53 pages 1-hour read

Leonardo Da Vinci

Nonfiction | Biography | Adult | Published in 2017

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Chapters 21-27Chapter Summaries & Analyses

Chapter 21 Summary: “Saint Anne”

Leonardo’s Virgin and Child with Saint Anne began as a commission for the church of Santissima Annunziata around 1501. A widely admired cartoon featuring Anne, Mary, and the Christ child was displayed publicly, but Leonardo delayed completing the final painting. Over time, he developed various versions, including the surviving Burlington House cartoon, which replaced the lamb with a young Saint John. By 1503, he had begun the painting itself, which fused his anatomical, geological, and compositional studies. The finished work shows the young Jesus wrestling with a lamb as Mary attempts to restrain him, symbolizing his embrace of the Passion. Though meant for an altarpiece, Leonardo kept the painting with him for the rest of his life, making continual refinements. The painting exemplifies his pursuit of complex motion, emotion, and meaning—what many consider one of his most layered and ambitious masterpieces.

Chapter 22 Summary: “Paintings Lost and Found”

This chapter explores two of Leonardo’s most debated works: the lost Leda and the Swan and the rediscovered Salvator Mundi. Although Leonardo likely completed Leda, the original is lost; scholars study workshop copies and a preparatory drawing to infer its themes of sensuality, birth, and natural renewal. The painting is notable as Leonardo’s only overtly sexual work, yet it emphasizes fertility over eroticism. Salvator Mundi, in contrast, reemerged in 2011 and was authenticated through technical analysis, historical documentation, and stylistic features. The painting shows Christ holding a crystal orb and blessing the viewer, combining Leonardesque softness, psychological mystery, and optical illusions. However, its lack of scientific refraction in the orb raised questions. Whether oversight or artistic choice, the anomaly reveals Leonardo’s complex balance between scientific precision and symbolic expression.

Chapter 23 Summary: “Cesare Borgia”

In 1502, Leonardo entered the service of Cesare Borgia, a brutal and cunning warlord whose rise was backed by his father, Pope Alexander VI. Borgia sought to consolidate power across central Italy, and Leonardo was enlisted—possibly with Florence’s encouragement—as a military engineer. During his eight months in Borgia’s service, Leonardo conducted fortification inspections, drafted innovative maps like the one of Imola, and sketched both military designs and landscapes. His time overlapped with that of Niccolò Machiavelli, who admired Borgia’s ruthlessness and documented his exploits. Despite Borgia’s vicious tactics—including the public execution of his own deputy—Leonardo focused on his technical work, creating bridges, harbor plans, and devices like an odometer. Ultimately, disillusioned by the bloodshed, Leonardo left Borgia’s service in early 1503 and returned to Florence. His tenure with Borgia highlights the tension between his scientific passions and the violent contexts in which they were sometimes applied.

Chapter 24 Summary: “Hydraulic Engineer”

After gaining hydraulic expertise in Milan, Leonardo turned his attention to improving Florence’s water systems and military defenses. In 1503, he collaborated with Niccolò Machiavelli on an ambitious plan to divert the Arno River and cut off Pisa from its sea access—a nonviolent method to reclaim the city. Leonardo’s design included detailed calculations, labor estimates, and a dirt-removal machine. However, the project was mismanaged by a new engineer who altered Leonardo’s specifications. The river failed to divert, and the project collapsed. Despite this failure, Leonardo envisioned a navigable canal from Florence to the sea and later applied his hydraulic and engineering knowledge in Piombino, designing fortifications and swamp-draining systems—including a fantastical centrifugal pump using artificial whirlpools. Though his large-scale plans were often impractical or unrealized, they reflected a visionary blend of creativity, scientific understanding, and a willingness to fail in pursuit of innovation.

Chapter 25 Summary: “Michelangelo and the Lost Battles”

In 1503, Leonardo was commissioned to paint The Battle of Anghiari in Florence’s Council Hall—a grand mural depicting a Florentine military victory. A year later, Michelangelo was assigned the opposite wall for The Battle of Cascina. The resulting rivalry symbolized a clash of artistic philosophies: Leonardo’s smoky, dynamic sfumato versus Michelangelo’s sharply contoured, sculptural forms. Leonardo focused his mural on a chaotic struggle for a battle standard, drawing frenzied sketches of men and horses, yet failed to complete the piece due to technical problems and artistic perfectionism. Michelangelo also left his cartoon unfinished, though both works—through copies and preparatory studies—influenced a generation of Renaissance artists. The cartoon rivalry elevated the status of painters from craftsmen to stars. Though lost, the works were famously called the “school of the world,” shaping the High Renaissance and the careers of artists like Raphael and Cellini.

Chapter 26 Summary: “Return to Milan”

In 1506, Leonardo left Florence—leaving the Battle of Anghiari incomplete—for a return to Milan, using a legal dispute over Virgin of the Rocks as a pretext. His father had recently died, leaving Leonardo out of the will, and tensions with his many half-siblings furthered his desire to leave Florence. The French governor of Milan, Charles d’Amboise, and King Louis XII welcomed him warmly and helped shield him from Florentine demands to return. In Milan, Leonardo met and informally adopted Francesco Melzi, a noble youth who became his assistant, student, and eventual heir. Although briefly returning to Florence in 1507 for an inheritance battle, Leonardo spent most of his remaining years in Milan. There, he engaged in scientific, architectural, and theatrical pursuits, contributing to civic pageantry and engineering projects. Milan’s intellectual diversity and courtly indulgence made it Leonardo’s preferred home until his final years.

Chapter 27 Summary: “Anatomy, Round Two”

Between 1508 and 1513, Leonardo da Vinci resumed and intensified his anatomical studies, sparked by the dissection of a centenarian at the hospital of Santa Maria Nuova. Over five years, he performed more than 30 dissections and produced 240 detailed anatomical drawings alongside thousands of words of notes. He explored every major system of the body—from musculature and nerves to the heart and brain—using engineering techniques and artistic skill to document his findings. Notable breakthroughs included early descriptions of arteriosclerosis and the aortic valve’s spiral-flow closure. Leonardo also compared anatomy to machines and natural systems, using analogies to deepen understanding. Despite plans to publish, his anatomical work remained largely unknown until centuries later. The chapter emphasizes both his scientific genius and his failure to disseminate his findings, which limited his influence on the development of modern anatomy.

Chapters 21-27 Analysis

This stretch of the biography captures a phase of Leonardo’s life where artistic brilliance confronts external constraint. Isaacson frames these chapters not as a creative lull, but as a period of friction—between genius and circumstance, ambition and reality. Political upheaval, patron demands, and personal fatigue shape the rhythm of Leonardo’s work, prompting the reader to consider how much of a visionary’s legacy is determined not by inspiration but by environment.


Isaacson returns throughout these chapters to the theme of unfinished or lost works—not as evidence of failure, but as a defining aspect of Leonardo’s creative philosophy. The idea that an incomplete project can still have a lasting impact is exemplified in Benvenuto Cellini’s praise of the Battle of Anghiari and Michelangelo’s Battle of Cascina as the “school of the world” (503). Though the murals were never completed, their preparatory cartoons shaped an entire generation of Renaissance artists. Isaacson uses this example to suggest that the influence of a work lies not only in its finish but in its imaginative power. This perspective reinforces The Tension Between Vision and Completion as not merely a character flaw, but a testament to the scale of Leonardo’s vision and the constraints of his world.


That tension is further complicated by Leonardo’s personal ethics and the practical realities of his commissions. His time serving Cesare Borgia underscores the contradiction between his pacifist ideals and his work as a military engineer. “Save me from strife and battle, a most beastly madness” (458), Leonardo writes, offering a rare emotional glimpse into his discomfort with violence. Isaacson doesn’t try to resolve this contradiction. Instead, he presents it as emblematic of Leonardo’s larger struggle to reconcile inner values with external obligations. The complexity of this relationship invites readers to reflect on the compromises inherent in any artist’s professional life—especially one navigating power structures as volatile as the Renaissance courts.


In other cases, Isaacson highlights the surprising ways Leonardo subverts or transcends real-world constraints. In his discussion of Salvator Mundi, for instance, Isaacson notes that Leonardo likely understood how light would refract through the crystal orb but chose not to paint the optical distortion “[e]ither because he thought it would be a distraction […] or because he was subtly trying to impart a miraculous quality to Christ and his orb” (443). This interpretive ambiguity is central to Isaacson’s portrayal of Leonardo. Even in a painting governed by realism and optical science, Leonardo leaves space for mystery and symbolism. The moment speaks to The Integration of Art and Science as a Path to Truth—a truth that, in Leonardo’s hands, is not always literal, but layered and philosophical.


Isaacson also explores Leonardo’s enduring interest in anatomy, especially during his return to dissection in the early 1500s. These studies were physically grueling and emotionally taxing, as Leonardo himself acknowledges: “You may be deterred by the fear of living through the night hours in the company of quartered and flayed corpses” (527). Isaacson emphasizes the devotion behind this work, using Leonardo’s own words to illustrate the psychological and moral intensity of his process. This moment reinforces Curiosity as a Discipline and a Way of Life—not as a whimsical trait, but as a sustained, often difficult commitment to seeing the world more clearly.

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