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Niccolò Machiavelli (1469 - 1527) was a Florentine writer, philosopher, and political theorist active at a time of great chaos and turmoil throughout Italy. He is best-known for writing The Prince, a handbook for the ruling Medici family on how to most effectively run a principality. Due to The Prince being his best-known work, coupled with the fact that few who quote it have actually read it, Machiavelli's name has become a byword for being a ruthless, manipulative, backstabbing bastard; so much so that in Christopher Marlowe's Doctor Faustus, Machiavelli is presented as one who has made a Deal with the Devil, and the term Old Nick to refer to The Devil may also be derived from his forename.

This reputation is perhaps undeserved as some of his other works, notably Discourses on Livy, are all about successfully running republics, and even in The Prince he states that a republic is the best form of government. In the eighteenth century the view that the book was actually an elaborate parody became fashionable given both the nature of Machiavelli's other works and the fact that The Prince was written just after he was stripped of his power, imprisoned, and tortured by the Medicis. In early nineteenth century Germany it became fashionable to suggest that The Prince needed to be judged relatively. Hegel argued that it was written for a certain time and certain locale and to judge it based on contemporary morality and from the perspective of someone living in a unified nation state was unfair. Since the mid-twentieth century, the most common interpretation of The Prince is that it simply describes "what men do, and not what they ought to do" and that it is the first true work to deal with politics as a branch of science and not ethics.

However, one must be careful not to assume that Machiavelli was truly pro-democracy. In Discourses on Livy, he takes the time to state that pure democracy isn't a great idea either, and the best form of government is one that combines democracy, aristocracy, and monarchy so that the different social classes can keep each other in check. On the other hand, the liberal movement which (openly or otherwise) adopted Machiavelli's philosophy more or less took the same opinion. Indeed, modern representative democracy would rather please Machiavelli, as it more or less reflects his ideals (a popularly-elected legislature is not a democracy as he understood it, but close enough to serve in the position in his three-in-one system;[1] the modern investment of a great deal of power in directly-elected presidents and indirectly-elected prime ministers is a pretty good approximation of his idea of "monarchy"; and both the role of less-representative upper legislative houses--like the US Senate and British Lords--and small, well-educated judicial courts are close to his concept of "aristocracy").

Like many of that era, Machiavelli believed that Ancient Rome was the peak of human civilisation, particularly the Roman Republic, and he often uses its example to illustrate political points.

As well as his political works, Machiavelli wrote several books of history and a number of poems and satirical novels and plays.

His works include, but are not limited to:


  • Description of the Manner in which Duke Valentino put Vitellozzo Vitelli, Oliverotto da Fermo, Lord Pagola and the Duke of Gravina to Death (1502)
  • On the method of dealing with the Rebellious Peoples of Valdichiana (1502)
  • The Prince (1513)
  • Discourses on Livy (1517)
  • Discourse of Reforming the Government of Florence (1520)


  • The Art of War (1519; no, not that one)
  • Life of Castruccio Castracani (1520)
  • Florentine Histories (published 1532)


  • The Golden Ass (1517): Not an original work, but a translation of a novel by the Roman Apuleius.
  • The Mandrake (1524): An original comedy, his greatest popular success.
  • Belfagor arcidiavolo (published 1549)

Tropes related to the actual man

  • Admiring the Abomination: Machiavelli's admiration for Cesare Borgia may count as this.
  • Born in the Wrong Century: He shared the Renaissance mentality of being several centuries ahead of his time and of wanting to live in Ancient Rome. See the Cosplay example below.
  • Cosplay: A truly weird example, but Machiavelli actually used to dress up in a toga and pretend to be a Roman. Overlaps with One of Us.
  • Deadpan Snarker: A common way of portraying Machiavelli in fiction but also Truth in Television. This can be seen in his account of a dream he had where he saw all the saints in Heaven and philosophers like Plato in Hell. When he told this dream to his friends, Machiavelli said that he'd rather be in Hell with interesting people than in Heaven where everyone was boring and good.
    • There is also another story that when he found out his father had been buried in the same grave as some other people, he replied, "Well at least he will have company".
  • The Good Chancellor/Evil Chancellor: Machiavelli was Chancellor of the Florentine Republic. YMMV on which one you believe he was.
  • Historical Villain Upgrade: Perhaps undeservedly.
  • The Man Behind the Man: Machiavelli is often portrayed this way with respect to both Cesare Borgia and the Florentine Republic. In actual fact, he never had much influence over the affairs of his idol or his city, something he often lamented, since he thought he could do it better.
  • My Country, Right or Wrong: Machiavelli was a patriot who wanted a united Italy at a time when no one else particularly thought it was possible. This may explain why he wrote a book about how a dastardly, wickedly cunning, violent man would be a good ruler.
  • No Celebrities Were Harmed: After his death his son found an unfinished play that Machiavelli had been working on that contained several thinly-veiled and quite cynical parodies of several important men in Florence.
    • Also in The Mandrake, there is a particularly idiotic character who is clearly based on Piero Soderini.
  • Renaissance Man: Amongst other things, Niccolo Machiavelli was a poet, a playwright, a musician, a statesman, a diplomat, a writer, a philosopher, an humanist, an historian and a patron of the arts.
  • Self Deprecating Humour: Somewhat bizarrely. According to his friends, Francesco Vettori and Francesco Guicciardini, Machiavelli frequently put himself at the butt of other people's jokes. A sort of self-imposed Butt Monkey.
  • Tall, Dark and Snarky
  • Worthy Opponent: He considered Caterina Sforza, the Countess of Forli, to be one of these. The Countess managed to hold out much longer than any of Cesare Borgia's other (male) opponents and Machiavelli, who acted as the go-between, witnessed her forceful personality first-hand.


  1. To elaborate, Machiavelli considered Rome the model, and Rome was a single small republic that conquered and collected tribute from other city-states and thus could have a direct-democratic element in the city. The idea of representative government was essentially an English invention, and the idea that the territory of a republic could--indeed, should--encompass thousands of square miles was straight from the mind of James Madison--who, incidentally, made no bones about his interest in Machiavelli.
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