To be honest for the western world most of that wisdom is holed up in old Greek and Roman histories. Most of the more strategically brilliant minds I know tended to be reading, among the standards already mentioned, military histories rather than specific strategy/tactics books. So, Tacitus, Xenophon, Thucydides, etc. Another one I really like and think is underrated (because it does have many flaws) is the Hagakure.

I could go on. For example, when thinking about the changing landscape of warfare and politics in a nuclear age, I think you can't find a better book than "The Shield of Achilles" by Phillip Bobbit (if you do let me know). With the latest shift in the military strategy space I suspect lots of Mahan and Corbett are being read right now. It is a mistake to too heavily rely on any of these though.

What I have learned over time is that one does not want to look for a "how to" book by a strategic master, or on any subject so esoteric, but rather to glean tidbits of information that over time open up into novel insights, sometimes only after multiple readings.

On the particular subject of Machiavelli, I think the biggest mistake is to focus on the man himself, instead of the greater power struggles of his day. For example the War of the League of Cambrai is one of the most interesting things in the history of Europe to me, and it's almost never talked about or taught.

“Judging by what I have seen and read that it is not impossible to bring [the military] back to ancient modes and give it some form of past virtue, I decided, so as not to pass these my idle times without doing anything, to write what I understand about the art of war for the satisfaction of those who are lovers of ancient actions” - Machiavelli

Frontinus has a cool little book of military stratagems.

https://en.wikipedia.org/wiki/Strategemata

Scroll down for both Latin and English chapter links.

https://penelope.uchicago.edu/Thayer/E/Roman/Texts/Frontinus...

Edit: someone else asked this question on HN awhile ago, and I just remembered that I have it bookmarked. Some excellent suggestions here:

https://news.ycombinator.com/item?id=456275

Carl von Clausewitz, On War, is regularly cited.

Perhaps Striking Thoughts (quotes by Bruce Lee) or The Book of Five Rings, Miyamoto Musashi, as well?

Machiavelli also wrote a "Discourses on Livy", which mixes politcal philosophy lessons with Roman historical examples.

I'd recommend Plato's "The Republic". "Mencius" (self-titled work by the Confucian philosopher) and maybe Confucius's "Analects" for political philosophy and leadership.

For warfare and strategy, other posters have already said Carl Von Clauswitz's "On War" which is pretty much the gold standard of modern military thought publications so I'm going to reiterate it as a must-read. In particular I would focus on Book I, Chapter 3: "The Genius For War". Slightly less well-known is Alfred T. Mahan's "The Influence of Sea Power Upon History" but that's less about leadership and much more about strategy.

A very modern text on tactical leadership would be HJ Poole's "The Last Hundred Yards: The NCO's Contribution to Warfare" https://www.amazon.com/Last-Hundred-Yards-Contribution-Warfa...

Chanakya and Nana Fadnavis. Chanakya has written "Arthashastra" and "Chanakya Niti". Not sure about Nana.

Comparing Chanakya to the works of Machiavelli is not fair. Chanakya was from priestly class who used the religious belief's of the people to his leverage and overthrow the king who did not accept Brahmin(priest) class is superior to Kings. His writing's is about advocating the class system. In the case of Machiavelli his writings is about the observation's of what qualities both good and bad were required to be a king.

Cardinal Mazarin's "Breviarium Politicorum Secundum Rubricas Mazarinicas" (translated from Latin to French, by Umberto Eco, as the "Bréviaire des politiciens") would be such a book (note that whether it was actually written by Mazarin is a subject of debate).

However I do not know if it was translated in English.

I have a copy of The Art of War which also has The Book of Lord Shang in it:

https://en.wikipedia.org/wiki/The_Book_of_Lord_Shang

I'll rec On War, by Clausewitz

Clausewitz, Lenin

Which one of Lenin's books do you have in mind? I haven't read any personally, but he's not usually referenced with any of the others.

Clausewitz, on the other hand, definitely qualifies, although it's a much longer read.

Not the OP but I can highly recommend Lenin's "What Is to Be Done?" [1], one of the best "no bullshit, no moralising, let's just get things done by seeing things as they really are" books of the "modern" era.

[1] https://en.wikipedia.org/wiki/What_Is_to_Be_Done%3F

Thanks for the link. Interestingly, I grew up in Poland, under Marxism-Leninism, but none of his books were ever pushed on us, so this is somewhat of a surprise for me. I'm going to give it at least a quick scan to get an idea.

Lenin's actual writing was not the message that the regime wanted to be known. Usually, the message that gets regimes in power is not the message that keeps them in power.

Marxism-Leninism was Stalin's etiolation of Lenin's actual thought.