Frank Heijdenrijk ♛
13 min readJun 15, 2023

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15 Books About Machiavelli That Will Transform You Into A Master Strategist

What truly captures the essence of Machiavelli’s teachings?

Picture yourself in the heart of a growing city-state during the Renaissance period. Fountains gushing with water, musicians playing intricate melodies, and artists painting scenes of unmatched beauty all around you. At the center of it all, the city’s ruler sits on a throne, mulling over important decisions that could affect the fate of the entire region.

In a nearby room, a cunning advisor whispers carefully crafted words into the ear of the ruler, offering guidance and strategy in the complex game of power and politics. This advisor is well-versed in the teachings of a certain Italian diplomat and philosopher, Niccolò Machiavelli.

Photo by Marius Teodorescu on Unsplash

Machiavelli’s ideas and strategies have traveled far and wide, seeping into the consciousness of people online and offline, shaping the way many leaders, politicians, and thinkers approach their respective situations. Being proficient in the Machiavellian style of leadership can bring numerous benefits:

  • becoming an effective and persuasive leader (both in-person and online)
  • commanding the attention and respect of those around you
  • conveying your message with clarity and assuredness
  • authoring profound works on politics, strategy, or leadership
  • (silencing your uninformed friends or colleagues during heated debates at social gatherings)

To grasp the teachings of Machiavelli, one must delve into the wealth of literature on his philosophy. I have read hundreds of books over the years, including several works that focus on the ideas of this influential thinker.

I have compiled a list of 15 essential books that you should read if you want to fully understand and embrace the Machiavellian way of thinking.

1. The Prince (Reader’s Library Classics)

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I recommend this book because it is a remarkable guide of governance for autocrats. The Prince by Niccolò Machiavelli emphasizes the significance of utilizing deception and manipulation to govern effectively. It highlights that a ruler must be a fox in identifying issues and a lion in combating them. Machiavelli’s concept of the end justifying the means is dominant in this classic work, and the book is a valuable resource for understanding why autocrats pursue such methods, even if they are wicked and cruel. Overall, The Prince is an intriguing read for those interested in politics and governance.

Check out The Prince (Reader’s Library Classics)

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2. The Prince | Niccolò Machiavelli

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I recommend this because The Prince by Niccolò Machiavelli is a fascinating read for anyone interested in politics. Machiavelli presents a timeless argument that the ends can justify the means. This 16th-century treatise serves as an instruction guide for new princes and royals, emphasizing the importance of survival and glory. Although some may find its acceptance of immoral means to achieve those ends alarming, the book’s themes are still relevant today and can provoke thought-provoking discussions. Overall, The Prince is an essential read that offers insight into the complex and often ruthless world of politics.

Check out The Prince | Niccolò Machiavelli

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3. The Essential Writings of Machiavelli: The Prince, The Art of War, The Discourses on Livy, History of Florence.

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I recommend this extraordinary collection because it brings together four incredible books by Niccolò Machiavelli, an Italian Renaissance diplomat, philosopher, and writer, who is well-known for his book called The Prince. He has been called the father of modern political philosophy or political science. Machiavelli’s writing brings to light the political battles that have been fought with deception, treachery, and crime. He writes about such wars without any morality, considering them as a board game with established rules. The Prince caused a mixed reaction when it was published in 1532, with some considering it a straightforward description of “the evil means used by bad rulers,” while others found it to be a guide to help tyrants maintain their power. If you are someone who is interested in politics, then this is an incredible read that will surely change the way you think about the world.

Check out The Essential Writings of Machiavelli: The Prince, The Art of War, The Discourses on Livy, History of Florence.

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4. Art of War

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I recommend this book because it is an essential reading for anyone who wants to gain a better understanding of the history and theory of war in the West. Niccolò Machiavelli’s Art of War has been praised by some of the finest military minds in history, and it has even influenced famous figures like Frederick the Great and Napoleon. The book explores the connection between war and politics in Machiavelli’s thought and his treatments of the relationships between them are brilliant. Christopher Lynch’s translation is modern and idiomatic, making the book accessible to readers of all backgrounds. The book covers fundamental military organization and strategy, including how to motivate your soldiers, avoid ambushes, and gain tactical and strategic advantages in various circumstances. Lynch also includes an insightful introduction that covers the historical and political context, sources, influence, and contemporary relevance of the book. Plus, maps, an index of names, and a glossary are included to assist readers in better understanding the text. Overall, I like this book because it provides a unique and in-depth view of war and politics, which helps the reader broaden their perspectives.

Check out Art of War

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5. The Essential Writings of Machiavelli (Modern Library Classics)

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I recommend this book because it offers a comprehensive collection of the essential writings of the great Renaissance thinker, Machiavelli. Peter Constantine’s superb translations stay true to Machiavelli’s brilliantly crafted writings, making them refreshingly accessible. This collection includes essays that have never been translated before, including “A Caution to the Medici” and “The Persecution of Africa.” It also has the complete versions of important works like The Prince, The Mandrake, The Life of Castruccio Castracani, and “Belfagor.” Additionally, it features selections from other works like The Discourses, The Art of War, and Florentine Histories. The book is augmented with vital and concise annotations and cross-references, making it a unique compendium. This one-volume reference is sure to become a standard for Machiavelli’s influential and timeless writings. The translations are not only intelligent but also astonishingly good, which is why this edition belongs in everyone’s library. If you’re looking to gain insights into Machiavelli as a writer and broaden your understanding of his personality, this is the book for you.

Check out The Essential Writings of Machiavelli (Modern Library Classics)

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6. The Prince (A Penguin Classics Hardcover)

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I recommend this because this is a must-have for all the book collectors as well as design enthusiasts out there. The book features a hardcover edition of the classic nonfiction works, including philosophical, political, and psychological ideas that have shaped the world. The book series, specially designed by the award-winning Coralie Bickford-Smith, is an absolute delight to have on one’s shelf. One such classic is Niccolò Machiavelli’s “The Prince.” This masterpiece is a reflection of Machiavelli’s experience as a diplomat in fifteenth-century Florence. The book is a pragmatic guide to understanding how power really works, even today. Parks’s contemporary translation has rendered the original text into a language that is as enlightening and alarming as when it was first written. In his introduction, Parks discusses the background and life of the author and explores the context of the work. With more than 1,500 titles, Penguin Classics is a trustworthy publisher of classic literature, providing authoritative texts, distinguished introductions and notes by scholars, and up-to-date translations by award-winning translators.

Check out The Prince (A Penguin Classics Hardcover)

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7. Machiavelli: The Art of Teaching People What to Fear

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I recommend this book because it sheds light on an unjustly maligned figure in history, Machiavelli, and does an excellent job of showcasing his valuable political insights that are still relevant today. The author, Patrick Boucheron, presents a compelling case for Machiavelli in a series of poignant vignettes that illustrate the philosopher’s significance during tempestuous periods in history. Throughout his life, Machiavelli was disappointed by every statesman he encountered, and this led to his writing of “The Prince.” Although it seems to dissociate political action from morality, it begs the important question of who Machiavelli wrote for — the princes, or those who want to resist them? Through his work, Machiavelli offers profound meditations on popular sovereignty and the idea of “the people,” giving us valuable insights into governance and power. Boucheron expertly brings together Machiavelli’s life and work in an erudite, delightful read that is sure to be a guide in times of crisis.

Check out Machiavelli: The Art of Teaching People What to Fear

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8. The Prince (Reader’s Library Classics)

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I recommend this book because it provides a fascinating glimpse into Machiavelli’s philosophy of leadership. The Prince outlines a set of tactics that autocrats can use to manipulate the masses and maintain their power. Machiavelli’s belief that the end justifies the means is a central theme throughout the book, and his ideas are still relevant today. Although some of Machiavelli’s suggestions may be controversial and even disturbing, his insights into human nature and the strategies of power are hard to ignore. If you’re interested in history, politics, or leadership, The Prince is definitely worth a read.

Check out The Prince (Reader’s Library Classics)

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9. The Prince (Penguin Classics)

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I recommend this book because it is a highly influential work on political power. The Prince by Niccoló Machiavelli is a treatise that shook Europe when it was published due to its advocacy of ruthless tactics for gaining absolute power. Machiavelli used his experience of office under the turbulent Florentine republic to reject traditional values of political theory and create a work that recognizes the complicated and transient nature of political life. The book is concerned not with lofty ideals but with creating a regime that would last, making it the bible of realpolitik. Even today, The Prince still retains its power to both alarm and instruct, and the tough-minded and pragmatic Italian in this edition is perfectly preserved in George Bull’s clear and unambiguous translation. Trust me, this book is a must-have in your bookshelf, and it will provide you with an insightful view on the history of politics.

Check out The Prince (Penguin Classics)

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10. The Prince (Royal Collector’s Edition) (Annotated) (Case Laminate Hardcover with Jacket)

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I recommend this book because Machiavelli’s classic, “The Prince”, is an insightful exploration of the principles that have guided Kings, Emperors, Dukes, and governments for centuries. Machiavelli uses his extensive historical knowledge and experience as a statesman to explain why some leaders have thrived while others have faltered. In each case, he suggests a set of principles that any leader would find difficult to follow, but impossible to ignore. This book has had a profound influence on political thought over the past 500 years and provides an understanding of how world leaders think and why certain decisions are made. If you are politically inclined or interested in the affairs of state, this collector’s edition, complete with a beautiful Victorian inspired dust-jacket, is a must-read.

Check out The Prince (Royal Collector’s Edition) (Annotated) (Case Laminate Hardcover with Jacket)

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11. Machiavelli: On Politics and Power (Restless Classics)

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I highly recommend this book because it is a trenchant edition of Machiavelli’s most powerful works of political philosophy, including The Prince and Discourses on Livy, which are timely and eternal, specifically with the prevalence of Machiavellian politicians in today’s world. The book is a foundational work of modern political philosophy and can be seen as a practical or satirical guide on how to rule, as well as an analysis of ancient Roman history that supports Machiavelli’s beliefs on the merit of a republic. The book is introduced by Jon Lee Anderson, a New Yorker writer and biographer of Che Guevara, who explores how Machiavelli’s outlook on power, politics, war, governance, and ethics has frightening similarities to the current trend toward authoritarianism in global politics. Anyone seeking to understand the psychology and methods of power-hungry leaders, past, and present, must read Machiavelli: On Politics and Power.

Check out Machiavelli: On Politics and Power (Restless Classics)

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12. The Prince

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I recommend this valuable book because ‘The Prince’ is a classic written by Niccolò Machiavelli, an influential philosopher, and statesman. It delves into the politics of power and authority, making it a must-read for students of political science and Renaissance history, as well as anyone interested in leadership studies. The Pocket Edition of this book is conveniently sized, so you can easily carry it in your bag or backpack. This edition’s readability is based on Luigi Ricci’s 1921 translation, making it easy to understand and explore Machiavelli’s timeless wisdom. Born and raised in Florence, Machiavelli gained extensive insights into political leadership while serving as a senior official, and his writings continue to provide valuable insights applicable to various fields, including government operations and corporate strategies. Overall, I like this book and recommend it to anyone interested in learning more about the dynamics of power and politics.

Check out The Prince

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13. The Prince: Second Edition

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I recommend this book because it is the most famous work on politics that still manages to hold relevance and shock readers to this day. While initially criticized as a collection of ominous sayings and an endorsement of tyranny, it has more recently been celebrated as the first scientific portrayal of politics as it is, rather than how it ought to be. Harvey C. Mansfield’s translation, coupled with the extra materials added in this edition, makes it the ultimate version of The Prince- necessary for scholars, students, and anyone interested in the shadowy workings of politics. This revised edition also includes an updated bibliography, a substantial glossary, a thorough introduction, a chronology of Machiavelli’s life, and a map of Italy during Machiavelli’s era. As The Wall Street Journal has remarked, “Of the other available [translations], that of Harvey C. Mansfield makes the necessary compromises between exactness and readability, as well as providing an excellent introduction and notes.” Additionally, Choice magazine has praised Mansfield’s work as “worth acquiring as the best combination of accuracy and readability.” In short, Mansfield approaches Machiavelli with remarkable clarity and caution, earning himself the reputation of Machiavelli’s match.

Check out The Prince: Second Edition

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14. Machiavelli: From Radical to Reactionary (Renaissance Lives)

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I recommend this book because it offers an exceptional insight into Niccolò Machiavelli’s life and works. The author is a leading expert on the subject and provides a comprehensive overview of this pivotal Renaissance philosopher, writer, and historian. While the term “Machiavellian” is often associated with the negative connotations of politics, the author presents a more complex and nuanced portrait of Machiavelli. As a high-ranking Florentine government official and a prolific writer, he produced influential political, military, and historical works. However, Machiavelli was not just a political figure. He was a vernacular poet, first-rank dramatist, and religious radical who challenged the contemporary Catholic Church and Christianity itself. This book explores the different aspects of his life, from championing Florentine popular republicanism to becoming a political radical and conservative. It is a must-read for anyone interested in the father of modern political philosophy and political science.

Check out Machiavelli: From Radical to Reactionary (Renaissance Lives)

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15. The Prince: The Original Classic

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I recommend this book because it is one of the most revolutionary works in the world of leadership literature. Machiavelli’s The Prince is a timeless masterpiece that delivers a bold and practical approach to effective leadership. It is a valuable resource for business leaders, politicians, and managers who aim to make their mark in the world. Despite being written centuries ago, the guide’s simple prose and rational reasoning still resonate with readers today. Moreover, this edition features the introduction by Tom Butler-Bowdon, which highlights the book’s relevance to modern-day leadership challenges. So, if you’re looking to enhance your leadership skills and learn from one of the greatest minds of all time, The Prince is a must-read book.

Check out The Prince: The Original Classic

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16. Nicolo Machiavelli The Complete Collection: (4 Books) The Prince, The Art of War, The Discourses on Livy, History of Florence

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I recommend Machiavelli’s works because they are excellent reads that offer valuable insights into politics, history, and philosophy. Each book has a unique focus and approach, leaving the reader with a well-rounded understanding of Machiavelli’s ideas. “The Prince” is a classic political treatise that is both innovative and controversial. “The Art of War” is structured as a dialogue and explores topics such as military discipline and citizen unity. “The Discourses on Livy” uses history to provide lessons for contemporary politics, and “History of Florence” offers Machiavelli’s valuable political experience through the lens of the city’s history. With each book, Machiavelli’s intelligence and insight shine through, making them a must-read for anyone interested in political philosophy or history.

Check out Nicolo Machiavelli The Complete Collection: (4 Books) The Prince, The Art of War, The Discourses on Livy, History of Florence

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Frank Heijdenrijk ♛

Sometimes I believe I have amazing things to write about. Most of the times I am absolutely wrong.