August 7, 2019 | Kyle Climans

42 Sinister Facts About Niccolo Machiavelli

“Of mankind we may say in general they are fickle, hypocritical, and greedy of gain.” –Niccolo Machiavelli

He bears one of the most sinister-sounding names in human history, but this is because of one book he wrote: The Prince. This book has been hailed—or reviled—as a treatise on the pursuit of power, regardless of any morals. The phrase “the end justifies the means” has most often been associated with this man whose very name has become a term for people who make that creed their mantra. So what kind of a vile man could have dedicated his life to teaching people how to succeed in taking advantage of each other for their own gains? As with so many tales, the story of Niccolo Machiavelli is much more complicated than history would have you believe, which is why we have provided you with the list below.

1. Just to Clarify

To properly define Machiavellianism, the word is a term to describe a single-minded pursuit of selfish gains. Most often this translates into a selfish pursuit of personal power. As quoted from the English Oxford Living Dictionaries, Machiavellian actions are described as “Cunning, scheming, and unscrupulous, especially in politics.”

Niccolo Machiavelli FactsGetty Images

2. A Psychiatrist’s Nightmare

In the world of psychology, Machiavellianism has been categorized as one of three personality traits known to experts as “the dark triad.” These three personality traits (Machiavellianism, narcissism, and psychopathy) are a sort of unholy trinity which inspires malevolent and destructive behavior in humans. To make matters worse, they also tend to overlap, and feed into each other.

Niccolo Machiavelli FactsPixabay

3. Where it All Started

Machiavelli was born on May 3, 1469 in the Italian city of Florence. He was third child of Bartolomea di Stefano Nelli and Bernardo di Niccolo Machiavelli. Machiavelli’s full name was Niccolò di Bernardo dei Machiavelli, so we can see some naming traditions living strong in his family!

Niccolo Machiavelli FactsWikimedia Commons

4. Those Were Rough Days

Machiavelli grew up and lived during a particularly brutal time in the history of Europe. Italy was divided into city-states that waged brutal wars with one another, even as France, Spain, and the Holy Roman Empire also weighed in on land grabs and short-lived alliances. In case you’re still not sure, this was a time period when the popes would personally become involved in these wars as well and even lead war efforts.

To be honest, anyone would be cynical growing up in those times!

Niccolo Machiavelli FactsPixabay

5. Hail the Republic

By the time that Machiavelli was 25 years old, in 1494, the powerful Medici family had ruled Florence for sixty years. However, this changed when the family was driven out of the city-state so that the republic could be restored. Sadly, this did not consist of barricades being built with rebels asking if we could hear the people sing.

Niccolo Machiavelli FactsWikipedia

6. If Only He was an Unlockable Character

Gamers will doubtless be familiar with Machiavelli thanks to the Assassin’s Creed series. Machiavelli appears in both Assassin’s Creed II and Assassin’s Creed: Brotherhood. Admittedly, Machiavelli probably wasn’t a secret member of a league of assassins, but it’s still pretty cool how deeply the Assassin’s Creed creators delved into history to portray those games!

Niccolo Machiavelli FactsPexels

7. What an Incomplete Education!

Despite the fact that Florence was “one of the centers of Greek scholarship in Europe,” it’s been recorded that Machiavelli did not learn Greek as part of his education (which did reportedly include Latin, grammar, and rhetoric). To be fair, it wasn’t his lack of Greek language that he became known for anyway.

Niccolo Machiavelli FactsPixabay

8. Call it a Paid Internship

Once the Florentines had re-established their republic in 1494, Machiavelli was given a rather prestigious job. He was placed in the office of the second chancery, where he was responsible for producing government documents. No doubt all that practice with writing contributed to his spinoff career as a writer!

Niccolo Machiavelli FactsGetty Images

9. Book Role

In 2008, writer Salman Rushdie released his book The Enchantress of Florence, a historical fiction which Rushdie claimed was his “most researched book.” Machiavelli is a main character in the book, though he’s credited as “Il Machia,” presumably because his ghost threatened to sue Rushdie.

Niccolo Machiavelli FactsFlickr

10. So, Niccolo, Tell Me About Your Childhood! Seriously, Tell Me!

For such a well-known figure with such a sinister name, very little is known about Machiavelli’s childhood or education. His father was an attorney, so we can guess that Machiavelli came from a reasonably middle-class background, and based on his writing, Machiavelli was very widely read when it came to Italian and Latin literature and non-fiction. However, most of his early life has been lost to history.

Niccolo Machiavelli FactsPixabay

11. Hare-Brained Scheme

Incredibly, while he was with the Florentine Republic, Machiavelli once hatched a conspiracy of mad genius with famous inventor Leonardo da Vinci. Florence was famously opposed to Pisa, another Italian city-state. Machiavelli shared in the feud by forging a plot against Pisa. Frustratingly for the feud, Pisa and Florence both made use of the same river, the Arno. Machiavelli and da Vinci planned to redirect the river’s route so that Florence would get to hog all that water!

Niccolo Machiavelli FactsPixnio

12. What Might Have Been

Despite these two mad geniuses putting their heads together on this, the attempt to steal a literal river didn’t work. The technology of the time, coupled with terrible weather patterns, resulted in the plan failing. Interestingly, despite the failure, the plot left a lasting impact on Leonardo da Vinci. If you look at the Mona Lisa, his most famous accomplishment, you might notice that there is a river in the background of the painting. This river is the Arno, the exact same river that da Vinci and Machiavelli tried to steal!

Niccolo Machiavelli FactsWikipedia

13. Cesare, Meet Niccolo

The same year that Machiavelli first got married, he was assigned to be an envoy to Cesare Borgia. In case you’re confused, Cesare Borgia was notorious for being the ruthless, violent son of the man who became Pope Alexander VI (and there’s always been a long-running rumor that he and his sister Lucrezia were in an incestuous relationship, which presumably inspired George R.R. Martin).

As you can imagine, Machiavelli was deeply unhappy about being assigned to Borgia’s camp, and he got to witness first-hand the brutal policies used by Borgia as he attempted to conquer parts of Italy. However, Machiavelli would end up being inspired by witnessing such a notorious figure as Borgia when it later came time to write The Prince. He even admitted that some of Borgia’s behaviors as a leader were very effective, though he was quick to point out that a lot of Borgia’s success was due to nepotism (his dad was the Pope, we remind you) and dumb luck.

Borgias FactsWikipedia

14. Stage Adaptation

A character based on Machiavelli appears in Christopher Marlowe’s 1590 play The Jew of Malta. The character, Machiavel, narrates the prologue and introduces the play as a “tragedy of a Jew.” Machiavel also takes the time to declare that he “count[s] religion but a childish toy, / And hold there is no sin but ignorance.” We can never know what Machiavelli himself thought of this portrayal, on account of his having been dead for more than 60 years when Marlowe’s play was first released.

Niccolo Machiavelli FactsWikimedia Commons

15. This Sounds Familiar

By the fall of 1503, Machiavelli was back in Florence, and he’d been inspired to re-examine the city-state’s military situation. He was disdainful of mercenary companies, as they had gained a reputation for frequently turning traitor whenever the opportunity arose, and they were also expensive to maintain. Instead, Machiavelli looked to establish a militia made up of citizens who had far more stake in the protection of their city.

Niccolo Machiavelli FactsShutterstock

16. USA! USA!

As you can imagine from this talk of citizens forming a militia, coupled with his pro-republican stance, it has been suggested many times that the Founding Fathers of the United States of America were inspired by Machiavelli when they wrote the Constitution. In fact, Founding Father and US president John Adams wrote about Machiavelli several times in his own written works, seeing him as an inspiration.

Niccolo Machiavelli FactsFlickr

17. Europe-Trotter

Cesare Borgia wasn’t the only person who had Machiavelli as an envoy from Florence. In 1503 alone, Machiavelli traveled to the papacy in Rome and also attended the court of Pandolfo Petrucci, the man who was ruling the Tuscan city of Siena at the time.

Niccolo Machiavelli Facts

18. Monocles Flying Everywhere!

Even when the novel was first published, The Prince was seen as a shocking work by most of society. They condemned the book for its amoral tone, but this has also led people to call it “one of the first works of modern philosophy” due to the way it does away with archaic ways of thinking which were still held up as sacred during that era.

Niccolo Machiavelli FactsGetty Images

19. You Don’t Mind, Right?

One of Machiavelli’s lesser-known works was a biographical novella about Castruccio Castracani. Castracani was a duke who lived during the Middle Ages and fought a long and bitter war against Florence, among other things. However, it’s been determined that a lot of the book’s contents are fictional and serve more to promote Machiavelli’s personal philosophies rather than be an accurate re-telling of Castracani’s life.

Niccolo Machiavelli FactsPicryl

20. Inspiring Criminals

Machiavelli is referenced in Robert De Niro's 1993 gangster film A Bronx Tale. The main mob boss tells a story in one scene where he spent his time in prison reading Machiavelli’s work, which inspired him immensely. As a result, he became the man he is in the film’s present-day. No doubt Machiavelli would have been proud to know that!

Niccolo Machiavelli FactsA Bronx Tale, Price Entertainment

21. Wait, in Real Life Too?!

Bizarrely, this story of a guy reading Machiavelli in prison actually happened! Rapper Tupac Shakur was introduced to Machiavelli’s literature when he was serving a prison sentence. Shakur was so inspired by Machiavelli that in 1996, he changed his rap name from 2Pac to Makaveli. Many people forget that Tupac actually released his final album, The Don Killuminati: The 7 Day Theory, as Makaveli, and may well have gone on to use that name for years had he not been killed so soon after.

Niccolo Machiavelli FactsFlickr

22. Man of the People (and God)

In 1500, Machiavelli was sent to France as part of his work with the Florentine Republic. While spending six months in the court of King Louis XII (they had a tough time with name originality), he became acquainted with Georges D’Amboise. If that name doesn’t sound familiar, D’Amboise was a high-ranking French cardinal descended from a very noble family. He would serve as a prime minister of France, during which time he gained a high reputation for his effective administration and charity work.

Niccolo Machiavelli FactsWikipedia

23. Military Mind

Believe it or not, Machiavelli also wrote The Art of War! Before you gasp in astonishment, or angrily correct us, it was not the book by Sun Tzu that we’re talking about. Machiavelli’s The Art of War was a treatise which, among other things, disparaged the use of mercenaries and promoted the idea of “limited warfare,” where war is just an extension of politics.

Machiavelli also maintained the importance of a militia and military to protect everything about society, but given the time period he lived in, we can’t blame him for being so gung-ho for people to be armed and ready defend themselves!

Niccolo Machiavelli FactsShutterstock

24. Only This, and Nothing More

Amazingly, Machiavelli’s The Art of War was the “only historical or political work printed during his lifetime.” Even The Prince wasn’t technically published until 1532, around five years after Machiavelli had died!

Clara Bow factsPixabay

25. Brownnoser?

Fans of The Prince will know that Machiavelli dedicated this book to the very family who had him tortured and exiled. This might seem like an odd thing to do, and various explanations have been given. Some said that Machiavelli was sucking up for the slightest chance of redemption, while others say that the entire book is a sarcastic work of satire, especially given the satirical nature and sense of humor in much of his other written works.

Thomas Seymour factsShutterstock

26. God Isn’t Dead, He’s Just Fake

Machiavelli viewed religion as being man-made, yet still crucial for social order. He would suggest that a leader would benefit from religion by making his subjects devout, even if the leader himself is not. On the flip side, Machiavelli also criticized Christianity because “it makes men weak and inactive, delivering politics into the hands of cruel and wicked men without a fight.”

Niccolo Machiavelli FactsPixabay

27. Mid-Life Crisis?

In one letter to his friend, Machiavelli described his days of exile with great sadness and misery. His only solace was when he went into his personal study, which he idolizes as “the ancient courts of rulers who have long since died.” He would even put on the clothes he used to wear as an ambassador while he was in his study, as if to keep up the illusion that he was in a place of purpose and high learning as opposed to his exile.

Niccolo Machiavelli FactsGetty Images

28. He’s the Devil!

Machiavelli’s criticisms of Christianity weren’t taken well in most of Europe. One discourse published in Geneva in 1576 dismisses Machiavelli as an “atheist,” which back then was a serious insult to throw someone’s way. In fact, in France, prominent Catholics and Protestants all accused Machiavelli of inspiring the other group. Catholics saw him as a Protestant, while Protestants thought he was Catholic. A real "stuck in the middle with you" situation.

Herod The Great factsPixabay

29. A Bawdy Sense of Humor

Aside from any political, historical, or military writing, Machiavelli wrote three plays during his life, all of them comedies which expose rank corruption within his society. The Mandrake, Andria, and Clizia all revolve around wacky comedy concerning sex, affairs, marriage, and even quasi-incest. Many scholars have claimed that The Mandrake is a satire of the Medici family, but set during the time of the Florentine Republic to avoid violent repercussions. Others have stated that Andria is semi-autobiographical to Machiavelli’s life, though we’re not sure how or if that’s actually true.

Niccolo Machiavelli FactsShutterstock

30. Boy, Marriage is Hell, Am I Right?!

One story about Machiavelli revolves around his little-known comedy piece Belfagor. This work depicts satire of marriage where the devil prefers being in hell to being married. While a myth states that Machiavelli wrote it to describe his own hellish marriage, it’s just that; a myth. No evidence exists to support the idea that Machiavelli was doing anything than making a typical dad joke about being married.

Niccolo Machiavelli FactsShutterstock

31. I Was There

In the 21st century, Machiavelli made several appearances in television series depicting the Renaissance. These series include Borgia, The Tudors, and The Borgias.

Niccolo Machiavelli FactsThe Borgias, Myriad Pictures

32. History Repeats Itself so Watch Out!

Arguably the second most famous of Machiavelli’s written works, Discourses on Livy, is a retelling of the ancient Roman writer Livy’s histories of Rome. Machiavelli also adds his own philosophies to the work, pointing out how the present must learn from the past, and giving several examples to prove his point. This led French philosopher Jean-Jacques Rousseau to assert that Discourses on Livy is much closer to Machiavelli’s actual stance on politics and life than The Prince was.

The Smartest Person In The Room FactsShutterstock

33. The Mentor We Don’t Admit To Having

While it was deeply unfashionable for a long time to name Machiavelli as an influence of your philosophy (and still is, really), it’s possible to argue that Machiavelli was an influence on a large number of subsequent writers and philosophers. These include John Milton, Francis Bacon, Adam Smith, Thomas Hobbes, John Locke, and Descartes.

Niccolo Machiavelli FactsWikimedia Commons

34. Time of Death

According to his son, Machiavelli took medicine for an illness on the 20th of June 1527. However, the medicine turned violently against his body, and he became bedridden. Machiavelli died on the 22nd of June 1527 at the age of 58.

Niccolo Machiavelli FactsFlickr

35. Not Exactly as Dignified as The Prince, I Grant You

Despite being largely forgotten, Machiavelli once wrote a satirical poem titled (most amusingly) The Golden Ass. In this ultimately unfinished poem, Machiavelli writes about meeting a gorgeous herdswoman who’s in charge of an incredibly diverse bunch of animals, modeled after the Greek myth of Circe, a witch who turned men into animals. The protagonist of the poem is thus introduced to the different kinds of animals in the herd, learning about which kinds of people are turned into which kinds of animals. It ends with him speaking to a pig that doesn’t actually want to be turned back into a human, as humans are the worst. To be honest, Machiavelli may have had a point, given all that he witnessed in his life.

Niccolo Machiavelli FactsWikimedia Commons

36. The Best Guy Who Ever Lived!!

Perhaps because of the fact that The Prince hadn’t been published yet at the time of his death (though individual versions of it were indeed distributed during his lifetime), Machiavelli was a celebrated man upon his death. Buried in the Church of Santa Croce in Florence, Machiavelli was given a monument with the inscription “TANTO NOMINI NULLUM PAR ELOGIUM.” This has one of two meanings when translated into English, but the basic message is that Machiavelli’s very name is so worthy of praise that words can’t describe it.

Niccolo Machiavelli FactsWikimedia Commons

37. I Was Trolling!

Machiavelli is a deeply misunderstood person. He spent much of his career working directly within the Republic of Florence and several works that he wrote besides The Prince hold a pro-republican attitude, which flies in the face of most of what he says in The Prince.

In fact, some scholarly analysis of the famous book has indicated that people have been reading it wrong this entire time, and signs point to it being a complete satire, ie. Machiavelli actually meant the exact opposite of what he was saying. Of course, some have pointed out that Machiavelli could just have been going through phases in his life, as we all do, but historians are left to guess about that sort of thing.

Niccolo Machiavelli FactsRawpixel

38. Love and Marriage?

In 1502, Machiavelli married a woman named Marietta Corsini. The two of them would have several children together, though Machiavelli allegedly had several extramarital affairs during his life. Despite this, his marriage was apparently a pleasant one. Corsini would outlive her husband by around twenty-six years, helpless to stop Machiavelli’s name from becoming associated with everything that he himself was personally against. Though to be fair, wouldn’t that just be fitting revenge for him cheating on her?

Niccolo Machiavelli FactsPixabay

39. I’m Not Surprised! They Couldn’t Even Get a Tower to Stand Straight!

Machiavelli managed to put his money where his mouth was in terms of military matters. He was put in charge of the Florentine militia, organizing them in what he believed to be the most effective manner. His work paid off when, in 1509, Machiavelli led the Florentine forces to defeat the forces of the city-state Pisa.

Niccolo Machiavelli FactsPicpedia

40. This is How Liberty Dies

Sadly for the city of Florence, the new pope, Julius II, put his backing behind the Medici family. In 1512, Florence was besieged and retaken by the Medicis with the help of Spanish troops. The Republic fell, and Machiavelli went into exile not long after.

Niccolo Machiavelli FactsGetty Images

41. That’s Gonna Hurt in the Morning!

Machiavelli’s fate after the fall of Florence to the Medici family was not pleasant. Removed from office, Machiavelli was accused of conspiring against them in 1513. At one point he had his arms tied behind his back and was then suspended by them. This caused his shoulders to dislocate and his arms to break. Despite the brutal pain he endured, Machiavelli maintained his innocence and was released after three weeks.

Organized Crime FactsPixabay

42. An Author Under Duress

Although Machiavelli was found innocent of conspiracy against the Medici family, his time in politics was over. He was banished to his estate near San Cansciano in Val di Pesa. It was there that he began the writing career for which he has become so well known. Despite this, he only embarked on this work out of boredom and frustration at being shut out of his life’s work!

Organized Crime FactsShutterstock

Sources1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24

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