• Brian Keeler

On Machiavelli, transforming into a verb or an adjective- An essay and book review by Brian Keeler

Updated: May 27

Niccolo Machiavelli is probably on the extreme periphery of most people’s awareness today (if at all) but somehow after more than five hundred years his name can evoke polarizing squabbles and unleash a torrent of controversy. These disputes can have geopolitical results, or moral consequences, along with ethical, spiritual and even artistic influences as well.



The Arno River is shown here flowing under the famous Ponte Vecchio. Machiavelli lived in a house just off this bridge to the left. The bridge and many parts of Florence look very much like they did in Machiavelli's day. This 18" x 24" oil painting was done with students watching.


I’ve known of Machiavelli for many years but only until fairly recently did I delve into knowing more about him through a wonderful biography by Erica Benner that was published in 2017 by Penguin Random House. This book, “Be Like the Fox- Machiavelli’s Life Long Quest for Freedom” wasn’t read until this month, but I am glad I did, as it is a real page turner. I did have a problem with the title at first, as is seems to pander to the stereotype and facile understanding of his name. But I found out that this title refers to a quote of Machiavelli which opens up more depth;


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


Machiavelli must be in the air, as there was an ad in yesterday's New York Times Book Review touting a new biography about Mr. Niccolo Machiavelli. This one by Patrick Bouheron with impressive endorsements including one by a favorite author of mine, Stephen Greenblat.

I have been a student of all things of the renaissance for many years, which has been augmented by 25 years of teaching and traveling in Italy and of course many visits to museums here and in Europe. But my first encounter came surreptitiously or through the back door so to speak. Back in art school, at The York Academy of Arts, one of our illustration teachers gave us an assignment to illustrate various politically charged pronouncements. One was;


No man is justified in doing evil on the grounds of expediency.”


Virgil Sova, a faculty member at the York Academy of Arts gave us this project in order for us students to come up with a visually compelling expression of the above quote.

This following quote is from Theodore Roosevelt from 1919 that expresses a similar sentiment, which I would call anti- Machiavellian;


“ The most practical kind of politics is the politics of decency.”


What words could be more relevant today as we are confronted daily with deceit and blame on a gargantuan level and on daily basis from the fellow in the Whitehouse? I am speaking of Donald Trump of course. By contrast, Teddy Roosevelt, quoted above, is speaking for virtue and Machiavelli is advocating (in The Prince) for ruthlessness and despicable conduct no matter what the results. I say this in regards to Machiavelli with a caveat, as we will see later that this reputation as a serpentine advocate of ruthlessness may be a ruse.



A statue of Niccolo Machiavelli in the colonnade in front of the Uffizi Museum in Florence.

When the art school project, mentioned above was assigned, back in 1974-ish, I am pretty sure that I had to look up the definition of expediency. This Roosevelt quote is a close rebuttal to the famous phrase that most scholars of Machiavelli believe that he never actually really said. But he may as well have uttered these words or wrote them in his famous little book, “The Prince.” This little book was actually titled by his editors and published after the author’s death.

But was Machiavelli actually a real Machiavellian? This is the $64,000 question that is bandied about. And most scholars come down firmly with a “no.” Which is rather comforting and reassuring to me. Most of us are troubled with admonitions like “using cruelty well.” So when Machiavelli is seemingly in cahoots with a host of his contemporary tyrants and many other world class despots, who find such suggestions useful, we can only shake our heads in exasperation and disbelief. Such reprobates as Nixon, Stalin, Mussolini and the American sex abuser/rapper Tupak Shakur, to name a few, all found common cause with “The Prince.”

When viewing interviews of our current devotees of Machiavellianism, such as writers, movie producers and politicians we are struck by their rather cold-hearted rationality. A BBC production available on Youtube brought this out. The comparison to the Buddhist principle of Loving kindness reveals an opposition and counter philosophy. I also recall Blanche DuBois’ exclamation at the end of the film “A Street Car Called Desire” that she had “always depended on the kindness of strangers.” Even more illustrative of the perversion and imbalance of including unbridled expediency is an old episode of Star Trek. In that show from the 1960’s, there is a malfunction in the transporter where there is a bifurcation of the crew into their positive and negative personas and it shows a parallel universe of the two extremes. Ultimately we realize that it takes both halves working in concord to be complete. I would venture to say that this incorporation is missing in the current generation of Machiavellians.

While reading this biography by Erica Benner I enjoyed the gritty realism of quattrocento Florence and the intrigue of political life in Italy. But more importantly I could see that most of Macchiavelli's life could be characterized with a desire to transform for the better and to secure some stability to his volatile city and country. He lamented how Italy was dissolute and open to the rapacious invasions of the French, Spanish and Germans. It is my opinion and many others, it is indeed unfortunate that his small manual for despots quickly became his most recognized book. We find this a calamity of fate as his other more thoughtful writings are replete with concern and a desire to improve the lives of his fellows.


A plein air painting of florence as viewed from the hills outside of town near Piazza Michelangelo.Shown here is one of the protective walls that held various invaders at bay during Machiavelli's time.

The life of Machiavelli that is revealed by Benner shows his father, Bernardo to be a kind and considerate man. There is one episode that shows him skillfully negotiating with a cousin of his. This cousin had an affair with Bernardo’s maid that resulted in a pregnancy. Bernardo prevails to show it in his cousin’s best interest to provide a dowry for the girl, even though he denies the episode and blames it on another. These vignettes show a man of principle who can help bring about a positive end to a murky situation. There are many slice of life accounts of Machiavelli’s career brought to us here too. His exile at his family farm in the little town just outside of Florence, called San Casciano includes closely observed details that are endearing. He writes about taking off his dirty work clothes and slipping into elegant robes to converse with the ancients, and they speak back to him as well.

This biography by Erica Benner is a fascinating documentation of a life in the thick of things, taking place in some of the most tumultuous times of Italy. I've read many other accounts of this same era centered around the famous artists in Italy and other movers and shakers like, Lorenzo de Medici and his family, along with Savonarola, Duke Montefeltro of Urbino and many others. The book of Benner’s also strikes a chord as I’ve stood in many of the pivotal spots in the book such as the main square in Florence, the Piazza della Signoria, and other historic points in Pisa, Luca and Bologna.



It is also remarkable how enthralled and steeped in the ancients that all of the educated people were in 15th century Italy. The very essence of humanism was a credo to invoke the wisdom, skill and learning of the brilliant minds of ancient Rome and Greece. Machiavelli’s book “Discourses on Livy” was in fact just that, a mission to learn and apply lessons of the ancients

But back to the rub and conundrum of Machiavelli’s book, The Prince. The content seems to fly in the face of a good part of the social and religious milieu of the time, which is to say the Catholic Church and even the seeking of wisdom from most of the ancient philosophers as well. So how do we reconcile these oppositions? Some supporters of Machiavelli’s Prince would say it is the difference between the ideal and aspirational as compared to life as it is. In a way, it has kind of zen quality to it, as a central tenant of Buddhism is the revelation of life as it is rather than force feeding dogma or imposing of scripture template.



A portrayal of Florence from the Arno River on the western side of the city. Machiavelli's teacher had his school just beyond this bridge on the right next to Ponte Santa Trinita.

A marble bust of Niccolo Machiavelli.

There have been some captivating theories put forth, even by Benner to explain this book and its cringe-inducing suggestions. These justifications center around, well, expediency for one and social engineering for another. It is said that The Prince was just a glorified job application to get him back into his position as diplomat working for the Medici. Benner brings out the fact that the book was utilizing the double edge sword of the ironist to faun poetic to the powers that be, while secretly mocking their duplicity and guile. The Prince is presented as work of seeming concern with effectiveness, while covering his bases with possible escape through shady intentions. It was also observed at the time, that Florentines speak with contradictory phrases, self-preserving contradictions and inherent ambiguity. In a word, the approach of Machiavelli is that of a chameleon, changing colors and dispositions depending on audience and context. So it could be assumed that the perilous impermanence of life seeped into the general demeanor of many and it was not all that particular to Machiavelli. My partner Linda, when she heard my brief summation of Benner’s idea of claiming irony as an explanation for Machiavelli, she warned not to share this with Trump. The DT had just weaseled out of another faux pas by stating that his suggestion of using Clorox to cure covid-19 was merely being sarcastic.

I don’t think we need to worry about Trump joining the Hitler/ Mussolini reading club, as we all know he doesn’t read. He is of course in cahoots with these two as a co-fascist but only by convenience. Some might like to equate the Machiavellians with the DT but we can see that he doesn't even begin to qualify as his methods and results are both nefarious. There is nothing laudable about Trump's goals, methods or means. If there were an altruistic or even an immediately beneficial result to any of of his policies or cabinet members, then in a stretch, some could consider the vileness of his character or the despicable nature of his demeanor somehow worth the cost. But he has not a scintilla integrity no matter the rubric.

The life of Niccolo Machiavelli, by contrast is incredibly rich and varied and we can only admire the breadth of his learning and involvement in a wide range of dangerous missions in government. He even organized a citizen militia to wean Florence away from hiring feckless, fickle, and opportunist mercenary soldiers. His goals were to protect Italy and Florence and to get the peninsula away from the long history of divisive factionalism.

It is another example of the odd twists of fortune and fate that toward the end of his life he experienced his most successful endeavor. He wrote a series of plays, comedies that were performed with great fanfare and huge attendance of all classes of Florentines. Could we say that all of this early work in politics was all just a prequel to the main event of his life- the author of rip roaring parodies of Florentine life? His play, La Mandagoa and others also spoofed on his own life while taking inspiration from the ancient Romans. This was all after enduring a life in the trenches, so to speak, and culminating by the cruel torture, known as the strappado in the Bargello prison.

An excellent “Great Courses” presentation by Professor William Cook titled, “Machiavelli in Context” provided even more thought provoking analysis of this renaissance political theorist. It nicely rounded out this study by giving a very positive take of this man, Machiavelli and his times. Professor Cook lets us know he is not an advocate of mere antiquarianism, which just studying history for collecting facts. He advocates looking at history to draw lesson in the pursuit of wisdom if not virtue.

So Machiavelli has a certain kind of immortality – his name being in use as an adjective since Shakespeare first used it in his play Richard the Third. We could say also, as the title of this essay implies, he has become a verb, an active process and way of thinking. With the meaning of this verb, if I could coin an Italian infinitive, "Machiavelare: to move forward toward freedom." So the take away for me, is at best mixed. Along with a recent BBC production, which showed interviews with contemporary actors and politicians influenced by Niccolo Machiavelli there are many others claiming allegiance to the wily double talking tutelage of The Prince. I think the bottom line however is kind of repulsion from what many have taken away from Niccolo Machiavelli. My wish is that they could see and benefit by his many other good works and be inspired by a desire to improve life.

Brian Keeler painting the Arno River from the Ponte Santa Trinita. Machiavelli's tutor's school was just off this bridge on the south side.

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