Italy was not a unified country when Machiavelli wrote The Prince, and instead it consisted of city-states that were often at war with either each other or France, Spain, Switzerland and the Holy Roman Empire as each party fought for control over the land. Machiavelli saw the restoration of the republic in Florence when he was young, as the Medici family, who had been ruling the country for some 60 years, were expelled. Machiavelli soon acquired a lot of power in the republic of Florence, as a counselor and a diplomat to the republicans. During this time, he learned the methods of the state from Cesare Borgia and his father, Pope Alexander VI, which influenced The Prince.
He was responsible for the Florentine militia for three years - it was common for armies of Italian city-states to mostly consist of mercenaries, whom Machiavelli greatly disliked (which can also be seen in The Prince as he does describe them to great detail at one point). He instead staffed the army with Florentine citizens, which proved to be quite successful - until the Medici, backed by the new Pope Julius II and the Spanish, defeated Florence.
(Pictured: Portrait of Niccolo Machiavelli, who really does look like a sly person)
This spelled the end of the Florentine city-state and republic, and the Medici rose to power again. Machiavelli was dismissed from the office, imprisoned, and tortured with accusations that he partook in a conspiracy against the Medici family (which he consistently denied until he was released), and later exiled. He kept writing and studying political theory and philosophy, and remained close with some politically active people during the Medici's rule. The Prince was dedicated to Lorenzo de Medici, the Florentine ruler at that time. Machiavelli hoped that it would allow him to regain his power in the government. The book was received poorly due to how tyrannical and politically manipulative and, in general, unpleasant it was, and practically ignored by the Medici - who were, soon enough, deposed and driven out of Florence again. Machiavelli never gave up on his political ambitions, but at this point his reputation - as the author of The Prince and for being connected to the Medici - preceded him. He was rejected by the restored republic. His health deteriorated soon thereafter, and he died without realizing his ambitions.
http://www.historytoday.com/vincent-barnett/niccolo-machiavelli-%E2%80%93-cunning-critic-political-reason
https://en.wikipedia.org/wiki/Timeline_of_Niccol%C3%B2_Machiavelli
I think Fortuna or trying to run both lanes played a huge role in Machiavelli's life and ambitions. Maybe if he had stuck to what he believed in, after the Medici family lost power once again, he could have realized his life long ambitions. Or maybe he had a little more luck (Fortune) he could have again become part of the government to rule. "Sometimes its better to be lucky than good".
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