Cesare Borgia seated with Machiavelli. From the collections of the Library of Congress.

James Sherry’s The Oligarch (Palgrave Macmillian) uses the twenty-six chapter structure of Machiavelli’s The Prince as the frame to discuss contemporary issues of governance, freedom, stability and personal responsibility. In place of Cyrus, Romulus, and Theseus, James Sherry brings to the page Ross Perot, Jennifer Holmgren, Steve Jobs and Michael Bloomberg. Machiavelli’s work (to quote the Penguin Classics edition) is “a treatise on statecraft,” while Sherry’s new book might serve as the perfect guidebook for today’s aspiring super-entrepreneur. Reading Machiavelli or Sherry is an uphill experience—to borrow a phrase my grade school teacher often used to describe certain books—as opposed to maybe a good detective novel or celebrity memoir, which would be a downhill experience, and also not nearly as timely.

James Sherry is a poet, editor, publisher and author of over twelve books that variously provoke thought in the realms of poetry, prose, literary criticism and environmentalism. In this interview, we take on Machiavelli’s writing style, conspiracy theories, and Adam Curtis’s films on the ecology movement.

Ben Tripp for Guernica

Guernica: What initially drew you to The Prince?

James Sherry: I studied The Prince in college. At that time, I was absorbed by the usual questions about Machiavelli’s seriousness and whether he supported princes and aristocracy or was really an ironic republican. Prior to the Medici taking over Florence, Machiavelli was secretary of the Second Chancery where he coordinated relations with Florence’s territorial possessions. So our professor always stressed how clearly Machiavelli’s personal perspective did not support the prince’s party. We concluded then that Machiavelli was satirical.

When Trump and the other Republican candidates began debating in their primary race, I recalled The Prince. Something new was clearly happening; the relationship between aesthetics and politics in America had changed. Reading The Prince again, in two English versions and through many pages of the Italian as part of writing The Oligarch, I was struck by the complexity of Machiavelli’s motives. The notion that he had a single point of view seemed naïve. When the Medici took over Florence, ending the Republic, Machiavelli was recalled from his post and tortured by Medici henchmen. He was later released to his country farm where he spent the next years writing The Prince. Now it seems that The Prince was also a job application. And, in fact, after submitting the text, Giulio Cardinal de Medici commissioned him to write The History of Florence.

The notion that Machiavelli wrote from any single perspective is exactly the kind of idealism that he was writing against. And in practice we all know that we think and look at our surroundings from many different points of view and cannot easily separate our motives from our actions (except often to our dismay). I should add that the structure of The Prince also attracted me because its twenty-six chapters offered a more complete view than the way journalism and academic papers focused on only one or two issues.

Guernica: Even people who haven’t read The Prince have probably heard the term “Machiavellian” before, often in reference to business or political dealings. Do you think your book could function as a guidebook for today’s young aspiring super-entrepreneur?

James Sherry: I wrote The Oligarch with several audiences in mind, including leadership, the rising aspirants and citizens concerned with politics in our nations. The Oligarch suggests that adopting its multi-perspectival model would force many potential leaders to understand that their successes are not due entirely to their own skills and exertions. Rather all of our efforts, including poetry, must be understood as the result of our individual efforts, and also of our group of friends, conflicts and influences as well as the impact of our surroundings, mental condition and social situation. While there are many other readers addressed, the book is dedicated to Elon Musk but addresses different audiences as it develops.

An environmental model of politics addresses other points of view as well. These perspectives include the different ways we understand the availability of resources. Some people think that there are resources in abundance, some that they should be freely available and others that they are accessible only through skill.  Some think that resources are limited and need to be fought over or that our aspirations should be to reduce our attachment to things. Some people think what happens is a matter of chance. These different perspectives are not owned by people but by the role each takes, my own point of view changing depending on whether I’m a writer seeking publication, a citizen standing at the polling booth, or a tourist in a national park. Conditions, as much as mores, dictate how we view our surroundings. Practically and in my own mind, I have ideals that hardly change, but behavior that changes in different situations. For example, I expect the right of free speech in the public realm while prioritizing respect when speaking to individuals. I wanted these points of view to communicate to various audiences.

In addressing those who do not see themselves as part of the oligarchic network, I hope to show how oligarchs think and act, their aims in different circumstances and their decision process, so that we as citizens do not attribute erroneous motives and characteristics to leaders. If oligarchic methods are made more transparent, we have a greater agency in moving leadership toward supporting other citizens.

Guernica:  Do you find that this archetype of the prince or the oligarch can be somewhat sympathetic at times?

James Sherry: John Milton introduced “Sympathy for the Devil” in Paradise Lost. What we can gain from these cultural artifacts, including The Oligarch, is a comparative point of view, not a bible of literal truth or a roadmap to perfection. The notion of archetypal leadership is only partly valid: conditions and surroundings dominate how leaders behave, yet leaders apply similar solutions through history.

Leadership is magnetic as power is aphrodisiacal, but lest we become enamored of these leaders because we identify with them, The Oligarch tries to humanize them so we don’t see them as ideals to be emulated or hated. Plenty of people have stepped down from positions of power from Japanese emperors to the children of European dynasties. Plenty of people are generous in positions of power like Warren Buffet or Good King Wenceslas. There’s a whole chapter about generosity in The Prince that I transposed to The Oligarch that I found funny when I reread it.

I can’t really support your assumption behind this question, because it treats all the different ways people get to power as part of a single process. I notice how Trump’s irrational discourse has begun to permeate the public discussion of governance. He acts differently than other American leaders. Then the press wants to show similar behavior from other leaders to normalize Trump’s. Many countries today are suffering through kleptocracies. It’s important to present a viable, alternative way to speak about these issues, so that the very attractive hyperbole from both Trump and the media are not the only available discourse.

Disinformation about leadership is as old as agricultural civilization. Carrying leadership’s distorted presentations of itself and reality into our own plans makes it much harder for citizens to achieve personal and collective goals. Understanding the multiple motives in a leader’s network is critical to effective counter-measures. For example, is Jerome Powell, the new Federal Reserve Chair, a creature of the Koch brothers, no? Is the presence of many senior military leaders in Trump’s administration a sign of a coup d’état, no? Where do each of the oligarchic networks with their fingers in the administration’s pie have representatives in the Cabinet or in other important posts? Very interesting question!

Guernica: Do you find Machiavelli to be a sympathetic character? How has his original message been perverted or distorted over the years?

James Sherry: Machiavelli was a person of his times, and a person in 1500 was quite a different thing from a person today. I’m in the middle of writing a new book called Selfie about identity and the environment, so I will say more about this subject there. Also, I am interested in his writing more than his character; they can be separated. In general, I try not to identify with dead people; it’s my superstition. Further I don’t want to try to validate myself by elevating or attacking Machiavelli as a person. He was born to the rising middle class and, while not rich, was never fully dependent on his public income; he had four children; he had one wife and had affairs with other women.

In those days, Italy was a pawn of foreign powers; the state of the state was a mess almost everywhere, and people often opined for a less chaotic society. Look how sad people have become with a year of Trump’s dislocation of civil discourse, and talk isn’t action. Imagine how we would feel if today, New York was taken over by Canadians and Alabama by Mexicans. Then next year, the French prime minister sent an army to lower Manhattan, and the Venezuelans invaded Florida. That was the kind of society Machiavelli lived in, but his expectations were different, so my comparison is problematic. Machiavelli was a political operative in a disorderly society. How many twists and turns did it require to stay alive?

Guernica: The Oligarch is a work of appropriation. Can you talk about the particular ethics of this kind of writing as opposed to more “traditional” modes?

James Sherry: The Romantic notion of what you call “traditional modes,” that an author creates poetry alone, isn’t quite the way I look at writing. I’m in my room, surrounded by other people’s writing—books, magazines, daily papers, websites and manuscripts. My mind is crowded with conversations between people, poetry that I’ve read and poetry that I’ve heard at the Segue Reading Series. I remember other poems that suddenly appear in my mind, a phrase from Blake or Martin Luther King. My own impulses and language informed by a lifetime of other inputs as well as the consolidation of the moment barge their way in or insinuate themselves into my existing cache. My work room is quite packed, from mind to matter, with influences, friends and antagonists. I am far from alone in writing.

The Oligarch is far from radical appropriation. It is a careful update of a significant work that itself appropriates from Livy and other classical sources. The Oligarch includes citation from Machiavelli and Winters, references to other works of political theory, discussion of different ideas of politics from theory to journalism, translations from other genres and disciplines of thought, relationships to similar modes of writing and a couple of potentially innovative ideas like comparing the value of forms of governance to operations that haven’t been widely discussed in this context. In other words, The Oligarch establishes an entire ecosystem of reference, mostly in the realm of politics but also from biology, ecology, psychology and even poetry. Finally, I tried to style these inputs together, but often the seams show.

Conceptualism, as we have used it since the 1970s, is not simply to demean or extoll the source or to toss the relationship between motive and action out the window. The Oligarch marks my choice not to appropriate or imitate mockingly those with lesser privilege than the author, but rather to question those in the high castle. And I’ve been doing this for decades. One of the pieces in Oops! Environmental Poetics (2013) rewrites a biology text into a poetry text by word substitution. Years ago, I wrote a poem derived from a nineteenth century song in “She’ll Be Comin’ Round” (Part Songs, 1978) to connect popular and high art. And many of other writers from the period from language writers to conceptual artists showed how creative work is a collaboration between prior writing and our own efforts.

Guernica: What do you think of Machiavelli as a literary stylist? You say he wrote The Prince as a kind of job application. He also wrote plays. What do you think of his other work?

James Sherry: My Italian isn’t that strong, but Machiavelli’s writing style is a marvel. His winding, hypotactic sentences have an emotional impact beyond semantics. To take an extreme position, I’d suggest a stylistic relationship between his sentence structure and late Romantic novelists. Another acclaimed prose stylist, Richard Hooker, wrote Laws of Ecclesiastical Polity fifty years after The Prince and exhibits a similar prose complexity, but lacks Machiavelli’s roundness and elegance. Most of the recent translations attempt to break up his semicolons in to separate sentences, and I have mostly done that, transforming sentences into shorter more modern periods. Yet, despite his winding sentences, Machiavelli’s diction is discrete, accurate and spare. Most readers of my simplified sentence structure still think in this age of Hemingway and popular journalism that The Oligarch is too dense. Machiavelli is even denser in the original and alternately nuanced, witty, serious, and viciously realistic in the space of a sentence.

Guernica: Adam Curtis’s three-part television opus All Watched Over By Machines of Loving Grace explores how the ecology movement was nearly co-opted by computer scientists; they wanted to render nature as a system just like a computer, or the stock market. Have you seen Adam Curtis’s films? Someone wrote a review recently of The Oligarch in Money Week (the UK’s widest-read financial magazine) where they say your book “verges on conspiracy theory,” which reminds me of those films.

James Sherry: Accusing writers of conspiracy theories is a standard method that financial media outlets use to confuse analysis of how elites extract surplus from societies. But what does conspiracy mean in this case, when there are many different ideas of conspiracy—legal, social and psychological? There have been proven conspiracies to rig prices of LIBOR rates (Barclay’s Bank), dairy (Sainsbury), commodities (Enron) and semiconductors (Samsung). There have been plans to overthrow governments that have failed (Brutus & Cassius) and some that succeeded (Pinochet in Chile and Bonaparte in France). There are more complex and sophisticated ways to control outcomes such as passing laws that are biased against or in favor of certain classes of citizens.

The processes of business have long been suspect. As Adam Smith wrote in Wealth of Nations, “To widen the market and to narrow the competition, is always the interest of the dealers… It comes from an order of men, whose interest is never exactly the same with that of the public, who have generally an interest to deceive and even oppress the public, and who accordingly have, upon many occasions, both deceived and oppressed it.”

I haven’t seen Curtis’ documentaries. The question you raise that interests me is the systems analysis question that he raises and your apparent worry about treating nature as a system. To really answer this question, which I won’t quite be able to do, I need to go beyond politics and treat human activity environmentally, that is, from multiple perspectives. To clarify how humanity and environment are parts of a single complex entity, I found it necessary to deflate the image of people projected by humanism. If we treat humans as part of the biosphere, human minds and actions must be governed similarly to other parts of the planet. Our uniqueness is modified by common processes of the biosphere. And complex entities follow similar mathematics whether they be human or non-human. It’s reassuring to know that others face similar difficulties and that the answers to many of our most thorny problems already exist in other parts of the biosphere: cures for illnesses in rain forests, unlimited energy in capturing sunlight, and more complex organization of all societies to accommodate larger populations.

Ben Tripp

Ben Tripp's writing has appeared in The Brooklyn Rail, HTML Giant, and BOMB.

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