Da Vinci and the Machines

Progress is paradoxical. It also requires a belief that it's possible.

Did da Vinci paint this portrait of Machiavelli?

Da Vinci Meets Machiavelli

In 1502, Leonardo da Vinci and Niccolò Machiavelli found themselves under the banner of Cesare Borgia, the infamous and ambitious son of Pope Alexander VI. Leonardo, the master artist and engineer, had been brought on as Borgia’s military architect, tasked with designing fortifications and devising machines that could secure Borgia’s grip on his volatile territories. Machiavelli, meanwhile, was there as an envoy from Florence, sent to observe the strategies Borgia employed to consolidate power across the fractured landscape of Italy.

Italy was a battleground of ruthless ambition by the turn of the century. Political power was seized and lost in shifting alliances, and city-states hung precariously between chaos and stability. The Medici in Florence, the Sforza in Milan, and the Orsini in Rome all vied for supremacy, their alliances shifting with the fortunes of war. Borgia, embodying the chaos of the era, had already secured his power by treachery, famously ordering the murder of his own brother Giovanni in 1497 to eliminate a rival. Now, Borgia sought to carve out an empire in the Romagna region, a territory known for its strategic importance and contested by various warring factions.

Da Vinci, Walter Isaacson's 2005 biography, gives a vivid account of Leonardo and Machiavelli traveling with Borgia. Imagine the scene: Borgia caravanning across Italy to survey his territory, with one of the most famous painters from Florence in tow. Not to be outdone, Machiavelli, the future author of The Prince, accompanied them—a work that was no doubt taking shape during his travels in 1502. Da Vinci was there to apply his engineering genius to both nature and human artifact: designing dams, and architecting stronger walls and fortifications to secure Borgia’s expanding empire. Machiavelli was there as a lawyer and political observer. Between them—Da Vinci and Machiavelli—we witness the new face of Italy emerging: the invention of both the political and the physical, the confluence of art, engineering, and statecraft that would shape Italy, and indeed the Western world.

The Mechanical Man

Leonardo da Vinci was a polymathic genius, living in worlds both seen and unseen, as much a part of the imagination as the reality of 16th-century Florence. Like many great minds, his life was filled with paradox. By day, he painted masterpieces; by night, he dissected cadavers in secret—not out of mere curiosity, but to master the mechanics of the human body, knowledge that he meticulously applied to his art. His notebooks brim with sketches—muscles and tendons, intricate water wheels, fantastical flying machines. Flip through these voluminous drawings, and it’s impossible not to marvel at the breadth of his vision. What truly stands out is the detail and specificity of his sketches. He seemed obsessed with capturing the minutiae of the world. He was the mechanical man.

He wasn’t a reductionist. His genius lay not in deconstructing the world, but in reassembling it into something greater than the sum of its parts. His paintings are so famous and familiar that we often overlook their profound magic. As Walter Isaacson notes, the Mona Lisa—a small and seemingly unassuming portrait, as any visitor to the Louvre knows—appears ineffably alive. Her eyes seem to follow you, her enigmatic smile hints at something mischievous, as if she concealed a secret. There’s a mystery in her expression that defies complete analysis. That was Leonardo’s gift: to transform the mechanical into the divine, to create art that transcends mere depiction and captures the essence of life itself.

Leonardo’s notebooks reveal an insatiable curiosity and a relentless drive to understand the broad complex sweep of the world. He sketched everything from the swirling patterns of water to the mechanics of war machines. Isaacson describes how Leonardo’s drawings of the human heart, made after dissecting a cadaver, are so precise that modern medical professionals still reference them. Yet, for Leonardo, these were not just exercises in anatomy. There’s a palpable sense that they were part of a grander vision, a pursuit to integrate knowledge across disciplines. He seemed, ultimately, to be searching for the connection between the physical and the metaphysical.