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In bed with Niccolo Machiavelli

The man we all know as Niccolò Machiavelli was, without any doubts, an ingenious and rational diplomat. In our studies we have seen how he could be defined as a fundamental patron of the political sciences and some have gone as far as to call him the deliberate father of modernity. He is, in a way, our father as well. As members of Study Association Machiavelli, we all have him as our proverbial daddy.This serious and intimidating man took into his hands to describe the slyness of the politicians in his times, teaching future princes how to keep hold of their beloved power.In 16th century Italy, his book The Prince became quickly known as a book that taught evil, because of the man’s unique ways of justifying violence. The book was shunned and disgraced by the church to then become a standard pillar in political and philosophical education.But what was this Machiavelli like in his private life? Our work has the purpose of opening your eyes and mind to the way we look and this cold and calculating Italian man.

One of the most illuminating letters written by Machiavelli in 1509 to his friend and fellow intellectual Luigi Gucciardini, describes in rather dramatic fashion way a particularly singular encounter of his. While away from his wife for work, Machiavelli found himself slave to his urges and was lured inside the house of a courtesan, a harlot. However, the house was so dark, that it made it impossible for the man to see, which did not stop him from “giving her a good hump”. After intercourse, pervaded with curiosity he found a lamp and shone light on the woman and “my God, she was so ugly that I almost dropped dead…”. The courtesan had “a tuft of hair, half white and half black, the top of her head was bald which allowed you to see several lice taking a stroll… Her eyebrows were full of nits; one eye looked down and the other up. Her tear ducts were full of mucus… Her nose was twisted into a peculiar shape, the nostrils were full of snot and one of them was half missing. Her mouth looked like Lorenzo de Medici’s, twisted on one side and drooling since she had no teeth to keep the saliva in her mouth. Her lip was covered with a thin but rather long moustache”. Machiavelli’s reaction to seeing the woman with whom he had coital relations appearance was so strong to cause him to vomit on her. Now, this story is only the tip of the iceberg that was the wonderful and exciting life of one of the most prominent intellectuals of his century.

16th century Firenze was an apparently pious city with an immoral heart, where people were characterised by a devout exterior but where nights filled the city with what could only be described as depraved behaviour. An example of this can be seen with the “tamburazioni”, anonymous letters of complaint regarding unholy behaviour left in churches or for the police by concerned citizens. Our beloved and well-respected citizen Machiavelli was cited often in those pieces of paper, most notably in one stating how Sir Niccolo Bernardo Machiavelli was “humping the backside” of a certain Curly-haired Lucretia. This was a grave accusation of sodomy, as anal sex was illegal in any form in Firenze at the time. The accusation hid some veiled allegations of homosexuality as well, which was a theme often brought up around Machiavelli. Apparently, both Niccolo and his intellectual friends did not discriminate by gender in their sexual encounters. In a letter dated 1514, to his friend and fellow diplomat Francesco Vettori he tells the “juicy episode” happened to their common friend Giuliano Brancacci who one day went hunting for “roosters” and found a “young goldfinch” which he brought to a dark corner with him. This types of metaphorical jokes at the expense of their friends’ sexual escapades were not uncommon, even though almost never explicit. In a later letter, Vettori told Machiavelli of how he saw his son holding hands and whispering and doing stuff like that with another boy, asking him to be lenient, and reminding him of his past exploits which we are starting to understand.

Like us, Machiavelli spent a considerable time of his life at university. And while you would expect such a brilliant man to be a boring nerd, his adventures tell us quite the opposite story. His time at university was filled with gambling and parties. At these parties, wine was in abundance. Machiavelli and his friends would drink all night, and wrote the most obscene poetry you can imagine. As it befits young students at university, he and his poetry writing friends would spend long nights with ladies of dubious reputation. But what if one of your dear friends can’t come to a party? You write him a drunk message, obviously. The friends of Machiavelli did precisely that when he couldn’t attend a party. And it just happens to be, that we found that letter. They wrote to him what all dear friends write each other when a dear friend misses a party. They described the numerous ladies in attendance, especially ones of dubious reputation. One of them got a special mention in the letter to Machiavelli, as she was “waiting for you with her privates open”. As we can see, Machiavelli wasn’t the party pooper we would expect from such a cold diplomat, he was actually quite the party animal.

In this last letter we are covering for this article, Machiavelli writes again to his friend, Vettori. This letter is believed to consist of the only description of Machiavelli’s love for another man to date. He speaks in such a gentle way, that it is almost like it is written by an entirely different man than the man whose work was banned by the church. In the letter, he refers to extraordinary love, hinting at a homosexual relationship. This is also evident in the response by Vettori, in which he quoted a poem referring to a man loving another man. He writes: “I found love in such a gentle, delicate, noble creature, that by nature or accident I could not love or praise it as much without it being deserved. Do not think that Love took me in ordinary ways, because, knowing that those would not be enough, it took extraordinary ways that I did not know of and would not look at. You should just know that, near my fifties, this alone does not offend me, neither do the harsh ways surprise me, neither does the darkness of the night shock me. Everything seems slow to me, and at every desire we eat differently and against what should be mine, I accommodate. And while I seem to me to be in great messes, I feel inside such sweetness, both for the rare aspect being given to me and for being part of this memory, that I would not get rid of this for every thing of this world”. 


As we have seen, Niccolò Machiavelli, is a man with many facets. Not only was he a crafty politician and a so called “teacher of evil”, he is also a romantic and a “teacher of love”.

To conclude this article, we would like to share more quote by our proverbial daddy with you. In this particular letter, he is speaking to a friend of his who has apparently has found true love. We would also like to share Machiavelli’s wise advice with you, dear students and members of this lovely organisation. 

“I can only tell you to freely follow love, because that pleasure that you can take today you may not take tomorrow and if things really are as you have described them, I envy you more than the King of England! I beg you to follow your own inclinations and do not let it go for any reason, because I believe, believed and will always believe that what Boccaccio says: it is better to do and regret than to not do and regret!”

Author’s note:

Due to the crude nature of Machiavelli’s language, we have taken the artistic liberty to change some words into more appropriate ones. If this enrages you and you wish to read his original documents, they are easily found online.

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