The Lost Battles: The Great Colliding of Leonardo Da Vinci and Michelangelo

It is undebatable that Leonardo da Vinci (1452 - 1519) and Michelangelo Buonarroti (1475 - 1564) are two of the greatest artistic personalities of the Italian Renaissance. In the course of the 15th and 16th century they created a series of masterpieces that have forever altered the history of art, shaping the way artistic expression is received and forged, and positioning themselves as some of the brightest and most extraordinary examples of craftmanship. Their unquestionable talent has left an indelible trace in human history to this day as they have often been considered to exemplify the apogee of Modern Art.

One of the most remarkable and interesting aspects of these two figures, however, is the fact that, as they were formed in the same city, Florence, and had a mere twenty-three years gap in age, their lives, as records show, inevitably intertwined. And, when in 1503 and 1504, both of them were assigned to paint the two main walls of the Great Council Hall of Palazzo Vecchio in Florence, so did their artistic path.

This article is a window into the reasons and results of this forced cooperation between two equally grandiose yet strikingly diverse personalities, and how significant this encounter has been to the history of art.

View of Florence known as Pianta della Catena, 1470. 1887.

In 1503 the city of Florence was in the midst of a great political change, as it was, for the first time in decades, ruled by a newly-instituted Great Council, an assembly of citizens, headed by Pier Soderini (1450 - 1522) and his counsellor Niccolò Machiavelli (1469 - 1527). After the expulsion of the Medici family in 1494 the city, in need of a guiding force, fell under the influence of the religious preacher Gerolamo Savonarola (1452 - 1498). He, at this time, had already gathered a considerable crowd of followers, after spending years harshly criticizing what he deemed to be a corrupt, money-greedy administration and preaching for a return to a pious, god-fearing way of life and ruling. Savonarola's power was such that when Florence eventually returned to an authentic republican structure, every effective political decision had to receive his approval, including the choice to constitute the Great Council, formed with representatives of people who, at that point, had little to no experience in governing a city as influential and florishing as Florence. As it often happens, Savonarola’s preaching became too extreme and radical for the new government and in 1498 he was publicly executed and his remains scattered in the Arno. This left the city in a deeply unstable condition, and the Great Council, being a new, moderate structure following both the glamorous Medici court and the religious charisma of Savonarola, needed to find ways to consolidate their ruling right in the eyes of the people. They required a way to present their political structure as the ultimate glorious manifestation of the pure liberty Florence was designed to embody. It is in this complex and fickle context that Pier Soderini chose to have the newly-built Great Council Hall of the Palazzo Vecchio painted by the two most notable Florentine names of the time: Leonardo Da Vinci and Michelangelo Buonarroti.

The Great Council Hall or Salone dei Cinquecento as it appears nowadays.

The walls of the Great Council Hall, a room of highly symbolical importance as the location of the ruling class’ assembles, were to be painted with murals of two emblematic episodes fully manifesting the strength of Florence: the Battle of Anghiari and the Battle of Cascina.

Leonardo was, at the time he was handed this assignment, at the acme of his fame, as his new piece of art, the portrait of Lisa Gherardini, now widely known as the Gioconda or the Monna Lisa, was so notorious that people all over the continent spoke of it. The detailed, candid naturalness of the figure, her elegant but tangible attitude, the smooth and delicate shape of her hands, her piercing gaze, made the lady’s effigy so realistic that it was already considered as the superlative example of any lifelike portrayal.

Portrayal of Monna Lisa del Giocondo. Leonardo da Vinci. 1503 - 1504.

Michelangelo, on the other hand, had just completed the towering but impressively anatomically accurate statue of the David, which was already on the path of becoming one of Florence’s most treasured symbols. The unthinkably accurate human depiction that Michelangelo had been able to carve out of a cold marble stone was a magnetic masterpiece of force and refined realism, as its imposing stature and colossal built took nothing away from the mesmering details of the veins throbbing in its hand or the wrinkled skin on the vast thumb.

David. Michelangelo. 1501 - 1504.

Additionally to their own level of mastery and notoriety, the suspected possible rivalry between Leonardo and Michelangelo was, to the Great Council, a welcome incentive to gain even more popularity and fame to the endeavor, as Pier Soderini exorbitantly defined this collaboration as a competition to ascertain which of the two was the greatest artist in the world (Jones, 2010, p.5).

In present times the idea of the antagonism between these two artists mainly comes from a line in Giorgio Vasari’s Le Vite, in which the author describes the relationship beween Leonardo and Michelangelo as characterized by a “great disdain” (Vasari, 1538, p. 11557).

An additional source, the Anonimo Magliabechiano, recounts an episode where Michelangelo, invited by Leonardo to partecipate in a conversation in front of Palazzo Spini and taking this invite as a mockery, responded so harshly to the other artist that Leonardo ended up blushing of embarrassment. (Jones, 20) More than an open rivalry, however, the relationship between the two seemed to be defined by their great differences, as the two men couldn’t be more diverse. Leonardo was charming and pleasant man, always willing to delve into conversation and congenial debate, notoriously well-liked by everyone around him. Michelangelo, on the other hand, fully embodied the archetype of the short-tempered, passionate and reclusive artist, who favored being alone and fully immersed in his work and was known for being prone to anger out-bursts.

This rumors of animosity between the two at the time did nothing but render the endeavour furtherly impressive in its nature: the two most notorious artists of the period united in a major artistic project, fueled by their love for the city that gave them so many opportunities. It was an idea that would undoubtedly imbue the enterprise with a memorable level of fame and prestige.

The Battle of Anghiari. Gérard Edelinck. 1660.

It was, however, for both of them, an incredibly challenging project, both because of the huge size of the walls of the Great Council Hall and because of the uniqueness and novelty of the subject matter. And, as a matter of fact, neither of them winded up completing their work. Leonardo, after trying for the first time to use the encausto technique to dry his mural painting, irreparably damaged his work; while Michelangelo, after Leonardo’s failure and probably already taken with future commissions, abandoned his painting and left for Rome. The walls and ceiling of the Great Council Hall were, decades later, painted by Giorgio Vasari (1511 - 1574), and his art survives to this day and still adorns the room.

The Battle of Anghiari Leonardo was entrusted to paint the Battle of Anghiari, which took place on the 29th of June, 1440 between the Florentine army and the Milanese troops sent by the Duke of Milan, Filippo Maria Visconti (1392 - 1447). After leaving a trail of destruction, pillaging every village in their way, the Milanese army finally came face to face with the Florentine forces, at that point aided by the troops of both Venice and the Papal State. The final fight happened in Anghiari, near Arezzo, where the Florentines were able to trap the Milanese army on a bridge, rendering it impossible for the enemy to freely unleash their fighting potential. The Battle of Anghiari was of crucial significance because it de facto ended the Milanese expansionistics aims towards central Italy.

There are no original sketches left of Leonardo’s full work, but knowledge of this composition has come to us through several derivative copies. The most famous of these replicates is the Tavola Doria, most probably dating back to the second half of the 15th century, but there are other two anonymous copies, just as notable, one of them notably reprised by Pieter Paul Rubens (1577 - 1640) during the 17th century. In addition to these, several authentic sparse drawings illustrate some of the exceptional details Leonardo planned to insert in this painting.

Tavola Doria. 1563.

Leonardo chose for his work to focus on a particularly denotative moment of the event: the violent, fierce and pivotal struggle between the two opposite commanders to gain possession of the Milanese banner and effectively end the battle. The scene is centered around a fluid yet extremely expressive central clash of bodies, involving, on the left, the heads of the Milanese army, Nicolò and Francesco Piccinino, both wearing crazed, ferocious and almost inhuman expressions, and on the right, instead displaying an enviable solemnity under their elaborate helmets, the leaders of the Florentine army, Ludovico Scarampo Mezzarota and Pietro Giampaolo Orsini. This dynamic composition, however, thematically culminates in the nucleus of the whirling vortex of human and animal bodies. Almost at the center of the painting, the two horses observe the unfolding of the dramatic happenings with a look of pure, dreadful terror in their eyes. It's as if, aware of the useless brutality of violence, they’re trying to communicate the conclusive and undoubtfully terrible essence of the scene and of war itself, which Leonardo notoriously defined a "beastly folly" (Da Vinci, 1947, Part Second - 173).

Horseman's head. Leonardo Da Vinci. 1503.

The Battle of Cascina Michelangelo was assigned the highly symbolical Battle of Cascina, fought on the 28th of July, 1364 between Pisa and Florence. This conflict was particularly meaningful and charged with huge political connotations because at the time of the commission, in 1504, Pisa and Florence had been at war for about ten years, as the former kept fighting strenuously to maintain its independence from the latter. The Battle of Cascina was a major demonstration of the alleged superiority of Florence, as the battle reached its peak when the Pisan army, after an attempted ambush on the enemy on the Arno river’s shores, was inevitably vehemently defeated by the Florentines.

Michelangelo’s original sketches of the complete design, like Leonardo’s, have been lost to time. His full idea of the composition has survived to this day through copies, the most notorious example being the drawing executed in 1542 by Bastiano da Sangallo (1481 - 1551), apprentice and associate of Michelangelo. There are, however, some authentic sketches of studies of specific figures Michelangelo then inserted in his final drawing.

Copy of Michelangelo's Battle of Cascina. Bastiano da Sangallo. 1542.

Michelangelo’s choice of subject matter was a frozen moment in time. He depicted the scene a few beats before the surprise attack, as the soldiers, worn out by the terribly heated weather, had decided to enter the river to gain some relief in the water. The composition Michelangelo ideated is a characteristically monumental study of naked male anatomy, as he had the chance to portray a wide variety of postures and behaviors. In this potent tableau of bodies any conceivable and plausible position is reported in detail: there are soldiers lying down completely, lifting themselves up on their arms, unsheathing their swords, oustretching their arms to put on their armor, running, being submerged by water. In a typically michelangelesque fashion, the muscular structure of the bodies, along with their dynamic exertions, undoubtedly contribute to the vibrancy and fervor of the depiction. The composition remains, however, despite the chaotic nature of the event, surprisingly well-structured , mainly because of its narrative aspect. The drawing is to be seen on three different horizontal planes: in the immediate forefront the soldiers are exiting the river, climbing the rocky shore; in the middle ground, some of them are dressing up, preparing to fight; and in the background, mostly turned away from the rest, those who are fully armored are already bracing themselves for the imminent battle.

Nude from the back. Michelangelo. 1504 - 1505.

The difference between Leonardo and Michelangelo’s composition is striking, but their works are extremely emblematic of their diverse personalities. Leonardo’s elegantly chaotic and emotional swirl of bodies conveys a feeling of almost desperate anxiety, whereas Michelangelo’s intense but far more structured formation of bodies fully epitomizes the tension and suspense that preceeds the fight.

Despite both of them having given up on the project and subsequently leaving the city, the cardboards with their respective sketches, kept in the Great Council Hall for years, almost immediately reached an extraordinary level of fame. Artists from everywhere came to admire the magnificent compositions, trying to learn how to express strength and passion in such an invidualistic yet universal and all-encompassing way, so much so that, as the artist Benvenuto Cellini described it, the experience was comparable to a “school of the world”.

The impact that these never-completed masterpieces left on the artistic world of the time is, not surprisingly, impressive in its essence. Leonardo and Michelangelo would respectively and almost immediately move on from what they both considered a failed attempt at a grandious experiment, but even their abandoned tries at this pursuit would become a fundamental cornerstone of the notion of the modern artist.

Whether these two artistic geniuses were actual rivals or not, their short-lived and ill-fated cooperation, despite leaving behind almost no material traces, has been so consistently impactful and inspirational that its almost mythical existence still lingers to this day.


Da Vinci, L. (1947). Trattato della Pittura. Lanciano: Carabba Editore. Retrieved from

Editorial staff. (2021). La Battaglia di Anghiari: il capolavoro di Leonardo Da Vinci che non fu mai dipinto. Finestre sull'Arte.

Editorial staff. (2021). La Battaglia di Cascina: quando Michelangelo gareggiò con Leonardo Da Vinci. Finestre sull'Arte.

Jones, J. (2010). The Lost Battles. Leonardo, Michelangelo & the Artistic Duel That Defined the Reinassance. London: Simon & Schuster UK Ltd.

Vasari, G. (1538). Le vite de' più eccellenti pittori, scultori, e architettori (Kindle version).

Visual Sources

Unknown. View of Florence known as Pianta della Catena, 1470, 1887. [Tempera on canvas]. Retrieved from

The Great Council Hall or Salone dei Cinquecento as it appears nowadays. [Photo]. Retrieved from

Leonardo Da Vinci. Portrayal of Monna Lisa del Giocondo,1503 - 1504. [Oil on poplar panel]. Retrieved from

Michelangelo. David, 1501 - 1504. [Marble sculpture]. Retrieved from

Gérard Edelinck. Fight for the banner, 1660. [Burin engraving based on Pieter Paul Rubens' sketches]. Retrieved from

Francesco Morandini known as Poppi (attributed). Tavola Doria, 1563. [Oil on canvas]. Retrieved from

Leonardo Da Vinci. Horseman's head, study for the Battle of Anghiari, 1503. [Red and black chalk on pink paper]. Retrieved from

Bastiano da Sangallo. Copy of Michelangelo's Battle of Cascina, 1542. [Oil on panel]. Retrieved from

Michelangelo. Nude from the back, 1504 - 1505. [Ink and pencil on paper]. Retrieved from

Author Photo

Elena Maiolini

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