A Prince, Leonardo Da Vinci and Tupac walk into a bar....
The origins of Machiavellianism, and how power can depart as quickly as it arrived
Renaissance Italy was an era that produced some of the greatest art and technological innovation of the middle ages. Da Vinci and Michaelangelo were the stars of the era and are rare examples of names that still ring bells in the greater zeitgeist five centuries later. The two men actually had a bitter rivalry, which came to a head during a showdown in which the two geniuses worked on murals at the same time and place, mere feet from each other at the Palazzo Vecchio. Like two tech bros gunning for the same promotion sitting in cubicles next to each other. But that’s a story for another time.
500 years ago, the position of “Pope” was much different than it is today. He was effectively the King of the Papal States, and not merely a religious leader. Italy was not the united country that it is today, and the “Papal States” included places like Rome and Bologna, but not the whole of Italy. This fractured version of Italy created opportunity for warlords to wreak havoc on vulnerable cities. Renaissance Italy wasn’t just painted with genius on canvas, it was painted with blood on the streets.

In the course of reading Walter Isaacson’s Da Vinci biography, I learned about one of the most ruthless warlords of the time. Cesare Borgia was the son of The Pope (yes, the Pope could have kids, in fact this pope had many children by many women), and was handed an army to help him manipulate, murder and maim anything standing between him and additional territories for the family. Nepotism much? Picture a Renaissance era Kendall Roy, except his dad most definitely was not telling him “You’re not a killer.” Would be curious to know how the Pope reconciled the mass murder and sacking of cities that was sanctioned by His Holiness himself, but I digress. Was probably all part of god’s plan. After all, I can’t recall the Catholic Church ever having a scandal or being involved in anything that wasn’t 100% righteous and holy, can you?
Borgia became the inspiration for Niccolò Machiavelli’s book, “The Prince.” The read is actually more of a pamphlet than a book, created as a “how to” manual for future Princes or those in power. Machiavelli was a diplomat as well as an author at the time. He travelled together with The Prince and Leonardo Da Vinci, and thus was granted an intimate look at the way Borgia operated.
If you’re asking why Da Vinci was there...besides being an artist, Da Vinci was also one of the great military technologists (or wannabe technologists, depending who you ask) of the time. Despite being a pacifist who wouldn’t even eat meat because he loved animals, he enjoyed creating weapons and devices that could maim and kill. The duality of man, I suppose.
The entire premise of “Machiavellianism” is that every action is a “means to and end”, ie you can justify essentially any cruelty or utter lack of morals if it helps you to reach the end goal. In a display of cruel and diabolical genius, Borgia turned his own murderous rampage into a political royal flush. After ordering General Lorqua to brutally sack a city, he decided Lorqua had served his purpose. After serving said purpose, Borgia had him arrested, executed, then cut into two pieces.
Next, his body was dumped in the town square like like an overcooked ribeye so all the towns people could see how Borgia had “saved them.” No one knew the real story. To the locals, Borgia was not the murderous tyrant. He was the savior who removed the real tyrant. The locals cheered and loved the very man who ordered all of the rape and murder in the first place. Borgia got the territory, and he got the people to think he was the savior. What are a few thousand corpses between friends?
Machiavelli watched all of this unfold and thought it nothing more than political and diplomatic genius. "Thus he made sure that the cruelty was attributed to one individual, not to himself, and after this, he could not have found a better pretext to justify himself and to begin new policies." Machiavelli was not appalled by this action, he was impressed. A means to an end, I suppose.
Borgia eventually lost power and influence when his dad (The Pope) passed away. There’s an analogy about Lebron and Bronny to be had here, but I’m of course far too mature to make that joke. After the death of his father, Borgia was arrested by the new Pope’s forces, but escaped and fled to Spain. During a military campaign in which he was defending a small castle (not even a big castle, what a shame), Borgia recklessly got separated from his troops and then was ambushed and stabbed to death. It’s unclear whether he was then cut in two and displayed in the town square.
Despite his anticlimactic ending, the influence of Machiavellianism has carried on for centuries. My first encounter with the concept was when 6th grade Matt discovered gangster rap and listened to Tupac’s “The Don Killuminati: The 7 Day Theory.” ‘Pac had read “The Prince” in prison, and the album reeked of the common themes from the book around revenge, manipulation, and power. Elsewhere in popular culture, my “Game of Thrones” fans likely remember Lord Peter Baelish who famously said “chaos is a ladder.” Machiavellian indeed.
The concept appears around us every day. Think of the world leader authorizing killing and war under the pretense that the killing now will prevent more killing later (the atom bomb was perhaps the most deadly “means to and end” in world history). Or it could be when the coworker who throws others under the bus or takes credit for things they didn’t do to achieve the “end” that is a promotion or raise. Or the self driving car company that kills a bunch of people during beta testing because in the end “less people will die with self driving cars and the world will be better for it.” And what about the algorithms that drive clicks and make us hate each other but achieve the “ends” of “shareholder value?”
None of this is to say that every version of Machiavellianism is bad. Sometimes we need to know how to “play the game” in order to get what we want. Other times, it can make us into destructive, selfish assholes. Often the “getting what we want” and “destructive selfish asshole” part are not mutually exclusive. Just remember, the tactics we use to rise to the top burn bridges along the way. The fall is much faster when said bridges are on fire. Just ask “The Prince” Borgia how things turned out on his end.
Good read. I don't know much about that era. Learned alot. And you see it today.
Would you recommend the Napoleon book or the Isaacson book on Da Vinci?