Found this via my Facebook friends. Links in bold.
The Dictators Handbook
A guide for understanding the logistics of how to become and maintain yourself as prince, or similar position of power. Learn about the keys to power, who they are in your city, and how to appease and keep them on your side.
Good To Great
A book that should be required for every elder and house head, on how to manage and improve your House. This looks at simple leadership tools that you should use to get and keep the right people, and strategies to improve your group as a whole.
Great by Choice
A book that looks at how to establish and what any group, house, or similar group should focus on. It is another book that addresses leadership requirements and things groups establishing themselves should focus on.
How the Mighty Fall
A book that deals with the common foils and follies of leadership, and the mistakes that can be avoided and how to escape them, for groups vulnerable to capitulating due to bad leadership.
The Way of Men
Deals with gang culture and dynamics, and virtues that those groups should adhear to and idolize. (Disclaimer warning, the book is mildly sexist)
Red Platoon
This is the retelling of a battle in northern Afghanistan from the perspective of a medal of honor winner. It talks about what is necessary when everything goes to shit and sideways, and how to persevere and overcome in the face of total adversity.
The Way of the Scorpion (L5R 1st Edition clan book)
A guide to subty, cunning, and spycraft, among other things, as well as basic underhanded political techniques and ideas.
Tokyo Vice - Jake Adelstein
A Burglar’s Guide to the City
How to view a city and is infrastructure like a burglar and look for ways to exploit and use it in unexpected ways.
The Prince of Thorns Trilogy
Deals with playing a political sociopath, addressing when and how to adhere to the social contract and when to ignore it.
Leviathan
Address the founding principles of the Camarilla and their politics. Understanding this political theory will greatly improve your enjoyment of the Vampire the Masquerade as a setting.
The Godfather
Details out how a Prince, House head, or similar body head should act and surround themselves with dedicated and loyal agents. Also a good guide to basic gang structure and politics.
Red Team: How to Succeed by Thinking like the Enemy
How to analyze and attack your ideas and approach situations by using the concept of the devil advocate.
48 Laws of Power
A thesis on political theory and intrigue, and provides guidance on when and how to exploit various common circumstances.
Game Changer: Game Theory and the Art of Transforming Strategic Situations
Deals with the concept of game theory and how to exploit and analyze a situation in the context of Game theory.
Why Intelligence Fails
Deals with how intelligence gathering and analysis can fail, in the face of willful negligence, target focus, and misinformation.
The Caine Mutiny
Addresses that sometimes doing what seems right in the moment the the face of legal authority, is hard to justify and uphold, when placed against tradition and social norms.
The Art of Deception: controlling the Human Element of Security
Deception, social engineering, and exploitation of the human element as a basic guide.
The Count de monte cristo
How to plan for the long term and deal with social and political repercussions, in a political society.
The great book of amber
politics and backstabbing in a world where everyone lies
Argo
information, exfiltration, how to spy and get away with shit
On Tyranny: Twenty Lessons of the Twentieth Century
A book either excellent as a how-to on political tyranny as well as how to prevent or fight it on a very basic, pragmatic and usable guide level.
Imperial Radch Trilogy
A series set primarily in a post-gender sci-fi Imperium, very rigid and interesting in it’s culture and politics, and set around how revenge and revolution interact with mystery and broader politics.