardo

  • Leonardo’s notebooks from this period are largely devoid of comments on Borgia or the violence he witnessed.  It is possible that he used mental detachment as a coping mechanism. Leonardo might also have feared repercussions for criticizing Borgia, a powerful and ruthless leader.
    • his notebooks suggest that he had mentally tuned out Borgia’s horrors by focusing on other matters. (340, loc. 5208-5209)
    • “Save me from strife and battle, a most beastly madness,” Leonardo once wrote. Yet for eight months he had put himself at Borgia’s service and traveled with his armies. (340, loc. 5213-5214)
  • Leonardo’s relative silence on Borgia might point to a deep aversion to the violence he witnessed. 
    • He had intense, conflicted feelings about war. ( 350, loc. 5355-5355)
    • At one point in his notebooks he called war “a most beastly madness,” and some of his parables espouse pacifist sentiments. On the other hand, he had always been captivated and even beguiled by the martial arts. (350, loc. 5356-5358)
  • In preparing for his (never-to-be completed) mural, The Battle of Anghiari, Leonardo demonstrates the darker side of his nature:
    • Just the thought of war brought out Leonardo’s dark side and transformed the gentle artist. “There must not be a level spot that is not trampled and saturated with blood,” he concluded. (352, loc. 5392-5393 
    • he planned to convey the enthralling passion that made war so gripping as well as the brutality that made it so abhorrent. (350, loc. 5358-5359)
  • Thus, while working for Borgia, Leonardo, despite his stated desire to be a military engineer, seemed to “mentally tune” out Borgia’s horrors by focusing on other things, such as mapmaking and engineering projects. 
  • Despite Leonardo’s fascination with strongmen, his time with Borgia may have ultimately reinforced his aversion to violence and brutality. After leaving Borgia, he would eventually find a more suitable patron in the young, intellectually curious, and civilized King Francis I of France. 
  • Leonardo spent the last three years of his life in France, enjoying a generous stipend from the king and freedom to pursue his interests without pressure to produce artwork.

Machiavelli

  • In stark contrast to Leonardo’s relative silence, Machiavelli’s The Prince uses Cesare Borgia as a model for his exploration of power. 
  • The book, based on Machiavelli’s own experiences and observations of rulers like Borgia, provides a pragmatic, and often ruthless, guide to acquiring and maintaining political power. 
  • Machiavelli’s central argument is that a ruler must be willing to use any means necessary, including deception, violence, and even cruelty, to achieve his goals. 
  • In Borgia, Machiavelli saw a leader who embodied these principles, effectively using ruthlessness to consolidate his power in the Romagna region.
  • While Machiavelli admired Borgia’s intelligence and effectiveness, there is little to no evidence to suggest that he condoned Borgia’s cruelty. Rather, he seems to have viewed it as a necessary, albeit unpleasant, aspect of leadership in a treacherous political landscape.

Conclusion 

  • Borgia’s actions had a profound and lasting impact on Machiavelli’s political thought, as evidenced in The Prince. Machiavelli uses Borgia as a prime example of a ruler who, while ruthless, was also effective in securing and consolidating power. 
  • Machiavelli argues that in a world where morality is often secondary to political expediency, a ruler must be willing to employ any means necessary, including deception, violence, and cruelty, to achieve his goals. 
  • While there’s no evidence that Machiavelli condoned Borgia’s cruelty, he recognized that it was a tool Borgia wielded effectively in his pursuit of power.
  • Meanwhile, Leonardo, while fascinated by powerful figures and weaponry, expressed a distaste for “strife and battle”. 
  • Leonardo’s later years, spent under the patronage of the relatively enlightened King Francis I of France, suggest a desire to distance himself from the brutal realities of power politics and to focus instead on his intellectual and artistic pursuits.
  • In conclusion, the relationship between Leonardo, Borgia, and Machiavelli offers a glimpse into the complexities of the Italian Renaissance, a time of great artistic and intellectual flourishing but also of intense political intrigue and violence. 
  • While Machiavelli found in Borgia a model for his exploration of power, Leonardo seems to have turned inward, seeking refuge in his art and his scientific studies. 
  • It is a reminder that even the most brilliant minds can respond to the same experiences in vastly different ways.

Read the whole series

Part 1: Book Summary 
Part 2: The Outsider Who Revolutionized Art and Science
Part 3: Key Elements of Leonardo’s Genius and Actionable Insights
Part 4: The Interplay of Art and Science in Leonardo’s Work
Part 5: Technology and Culture as Catalysts for Genius and “Scenius”
Part 6: Leonardo da Vinci’s Note-Taking
Part 7: Leonardo, Macchiavelli, and The Prince