I can see why "The Prince" continues to be held up as an important piece of political literature, but also holds the rather controversial reputation of being a guidebook for psychopathic leaders. I think it's more nuanced than that. 

With books like these we have to realise the Machiavelli was writing for a very specific type of person, during a very specific time period, under very specific circumstances. I'm not a fan of people who take a political book on how to run a principality under monarchal feudalism and then try to apply it to being a manager at Costo. I think what's important to understand is at the time of writing Machiavelli was under the impression that desperate times call for desperate measures, he wanted Italy to have some sense of unification and peace and to attain this he had to look at great leaders of the past and see what they were all doing. Like anyone who looks at history for long enough, Machiavelli quickly realised that kindness doesn't get you far in the realm of Kings and wars, and that most great leaders of old were typically ruthless; although i don't think ruthless is even the best word for it, what Machiavelli truly places importance on is decisiveness. "The prince" Isn't all just "Kill everyone who gets in your way, be a meanie" like some people seem to think it is, instead Machiavelli is trying to figure out a sort of mathematical formula for keeping power and ruling well. One of the big aspects of this that Machiavelli goes over is that your citizens need to love you, you can be a tyrant to your enemies but never to your people, and the easiest way to get your citizens to love you is to simply present yourself well and treat them better than other leaders do. That tidbit alone adds some moral nuance to "The Prince" that a lot of people never seem talk about.

However, what I enjoyed most about this book was the historical elements of it. Niccolo seems to be just as much of a history nerd as he is a political fox. The sections on how leaders have ruled in the past, the failures and achievements they make, and what eventually happens to them i found all very interesting and entertainingly well written. My copy of "The Prince" has a little extra story at the back which Machiavelli wrote to his friends about this Italian duke called Castruccio, and my word is it an eye-opening account. Eye-opening in the way that it makes you realise why Machiavelli wrote "The Prince" in such a controversial manner; in which he mostly disregards morals. He wrote like that because everyone was behaving like that. Genuinely, the amount of crazy political shenanigans going down at the time in Italy is ridiculous.

Overall "The Prince" is a very enlightening window into a time and place that is far behind us, while it also discusses human tendencies and power dynamics that still occasionally plague us.