Some of his advice rings very true today, like "get unpopular things over with quickly, but ration out popular changes over time". Machiavelli says that most people will soon forget the short burst of really bad news, and will be appeased by the constant trickle of sorta good news.
You see this with any half-competent elected government these days - do the tough things right after you're elected, and slowly pass out the goodies afterwards, ramping up the goodies as the next election approaches.
You also see morons not following this advice, as in a big company that has several waves of layoffs, you wonder if they're trying to make that sticky bandaid hurt as long as possible.
I assume the really wicked part of the book is section XVIII, how princes should honor their word.
Nevertheless our experience has been that those princes who have done great things have held good faith of little account, and have known how to circumvent the intellect of men by craft, and in the end have overcome those who have relied on their word.
Therefore a wise lord cannot, nor ought he to, keep faith when such observance may be turned against him, and when the reasons that caused him to pledge it exist no longer. If men were entirely good this precept would not hold, but because they are bad, and will not keep faith with you, you too are not bound to observe it with them.
The above seems harsh but rings true, but I'm an atheist and a cynic living in a cynical, post-monarchy world. I'm guessing had a different flavor for guys who thought the monarch derived their power straight from The Invisible Sky Giant?
PS - I am pleased to see that Wikipedia's article about The Prince names under "similar works" the "Evil Overlord List".
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