Niccolo Machiavelli – the Cunning Critic of Political Reason

Vincent Barnett reveals that there is more to Machiavelli than his notorious reputation.

Customarily, the name ‘Machiavelli’ was a synonym for the devil. The myth of the corrupt immorality of Niccolo Machiavelli (1469-1527) has lasted for many centuries, the description ‘Machiavellian’ being used today for anyone who is seen slyly to manipulate a given situation to their own advantage by means of shrewd political insight. Machiavelli as an individual has been described as aloof, as standing to one side of life ‘with a sarcastic expression continually playing around his mouth and flashing from his eyes’. This reputation is based on Machiavelli’s most famous work, The Prince, which was written in 1513-14.

However, is Machiavelli’s lasting reputation as the philosopher-king of political manipulation really justified? This article re-examines Machiavelli’s work and legacy and comes to some surprising conclusions. It also suggests a number of different ways to interpret Machiavelli’s political ideas.

It must be recognised that The Prince was only a small part of Machiavelli’s literary output. He wrote much more substantial works, such as the Discourses on the First Ten Books of Titus Livius, the Art of War, a History of Florence, and even some plays, poetry and biographical sketches. In many ways these other works were more representative of Machiavelli’s ideas than The Prince. Secondly, it must be understood that Machiavelli’s work was part of the political and national context of a Florentine Republic that is 500 years distant from twenty-first century liberal democracy. Machiavelli’s era was that of the Medici family, of naked conquest by military force, Machiavelli himself being imprisoned and tortured for his beliefs and associations, something that was not at all unusual in this period of European history. Thirdly, Machiavelli’s political thought cannot be comprehended without an understanding of Machiavelli the man, of his personal motivations and experiences, and of his youthful dreams and his eventual professional disappointments.

Machiavelli’s Life and Times

The key aspect of Machiavelli’s life was the fact that he always desired to occupy political office. In 1498 as a young man of 29, Machiavelli obtained a job as secretary to the Second Chancery in Florence, for which he travelled on diplomatic missions to cities within Italy and courts outside of it. He served in this job for 14 years, meeting politicians and statesmen across Europe (people such as Louis XII, the Emperor Maximilian, Cesare Borgia) and gaining experience of the winding ways of power politics. He also gave advice on military tactics, successfully organising infantry forces in specific Italian campaigns and establishing a Florentine militia. However, Florence eventually came under Papal control and (with Venetian help) the Medici were restored as a ruling family; Machiavelli had always supported the Florentine Republic and hence in 1512 he lost his job. He was then arrested and tortured, but eventually exonerated and released. He never returned to political office again.

What could Machiavelli do with his life now that his one vocation was denied to him? He picked up a pen and began to write; it was the closest thing to being in office that he could now experience, the abstract cogitation of a lost political reality, conversing in his imagination with the great leaders of the past. And Machiavelli turned out to be a brilliant writer, his rapier-like mind mercilessly dissecting the behavioural patterns of politicians whom he had witnessed first-hand over many years. It has been suggested that Machiavelli wrote out of resentment, but the emotional forces that drove him were stronger than mere resentment. Bitter passions motivated the searchlight of truth that he swung back upon those who had engineered his political exile. The result was some of most profound and insightful political thinking thus far in the European tradition.

The Prince

With this context kept in mind, let us turn to Machiavelli’s diabolical guide to political statecraft, The Prince. What exactly in The Prince was so dastardly? Well, there is a scathing view of human nature for starters. Machiavelli recommended that ‘a prudent ruler cannot, and must not, honour his word when it places him at a disadvantage … Because men are wretched creatures who would not keep their word to you, you need not keep your word to them’. Machiavelli then recommended that ‘one must know how to colour one’s actions and be a great liar and deceiver’. Further on, Machiavelli explained that a prince who neglected what was actually done by people for what (by rights) should be done was doomed to self-destruction. Someone who always acted virtuously would quickly come to a sticky end among the multitude who were not at all virtuous. Hence the successful political statesman must learn how and when to act in a dishonest and immoral way, and must be much better at acting dishonourably than those around him.

This shocking and (to some commentators) outrageous political realism was what has caused Machiavelli’s tarnished reputation to this day. But in fact Machiavelli claimed only to be characterising how everyone acted in normal life anyway. By implication he acknowledged that it would be much better for society as a whole if everyone acted virtuously; it was just that it was (in Machiavelli’s era at least) not possible to guarantee this form of action from all citizens. Given this hard-nosed reality, there was no point in dissembling about it, as even more human misery would be the result. Hence the princely statesman must use guile and cunning in order to guarantee the success and prosperity of his kingdom and his people, although this would also mean the preservation of the resplendent riches of political office.

Another element of The Prince thought shocking by some commentators was Machiavelli’s practical guide to the conquest of other states, a ‘how to’ manual of maintaining control of foreign lands. Machiavelli recommended administering them either by devastating them totally, and living there in person, or by creating a local oligarchy loyal to your own power base. However, Machiavelli warned that whoever was responsible for creating someone else’s system of power had actually ruined themselves, as the demonstrated mechanism of power creation had elevated the assistant into a potential challenger to the new ruler.

Machiavelli also warned rulers of the transient nature of political support, characterising men as ‘ungrateful, fickle, liars, and deceivers’ who shunned danger and were greedy for profit. Hence they would risk their lives for a ruler when the perceived danger was remote, but when such dangers became much more real they would quickly defect. The solution to this problem was for a ruler to make themselves feared (although not hated), so that there was always a psychological dread of punishment. Execution, if properly justified, was sometimes a necessity in this respect, although only when there was a genuine reason for it.

One further significant component of The Prince was Machiavelli’s categorisation of principalities into hereditary, composite, constitutional and ecclesiastical principalities. Machiavelli defined principalities as having family rulers, with republics being left out of the discussion, presumably because they were less likely to be controlled by prince-like figures. Machiavelli explained how new principalities could be obtained by various means – one’s own arms and military prowess, fortune and foreign support, crime, and constitutional astuteness – yet appeared less concerned with the ethical or human consequences of the various methods that were outlined. For example, if criminal behaviour was accompanied by audacity and courage, then success might be the result.

Machiavelli discussed the example of Agathocles the Sicilian, who had arranged to have the entire senate of Syracuse killed one morning by his soldiers; when they were all dead, Agathocles then seized the government of Syracuse. Machiavelli’s judgement was that such ways could certainly win a prince power, although not glory or true eminence. He consequently distinguished between cruelty used well or badly. Cruelty was used well when it was employed once and for all, to defend personal safety and the good of all citizens; it was used badly when it continued to occur, growing in intensity as time went on, without any specifically focused goal. By implication, whether Agathocles did right or wrong in murdering the entire senate depended on his subsequent actions. If as the new ruler Agathocles brought success and wealth to all of Syracuse, he had done right; if he brought failure and suffering, he had done wrong: thus, in Machiavelli’s view, the ends could justify the means.

Interpreting The Prince

Now that some of Machiavelli’s most infamous ideas have been presented, various interpretations of them and their underlying motivation can be considered. One unusual interpretation comes from the eighteenth-century historian of philosophy William Enfield, who suggested that The Prince was a satire on the unruly and selfish behaviour of political leaders. Enfield declared that, since Machiavelli was an enemy of despotism in his actual conduct, The Prince was intended to ‘pull off the mask from the face of tyranny’. If it really was meant by Machiavelli as a satire, then it has to be the driest, most bitter and most convincing satire ever written, one that has fooled many commentators and leaders alike for centuries. 

Machiavelli’s unusual personality makes this an intriguing possibility. Did he really want us to take at face value the notion that men were always ‘fickle, liars, and deceivers’? He declared that the bond of love was one that all men – ‘wretched creatures that they are’ – broke when it was in their interest to do so. Surely if this was the case, then infants would rarely be raised to adulthood, as their parents would desert them at birth. Was Machiavelli so blind as not to realise this basic human truth? He actually fathered six children, and while it is recorded that he was not the greatest of husbands (he sometimes frequented prostitutes), he did not abandon his wife immediately on child-birth. Hence the notion that such a scathing indictment of the behavioural habits of human kind could only have been meant satirically, as a comment on how political leaders often treated the ruled multitude with contempt. 

Another possibility is that, in writing The Prince, Machiavelli was articulating only what he believed that the then-current rulers wanted to hear, so that he could win back their favour. On this view Machiavelli himself might not have believed everything he wrote in The Prince, but he thought that a cold amoral attitude to politics might impress his superiors, thus leading to his reinstatement in government. If this interpretation is true, then he was being doubly cynical by cynically advocating scheming distrust as a method of government, while not fully believing in it himself. The actual circumstances of the composition of The Prince add weight to this interpretation, in that Machiavelli dedicated it specifically to Lorenzo de Medici. It has also been suggested that he composed it quickly, on deciding to take a break from working on the longer Discourses, this apparently coinciding with a period when a new Pope had recently been installed in Rome and a new leader found for Italy. Did Machiavelli hope through The Prince to influence this new ruler? If so this aim was never actually realised, and Machiavelli died without ever regaining his political position.

The Discourses on Titus Livius 

More perspective on Machiavelli’s political philosophy can be gleaned by examining his Discourses on the First Ten Books of Titus Livius, a much longer and more balanced work than The Prince. In a veiled reference to his own long-standing position, Machiavelli wrote in the Discourses that ‘as superior men in corrupt republics … are generally hated, either from jealousy or the ambition of others, it follows that the preference is given to what common error approves’. This common-denominated process resulted in erroneous opinions governing all deliberative institutions and social groups in periods of relative peace, with preference being given to populist doctrines rather than the general good. The follies of such ignorance were (according to Machiavelli) only exposed in particularly adverse situations, when those who had been shunned through jealousy were suddenly sought out for safety. In another scathing indictment of political leaders, Machiavelli declared that it rarely came to pass that men rose from a low position to a high rank without employing either force or fraud, i.e. that superior talent or ability was never enough to succeed on its own. Of these two methods, cunning and deceit would serve better than force, although a combination of the two was often required. 

However, although the Discourses contained many similar negative characterisations of human conduct as were contained in The Prince, at the end of the work Machiavelli suggested that deceit in the conduct of a war was laudable, yet was detestable in all other things. 

Here the importance of understanding the context that Machiavelli wrote in is revealed. In his times, political conflict often involved a physical component to a much greater extent than is true today, so that much of Machiavelli’s advice related to military campaigns and armed conflicts, even within principalities as well as between them. In contrast, more subtle statements about human nature could also be found in the Discourses, for example that men were very rarely either entirely good or entirely bad, or that the people as a body was courageous, it was only as individuals that they were cowardly. Machiavelli even declared that the people were vastly superior in all that was good and glorious when compared to princes, and that the faults of the people sprang from the faults of their rulers. Thus Machiavelli’s sometime-suppressed republicanism was far easier to detect in the Discourses than in The Prince, adding weight to the view that the latter work was not truly representative of Machiavelli‘s underlying beliefs. 

Finally, it is worth recommending Machiavelli’s pithy aphoristic style of writing to the post-modern reader awash in pretentious meanderings. Machiavelli’s terse declarations are often startling and never less than thoughtful. Readers rarely lose sight of the wise old fox who is boxing with their minds, partly out of an earnest desire to educate but also out of sheer mischievous fun. What wicked subversion will Machiavelli dare to suggest next? And how might he turn this conjectural sedition on its head? Only by reading all of Machiavelli’s works might the answer to this textual gauntlet be found, merely the barest outlines having been presented here. 


Machiavelli’s inspirational legacy has lived on well into the twentieth century as a double-edged sword. The science fiction writer H.G. Wells wrote a political novel entitled The New Machiavelli, Antonio Gramsci attempted to update Machiavelli from a Marxian bent into ‘The Modern Prince’, feminist theorists have created The Princess, and the leaders of both Nazi and Soviet totalitarianism lifted their hats respectfully to the Italian master of realpolitik. In much more recent times the spin-masters of Tony Blair’s New Labour Party might also be seen to owe something to Machiavelli’s treatise on cunning guile, although they would undoubtedly deny any such connection when asked about it in public. 

Perhaps one reason for Machiavelli’s continued reputation as devilish is that he made explicit and even celebrated what we still today acknowledge only in our deepest subconscious, that declarations of virtue and integrity are often grinning masks of deception. However, it is always as well to look beyond the surface appearance of something, to go beyond its initially obvious interpretation, to find the personal and contextual motivation that inspired the ideas under consideration. In his dedication to The Prince Machiavelli declared that ‘to comprehend the nature of the people, one must be a prince, and to comprehend fully the nature of princes one must be an ordinary citizen’. In twenty-first century liberal democracy, perhaps there is a little of the prince in everyone: it is only to be hoped that there is more than a little of the people in today’s princely political elite. 

Questions to Debate

  • Was Machiavelli actually as amoral as his reputation attests?
  • What were Machiavelli's reasons for writing The Prince?
  • Are Machiavelli’s ideas still relevant to the modern age? 

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