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The Rise And Fall (And Rise) Of Niccolò Machiavelli

Updated: Sep 26, 2023

According to Machiavelli, the ends always justify the means—no matter how cruel, calculating or immoral those means might be. Tony Soprano and Shakespeare’s Macbeth may be well-known Machiavellian characters, but the man whose name inspired the term, Niccolo Machiavelli, didn’t operate by his own cynical rule book. Rather, when Machiavelli wrote The Prince, his shrewd guidelines to power in the 16th century, he was an exiled statesman angling for a post in the Florentine government. It was his hope that a strong sovereign, as outlined in his writing, could return Florence to its former glory.

Machiavelli’s guide to power was revolutionary in that it described how powerful people succeeded—as he saw it—rather than as one imagined a leader should operate.

Before his exile, Machiavelli had navigated the volatile political environment of 16th-century Italy as a statesman. There were constant power struggles at the time between the city-states of Italy, the Holy Roman Empire, France and Spain.

The Prince

As leaders rapidly rose and fell, Machiavelli observed traits that, he believed, bolstered power and influence. In 1513, after being expelled from political service with the takeover of Florence by the Medici family, Machiavelli penned his outline of what makes an effective leader in The Prince.

Unlike the noble princes portrayed in fairy tales, a successful ruler of a principality, as described in Machiavelli’s writings, is brutal, calculating and, when necessary, utterly immoral.

Because people are “quick to change their nature when they imagine they can improve their lot,” he wrote, a leader must also be shrewd. “The fact is that a man who wants to act virtuously in every way necessarily comes to grief among so many who are not virtuous. Therefore, if a prince wants to maintain his rule he must be prepared not to be virtuous, and to make use of this or not according to need.”

Until Machiavelli’s writing, most philosophers of politics had defined a good leader as humble, moral and honest. Machiavelli shed that notion, saying frankly, “It is better to be feared than loved, if you cannot have both.”

Cruelty can be better than kindness, he argued, explaining that “Making an example of one or two offenders is kinder than being too compassionate, and allowing disorders to develop into murder and chaos which affects the whole community.” Keeping one’s word can also be dangerous, he said, since “experience shows that those who do not keep their word get the better of those who do.”

Moreover, Machiavelli also believed that when leaders are not moral, it’s important they pretend they are to keep up appearances. “A prince must always seem to be very moral, even if he is not,” he wrote.

Fortune and Virtù

Finally, leaders must not rely on luck, Machiavelli wrote, but should shape their own fortune, through charisma, cunning and force. As Machiavelli saw it, there were two main variables in life: fortune and virtù.

Virtù (not virtue) meant bravery, power and the ability to impose one’s own will. Fortune, he wrote, was like a “violent river” that can flood and destroy the earth, but when it is quiet, leaders can use their free will to prepare for and conquer the rough river of fate. An effective leader, Machiavelli wrote, maximizes virtù and minimizes the role of fortune. This way, “fortune favours the brave.”

Cesare Borgia

One of the real-life models Machiavelli took inspiration from when writing The Prince was Cesare Borgia, a crude, brutal and cunning prince of the Papal States whom Machiavelli had observed first-hand. During a visit with Borgia to discuss relations with Florence, Machiavelli witnessed as Borgia lured his enemies to the city of Senigallia with gifts and promises of friendship and then had them all assassinated.

Ultimately, even Borgia would succumb to ill fortune when his father, Pope Alexander VI, became ill and died. Borgia died a few years after the death of his father at the young age of 32.

Despite Borgia’s premature demise, Machiavelli believed that a strong leader like Borgia was just what Florence needed to raise morale, unite the people and raise the city state’s prominence to its former glory.

Impact of The Prince

But Machiavelli would not find an audience for his work before his death and Florence was not restored to its former glory in his lifetime. France, then Spain and Austria, invaded Italy and its warring city-states were unable to defend themselves, leading to nearly 400 years of dominance by outside rulers.

Eventually, The Prince was published in 1532, five years after Machiavelli’s death. Over the centuries that followed, the principles it espoused would trigger outrage as well as admiration and establish Machiavelli as a controversial and revolutionary political thinker.

In 1559, all of Machiavelli’s works were placed on the Catholic church’s “Index of Prohibited Books.” The recently formed Protestant Church also condemned The Prince, and it was banned in Elizabethan England. Nonetheless, the book was widely read, and its author’s name became synonymous with cunning and unscrupulous behaviour.

Machiavelli Quotes

  • “It is not titles that honour men, but men that honour titles.”

  • “Where the willingness is great, the difficulties cannot be great.”

  • “Make mistakes of ambition and not mistakes of sloth. Develop the strength to do bold things, not to suffer.”

  • “Whosoever desires constant success must change his conduct with the times.”

  • “The first method for estimating the intelligence of a ruler is to look at the men he has around him.”

  • “Entrepreneurs are simply those who understand that there is little difference between obstacle and opportunity and are able to turn both to their advantage.”

  • “A sign of intelligence is an awareness of one’s own ignorance.”

  • “Never was anything great achieved without danger.”

  • “A wise ruler should rely on what is under his own control, not on what is under the control of others.”

  • “No enterprise is more likely to succeed than one concealed from the enemy until it is ripe for execution.”

  • “The wise man does at once what the fool does finally.”

  • “Hatred is gained as much by good works as by evil.”

  • “The more sand has escaped from the hourglass of our life, the clearer we should see through it.”

  • “I’m not interested in preserving the status quo; I want to overthrow it.”

  • “Benefits should be conferred gradually; and in that way they will taste better.”

  • “The promise given was a necessity of the past: the word broken is a necessity of the present.”

  • “It is better to act and repent, than not to act and repent.”

  • “It is better to be feared than loved, if you cannot be both.”

  • “He who wishes to be obeyed must know how to command.”

  • “One change always leaves the way open for the establishment of others.”

  • “The lion cannot protect himself from traps, and the fox cannot defend himself from wolves. One must therefore be a fox to recognise traps, and a lion to frighten wolves.”

  • “Everyone sees what you appear to be, few experience what you really are.”

  • “There is no other way to guard yourself against flattery than by making men understand that telling the truth will not offend you.”

  • “Men intrinsically do not trust new things that they have not experienced themselves.”

  • “Men are driven by two principal impulses, either by love or by fear.”

  • “There is nothing as likely to succeed as what the enemy believes you cannot attempt.”

  • "A battle that you win cancels all your mistakes.”

  • “Make no small plans for they have no power to stir the soul.”

  • “Gold will not always get you good soldiers, but good soldiers can get you gold.”

  • “Impetuosity and audacity often achieve what ordinary means fail to achieve.”

  • “Wars begin when you will, but they do not end when you please.”

  • “When fortune wishes to bring mighty events to a successful conclusion, she selects some man of spirit and ability who knows how to seize the opportunity she offers.”

  • “Men are always averse to enterprises in which they foresee difficulties.”

  • “Wisdom consists of knowing how to distinguish the nature of trouble, and in choosing the lesser evil.”

  • “He who would foresee what is to happen should look to what has happened: for all that is has its counterpart in time past.”

  • “The innovator has for enemies all who have done well under the old, and lukewarm defenders in those who may do well under the new.”

  • “Forgiveness proceeds from a generous soul.”

The Art of War

Years after writing The Prince, Machiavelli penned The Art of War, not to be confused with Sun Tzu's book of the same name, a treatise written in the form of a dialogue between a military expert and citizens.

The Art of War discusses the role that citizens have in supporting and using military troops to the citizens' advantage, the role of training and the best use of artillery in disarming one's enemies. Drawing on themes he introduced in The Prince, Machiavelli also notes how deception and intrigue are valuable military strategies.

Machiavellian History

Machiavelli would be blamed for inspiring Henry VIII to defy the pope and seize religious authority for himself. William Shakespeare would cite Machiavelli as “the murderous Machiavel” in Henry VI, and many of his characters would embody Machiavellian traits.

Philosopher Edmund Burke would describe the French Revolution as bearing evidence of the “odious maxims of a Machiavellian policy.” In the 20th century, some would point to Machiavelli as playing a role in the rise of dictators like Adolf Hitler and Joseph Stalin.

Hitler kept a copy of The Prince by his bedside and Stalin was known to have read and annotated his copy of the book. Business leaders have looked to the work as a cutthroat approach to getting ahead, and the book has been called the “Mafia Bible” with gangsters, including John Gotti, quoting from its pages.

Some scholars have questioned whether Machiavelli intended that readers take him at his word. Instead, they propose that The Prince was actually a satirical work and intended as a warning of what could happen if power is left unchecked.

But most take it at face value as a cold-blooded blueprint for how to gain and hold onto power. Francis Bacon, the English statesman-scientist-philosopher, was among those who appreciated Machiavelli’s frank reflections early on, writing in 1605, “We are much beholden to Machiavel and others that write what men do and not what they ought to do.”


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