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As a teenager I read Machiavelli's The Prince with trepidation knowing it was on The List (and me being brought up Catholic).

Afterwards I couldn't really see what the fuss was about.

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Especially since there are similar works of the Catholic church, such as https://en.wikipedia.org/wiki/The_Art_of_Worldly_Wisdom

Perhaps the notion of ‘engineering’ ones legitimacy as a ruler was seen as a challenge to the established notion of legitimacy by divine right. (Esp. the role of the church in conferring that right).

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