Machiavelli – A Deep Scrutiny of his Philosophy and Tactics

Machiavelli – A Deep Scrutiny of his Philosophy and Tactics


Niccolo Machiavelli.


Probably one of the most highly acclaimed philosophers and political theorists of all time.


Also, one of my greatest influences and a figure that has been referenced, quoted, and misunderstood like few.


But before I initiate my attempt to scrutinize Machiavelli and his philosophy, I want to ask you a question.


When somebody mentions the name Machiavelli, or the terms Machiavellian and Machiavellianism, what is the first thing that comes to your mind?


I assume that you think of words like dark triad, duplicity, and manipulation. Or in a broader context the ability to gain power through deception, insincerity, and abuse of power.


Actually, those are all wrong. They do play a role in the way Machiavelli expressed his political theories, but they all fail to paint an accurate picture of the man.


If there is a word that could accurately describe Machiavelli and his ideas, it is this: Pragmatism.


He was probably the first political theorist that escaped the delusion of idealism and honestly proposed pragmatic solutions and interpretations of government. Apparently, his views were dramatically influenced by the time he lived in and his personal experiences, oftentimes exceeding the threshold of political correctness and blurring the lines between morally right and morally wrong. Nonetheless, they constitute a powerful compendium of knowledge that is shaping the interpretation of power and influence until this very day.


At that point, I want to clarify something. The term Machiavellianism was coined by psychologists Christie and Geis in the 1970s as an attempt to explain the manifestation of power motive by exploiting and manipulating others in a deceitful and unscrupulous fashion.


So, the term Machiavellianism is strictly used in a behavioral context.


In all honesty, psychologists did that in a very irresponsible fashion. As we will see in a bit, Machiavelli was a very pragmatic and strategic philosopher. His views were influenced by the status quo of the time and illuminate his ability to offer exhaustive sentiments regarding political theory. I believe that limiting a man of his magnitude to terms like duplicity and manipulation is unfair, to say the least.


In this article, I am not going to discuss dark triad characteristics and behaviors. I will narrow my analysis to the lessons extrapolated by Machiavelli’s works in an effort to draw a more accurate picture of the man and his views.


History and context


Niccolo di Bernardo dei Machiavelli was born in 1469 in Florence, Italy. His family was descended from the old rulers of Tuscany and they have produced many members that were part of the government of the time.


Florence Coat of Arms

Back then, Italy consisted of many city-states that were usually ruled by different Houses. 1 Florence was among the largest city-states in Europe and was considered one of the wealthiest and most successful. Part of this success should be attributed to the “House of Medici” which was one of the strongest families of the time. The Medici controlled the Medici bank – then Europe’s largest bank – and this allowed them to expand their influence and strategic alliances.


Giovanni di Bicci de’ Medici

In 1494, after a popular revolt, the Medici were expulsed from power and Florence was restored to a republic. It was then that Machiavelli received his first government role as the person responsible for the production of official Florentine government documents.


At this point, it’s quite critical to understand that those were really dark times in Italy. Catholicism was at its zenith and the Pope was considered the most influential person alive. Powerful families had conflicting interests and were constantly trying to get the Church on their side. Any attempt to operate independently and against the will of the catholic regime was opposed and oftentimes brutally subdued.


Niccolo Machiavelli

Machiavelli was part of a government that wanted to liberate Florence from the Medici reign, but that was far from easy. The Medici had a strong alliance with the Pope and their recapture of Florence was a matter of time. From 1494 till 1512, Machiavelli experienced a series of career reversals as he was appointed government roles as a secretary of state, a diplomat, and a military general. His career was quite turbulent and ended sadly in 1512 when he was deprived of office after the Medici won a critical battle 2 that helped them emerge to power once again.


In 1513, the Medici accused Machiavelli of conspiracy against them and had him imprisoned and tortured. After denying involvement, he was released and decided to retire to his estate at Sant’Andrea in Percussina in order to devote himself to studying and writing.


That’s when he completed his seminal works “The Prince” and “Discourses” and that’s when he gained his reputation as a great political theorist and philosopher.


The Prince, 1550 Edition

Now, in order to attempt an objective critique of Machiavelli’s views, we need to properly assess the context of the epoch in which he decided to express such views.


Imagine you are a person who descends from an upper-middle-class family and you get the chance to play an important role in the governance of a strong republic. You are overly analytical, quite strategic and also quite pragmatic. You understand the fragility of human nature and you taste the bitter side of it despite your most courageous attempts to be morally right. You feel weak at the sight of excessive power and you are tortured for being on “the right side of history.” 3


You are clearly affected tremendously by all those events and you start to embrace a more cynical life philosophy. Miles J. Unger, who wrote an interesting book called “Machiavelli: A Biography” in 2011, depicts him in a great way:

“Disappointed in his hopes, burning with unfulfilled ambition, he wrote a pugnacious work that makes a fetish of strength and oozes contempt for anything that smacks of weakness or vacillation.”

Moreover, the great thing about Machiavelli is that, compared to other political theorists who didn’t partake in the political sphere and could only focus on “ideal” and sometimes impractical forms of governance, he was deeply engaged in political life for almost 20 years. Therefore, his views resemble a more holistic understanding of politics and power.


Based on those facts, I will try to analyze some very insightful ideas drawn from his most famous treatise, “The Prince.” More specifically, I will focus on five important ideas explained in the book. The trick in order to deeply fathom the underlying principles of those ideas is to open your mind and disassociate yourself from what you consider immoral or politically incorrect.


Machiavelli and his tactics


1. It’s better to be feared than to be loved


When Machiavelli turned to the question of whether it was better for a prince to be loved or feared (Chapter 17 of “The Prince”), he stated that while it would be wonderful for a leader to be both, he should eventually side with fear.


Let’s just pause and reflect on that statement for a second.


I want to believe that the automatic response of a morally sane person to that statement is resistance. Why would you embrace such a paradoxical stance when you know that love should always be the end goal in any mature relationship?


Machiavelli suggests that human nature is somewhat ungrateful, fickle and dissembling. The prince (or any person in power) is like the authority figure that substitutes the parent figure when a person enters adulthood. 4 People in power will always have a huge responsibility towards their followers. This responsibility creates a form of dependency that urges people to keep craving more and hold the prince accountable for most of their needs.


Such an intense interplay damages most of the ability to cultivate self-reliance and people, instead of appreciating the prince’s offerings, breed leech-like characteristics.


Therefore, a prince needs to resemble characteristics that don’t allow others to question his authority. Such a characteristic is fear. Fear, although it still creates a dependency between the ruler and the people, it successfully prevents unwanted behaviors stemming from lack of appreciation.


The trick here is to ensure that fear doesn’t turn into hatred. Intense, cruel and unjustified demonstrations of fear can never keep people engaged. Fear needs to be subtly induced in a way that people can justify it. Events of punishment should be subject to convincing reasoning, for people will side with the most persuasive argument.


2. Reputation is everything but it also demands acting


In Chapter 15 of “The Prince,” Machiavelli states the following:

“Men have imagined republics and principalities that never really existed at all. Yet the way men live is so far removed from the way they ought to live that anyone who abandons what is for what should be pursues his downfall rather than his preservation; for a man who strives after goodness in all his acts is sure to come to ruin, since there are so many men who are not good.”

In this passage, Machiavelli exudes the totality of his pragmatic ideals. He exposes the duplicity of human nature and explains that being constantly nice will get you nowhere because most people are not that nice.


In short, he tries to explain that a prince should destroy the delusion that acting good will always favor him, but at the same time create the illusion that he is actually good, for people respect goodness.


In general, some personal characteristics will earn people praise, others condemnation. Courage, compassion, faith, craftiness, and generosity number among the qualities that receive praise. Cowardice, cruelty, stubbornness, and miserliness are usually met with condemnation. Ideally, a prince would possess all the qualities deemed “good” by others. But this expectation is unrealistic. A prince’s first job is to safeguard the state, and alas, harboring “bad” characteristics is sometimes necessary for this end.


Apropos, while exhibiting these “bad” characteristics, he should do so in a way that projects that the “necessary evil” is employed for the good of the people. His reputation depends on how effectively and subtly he communicates this. Hedging that reputation should be the most important of his concerns.


Side note: Machiavelli also suggests that if a prince decides on many reforms that are unfavorable for the people, he should impose them all together and in a short period of time. After that, he should always try to make things better gradually in order to win people’s approval again. As a rule of thumb, people in power should have in mind this: Offer “good” in small bites, and impose “bad” measures in big chunks and quickly.


3. People are not ready for the truth


Honesty has always been a very crucial element of a congruent and respectable character. When it comes to leadership and politics, though, it will get you so far.


The relationship between the prince and the people is quite a turbulent one. People demand actions, but at the same time, they are not ready to react maturely to difficult situations.


In order to understand the impact this dynamic has in the relationship, we need to work with an analogy. Think of a difficult romantic relationship you had. After the honeymoon face, reality hits you hard and most times one of the parties will let their mask of sanity slip. 5 False expectations, neurotic reactions, unmet needs, and increased familiarity will lead to friction and an inability to maintain a stable connection.



Despite your most courageous attempts to be honest, your partner keeps reacting negatively to news that don’t suit their liking. Your ability to communicate honest views decreases with time and inevitably you become dishonest in order to avoid conflict.


In a romantic relationship, usually, you have the luxury to leave, but a prince doesn’t wish to abandon his position. He decides to embrace dishonesty as the most effective weapon to deal with lack of conflict.


People will almost always favor a delusional hope to a harsh truth.


4. Loyalty needs to be constantly scrutinized and bought and resistance to be crushed


In Chapters 6-9 of “The Prince,” Machiavelli proposes four different ways a prince can rise to power.


  • By virtue – When a prince rises to power through his own skill and resources.
  • By fortune – When a prince comes to power through luck or blessing from powerful figures within the regime.
  • By “criminal virtue” – when a prince rises through cruel, immoral deeds and oftentimes execution of his political rivals.
  • By election – when a prince gets elected by the populace.

Then, he explains what a prince needs to do after he acquires his position depending on the way he ascended to power.


The overarching theme of this idea is that loyalty needs to be constantly scrutinized and bought and resistance to be crushed.


Loyalty – the people who decide to be on the prince’s side will do so because they can benefit from him and not because they like him. They are bound to the prince and their loyalty is a matter of character and benefits. The prince needs to ensure that the rapacious and overly ambitious shouldn’t be trusted and that the weak-spirited and grateful should be sought after and constantly praised.


That is a subtle but great detail to identify. Overly ambitious people can’t stay loyal for long. They are also thirsty for power and eventually will try and sabotage those above them. In contrast, people who are weak-spirited will always savor their relationship with a prince because it allows them to feel safe and that they belong to his tribe.


Resistance – Resistance is an omnipresent force. That is because people are naturally resistant to change and reform. Especially people who benefited from the old order will resist fiercely. Those need to be crushed on a whim and fast so that the prince can focus on reassuring the followers of the strength of the new order and the benefits that will follow.


Princes who keep the old order around will inevitably need to keep fighting them and that suggests a waste of time, resources, and trust. This is very dangerous for a prince because he can’t waste his resources on many fronts and that’s because it is impossible to satisfy everyone. Therefore, he needs to eliminate distractions and focus most of his efforts and resources to convincing his followers that his is right when they have second thoughts.


5. Success = fortune + free will


In Chapter 25, Machiavelli tries to conclude his ideas with the main strategy to be followed by countries and individuals in order to increase their chances of success.


Free will vs determinism has always been a hot topic among thinkers. Machiavelli’s stance on the matter is again very pragmatic. According to him, success is the point where preparation meets opportunity.


A person cannot control the world, but he can definitely control most of his actions. Through foresight, people can shield themselves against misfortune and self-sabotage.


Moreover, because time changes, a prince needs to adapt and embrace malleable characteristics. On the whole, impetuosity surpasses caution and fortune favors energetic youth over cautious age.


In closing


Machiavellian tactics and strategies might come across as quite caustic and even dangerous for some.


For me, his works are invariably imbued with a sense of awe and they constitute a combustible body of omniscience.


Actually, “The Prince” is suggested in most political science programs around the world as a must-read. This is not by accident. Those principles have been espoused and applied by the most successful political figures of our past and our present.


Knowing and understanding those principles can be a crucial step forward in redressing the balance within ourselves and eventually within our political system.


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In the “30 challenges – 30 days – zero excuses” ebook, at least 10 of the challenges focus on becoming more aware of yourself and your surroundings and also assuming control over your future successes.


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Sources: “The Prince” by Niccolo Machiavelli, “The Prince” Wikipedia entry, “Niccolo Machiavelli” Wikipedia entry, “The Prince” Sparknotes

Adrian Iliopoulos

I am the founder and main contributor at "The Quintessential Mind" - A unique personal blog that offers a holistic approach to self-development. I am striving to create high-quality content by investing in a reality-based form of self-help, informed by a deep understanding of psychology, philosophy and my own personal experiences and social adventures.
Adrian Iliopoulos