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As a side question, I was told in high school that The Prince was satire, and that that was largely lost on later generations. I never really found any sources on that though, so I'm curious if that's at all true or if she was just kind of pulling it out of her ass?
Henry VIII of England may have been greatly influenced by "The Prince". While there is no irrefutable evidence I'm aware of that proves Henry read it, Thomas Cromwell was supposedly a devoted fan of the book. Cromwell was the most influential person in Henry's life for many years, so I doubt he would have neglected to mention the book at some point. As Henry VIII was a voracious reader anyway, especially of political theory, it is probable that he read and was influenced by "The Prince". Historians seem to be divided on the subject, though.
Here is a quote from "The Cambridge History of English and American Literature":
No work had a profounder influence upon the thought and policy of Tudor England than Machiavelli’s Prince. It was a text-book to Thomas Cromwell; its precepts were obediently followed by Cecil and Leicester. The mingled fear and respect in which its author was held converted him into a monstrous legend. No writer is more frequently cited, generally with disapproval, than Machiavelli, and it is always the Prince...
If you're interested in reading further, there is an entire book devoted to the subject of whether Thomas Cromwell was influenced by "The Prince". Thomas Cromwell: Machiavellian Statecraft and the English Reformation
Prince Bandar bin Sultan bin Abdulaziz, who was the long-serving Saudi ambassador to Washington known as 'Bandar Bush', actively uses Machiavelli's work as a guide. Simpson's biography of Bandar is titled The Prince partly in reference to that connection.
As an example of Bandar's use, we can examine the build up to the Gulf War (now beyond the twenty year limit). After Hussein's invasion of Kuwait, then-U.S. President G.H.W. Bush wanted to send a letter to the Iraqi leader, urging a peaceful settlement. As related in the above mentioned biography, Bush asked his friend, Bandar, to translate the letter into Arabic. NOW, Bandar's motivation was to see Hussein ousted from power. Some of the richest Saudi oil fields lay just across the border with Kuwait, and a conquering dictator a stone's throw away was unacceptable. Saudi interests would best be served by forcing Hussein's hand, and tipping off a war with America.
In translating Bush's letter, Bandar remained faithful to the word, if not the spirit of the original. Choosing subtly antagonistic wording, Bandar manipulated Hussein's need to save face and ensured the Iraqi wouldn't back down. He didn't, and war broke out. Bandar would later express disappointment that Hussein had been allowed to remain in power.
Source (NB: the book's author is a friend of Bandar's; interest in this intimate access should be tempered by a chunky salt lick):
http://www.amazon.com/gp/aw/d/B0046LUDT2?pc_redir=1400752922&robot_redir=1
Machiavelli's conception of willpower and overcoming the vagaries of fate and chance through Renaissance virtue (namely, wit and willingness to be a total shit to get what you want) was describing a broad cultural trend being embraced by Europe as a whole, specifically alongside the development of the bourgeoisie. The idea of the Protestant work ethic and ideas about wealth and success emerging during the Protestant Reformation were all concepts described by Machiavelli in Italy. It was a broad trend that developed alongside European urbanization and the growth of the merchant class and a free peasantry (and, not coincidentally, the opening of foreign trade, plantations, and early modern capitalism).
You see this (not just The Prince, but Machiavelli's work in general) come up everywhere in early modern history. Check out Max Weber's Protestant Work Ethic and the Spirit of Capitalism, Edmund Morgan's American Slavery, American Freedom, and Perry Anderson's Lineages of the Absolutist State for a broader view and how Machiavelli fit into it. Check out Boal's Theatre of the Oppressed for how Machiavelli fits into the dialectic of artistic development (it's a lot).
I'll always tout Morris's Venetian Empire and Blackburn's Making of New World Slavery for the development of the plantation system and slavery by the Italian republics in the Mediterranean, which predates Machiavelli.
I remember reading a Cracked article saying The Prince was supposed to be satire but was received as actual views on governance. Any truth to this?