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If you really want to understand Machiavelli then Ada Palmer's post's are excellent[1]. She studies "heterodoxy, heresy, freethought, censorship and information control, the recovery of classical thought after the Middle Ages, its impact on science, religion and atheism, and the history of the book and printing."

She puts Machiavelli into context, and points out that "the ends justify the means" was really an ethical argument putting for the first time the idea that the consequences of actions matter more than trying to justify actions by religion.

I discovered this via a HN comment and I can't recommend it enough.

Here's a quote:

1508. The Italian territories destabilized by the Borgias are ripe for conquest. Everyone in Europe wants to go to war with everyone else and Italy will be the biggest battlefield. Machaivelli’s job now is to figure out who to ally with, and who to bribe. If he can’t predict the sides there’s no way to know where Florence should commit its precious resources. How will it fall out? Will Tudor claims on the French throne drive England to ally with Spain against France? Or will French and Spanish rival claims to Southern Italy lead France to recruit England against the houses of Aragon and Habsburg? Will the Holy Roman Emperor try to seize Milan from the French? Will the Ottomans ally with France to seize and divide the Spanish holdings in the Mediterranean? Will the Swiss finally wake up and notice that they have all the best armies in Europe and could conquer whatever the heck they wanted if they tried? (Seriously, Machiavelli spends a lot of time worrying about this possibility.) All the ambassadors from the great kingdoms and empires meet, and Machiavelli spends frantic months exchanging letters with colleagues evaluating the psychology of every prince, what each has to gain, to lose, to prove. He comes up with several probable scenarios and begins preparations. At last a courier rushes in with the news. The day has come. The alliance has formed. It is: everyone joins forces to attack Venice.

O_O ????????

Conclusion: must invent Modern Political Science.

I am being only slightly facetious. The War of the League of Cambrai is the least comprehensible war I’ve ever studied. Everyone switches sides at least twice, and what begins with the pope calling on everyone to attack Venice ends with Venice defending the pope against everyone.

[1] https://www.exurbe.com/machiavelli-s-p-q-f/