The Arrest and Execution of Sir Thomas More in 1535, oil on panel by Antoine Caron; in the Musée de Blois, Blois, France.


DEGREES OF SEPARATION?

MACHIAVELLI, ERASMUS, AND MORE


By Michael Jackson and Damian Grace

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The Montréal Review, December 2025



Few historical figures seem so antipathetic as the saintly Thomas More and the demonic Niccolò Machiavelli. More is venerated in the stained-glass windows of both Protestant and Catholic churches, while Machiavelli is reviled with the devil’s horns on book covers. These polarities have been compounded by subsequent renderings of More the idealist versus Machiavelli the realist, More the humanist versus Machiavelli the reptilian, haloed More the man of principle and horned Machiavelli the man of manipulation, which have cemented these differences into walled cities on distant mountaintops. This ready-made contrast provided Phillippe Bénéton with a lever to insert a third illustrious name into this firmament, Erasmus of Rotterdam, into his fiction, The Kingdom Suffereth Violence: the Machiavelli, Erasmus, and More Correspondence. In these pages Bénéton imagined these three giants of the mind in direct communication – some of it quite vigorous. He set his story not only in a Renaissance context, but also against a backdrop of modern assumptions about Machiavelli, the cynical realist, and More, the protean political idealist. Bénéton's creativity linked them through their contemporary, Erasmus in a three-way exchange of letters. This undiscovered trove lay in a cobweb-ridden archive until Bénéton found it in the attic of his imagination. In historical fact More and Erasmus were friends, housemates at times, and literary agent one for the other, and so exchanged a great many missives. The intruder in the triangle is Machiavelli who, in 1517 according to Bénéton, sent a copy of The Prince to the celebrity intellectual Erasmus who then forwarded it to his BFF More, as he occasionally did with other works like Martin Luther’s Ninety-Five Theses. From that genesis a serious exchange follows about rule, rulers, and ruling. 

Bénéton was inspired to unite these triumvirs because they were contemporaries, though geographically separated. While the historical record is rich for the colloquy of More and Erasmus, in this company Machiavelli is absent, giving Bénéton a free hand.

But wait!  Is there a firmer ground for the constellation of these three stars than Bénéton's rich imagination?  Perhaps there is. 

Consider first just how much More and Machiavelli had in common. Both thrived on the nutrients unleashed by the ferment we now call the Renaissance. During their lives Humanism revived classical antiquity and celebrated human potential and dignity through grammar, rhetoric, poetry, history, Neo-Platonist philosophy, that also flowed into drama, art, music, and practices such as medicine and law. A humanist education became a desirable credential for work in the governments of Italian principalities and republics where it nourished Machiavelli. From Quattrocento Italy humanism streamed northward, producing one its most important scholars, Erasmus of Rotterdam, and one of its most celebrated figures in popular culture to this time, Thomas More. 

More and Machiavelli were active at the same time and worked in a similar milieu. Both had substantial humanist educations, though Machiavelli's humanism has too quickly been discounted and even More's has been subject to recent criticism. They read similar books and served in government. These congruities raise the question of whether by some manner of means they became aware of each other, if not directly, then by word of mouth, intermediaries, or on paper.  How separate were they?

Sociometry is the study of mediated relationships between individuals who are not personally acquainted but have in common mutual friends, work colleagues, neighbourly acquaintances, or removed relatives.  Along these connections we may feel we know a good deal about people we have never met.  While this science can be technical and quantitative, it is illustrated in the film ‘Six Degrees of Separation’ (1993), inspired by Frigyes Karithy’s short story, ‘Chains” (1926), in which inebriated students imagine connections to famous and remote figures through mutual acquaintances, e.g., ‘My Budapest neighbor is Szabo úr who knows the president of the local tennis club who met the tennis-playing King of Sweden when he won a Stockholm tournament. Ergo, I am two degrees from the king.’ Another example from the popular culture is the discussion of ‘connectors’ in Malcolm Gladwell’s The Tipping Point.

With that unit of measure of connection in mind, the question here is how many degrees of separation were there between the Thomas More in London and Niccolò Machiavelli in Florence? Let us consider the following exhibits excavated from the sedimentary layers of history. 

Exhibit 1. 1490s

Englishman Thomas Linacre (1460-1524) travelled extensively in Europe, especially Italy. In the 1490s he went to the University of Paris in pursuit of the New Learning. (This phrase ‘New Learning’ referred initially to Lutheran doctrines, and then to the study of the re-discovered classical texts, especially Greek.) In Florence the de’ Medici family had purchased many such texts and paid for their translation into Latin, making Florence an intellectual magnet because Latin was the pan-European language of learning. Linacre completed medical studies at Padua University near Venice and translated many Greek treatises on medicine into Latin. Linacre's interests were extended to grammar and astronomy. He had in fact gone to Paris both to learn more Greek and to find such works.

During the years Linacre spent in Paris, Desiderius Erasmus arrived; he too was drawn by the promise of the New Learning, and they became acquainted. Linacre and Erasmus would meet again in England in 1498 when this nomad visited there and they become lifelong friends. Additionally, by what Johann Goethe called ‘elective affinities’ in his 1809 novel of that name, Linacre become a close friend of Thomas More, whom he lectured in Greek before he became a royal physician.
A third party entered the Parisian stage when Giampiero Machiavelli arrived for a lengthy stay. William J. Connell has drawn attention to this man, identifying him as a cousin of Niccolò Machiavelli, who lived across the road from the farm where Machiavelli passed his rustic retreat after 1512. (Henceforth, Giampiero will be known by his forename, and Niccolò by his last.) Linacre and Giampiero became friendly during this time in Paris and as late as 1513 they were still in touch by letter. 

Note that in the 1490s Thomas More was a twenty-year-old stripling, while Machiavelli, a decade older, entered government service in 1498. Ergo, it seems unlikely that Linacre would have mentioned the young More to Giampiero, nor that Giampiero would have mentioned the fledgling Machiavelli to either Linacre or Erasmus in these Parisian days.  

Howsoever, this mingling brings More and Machiavelli within two degrees of separation. Machiavelli knew Giampiero who knew Linacre who knew More, and if we add Erasmus a second neural pathway is opened between them.

Exhibit 2. 1506

Erasmus was a perennial gypsy who moved with the ebb and flow of patronage, research grants and visiting professorships. Between 1506-1509 he travelled in Europe as the preceptor for two sons of an English courtier. This sojourn went through Paris and reached a southern terminus in Rome. His personal goal was the antique university of Bologna, which was a hothouse for the New Learning, and with his two charges he resided there for a time. Force majeure intruded, however, when Pope Julius II made war to reassert sovereignty over errant Papal states. Weeks later Erasmus returned to Bologna to witness Pope Julius II’s triumphal entry, as did Agostino Vespucci, who was a friend and confidant of Machiavelli and wrote to him from this juncture. Indeed, Machiavelli lui meme had been earlier with Vespucci in the Papal train, for at this time he was in the middle of his career as trusted agent of the head of the Florentine Republican government, which regarded the ambitions of Julius with suspicion.

By 1506 Erasmus had become something of a celebrity thanks to the 1500 publication of Adages, a collection of words of wit and wisdom from classical Greek and Roman texts at the core of the New Learning. Among these sayings there were those that implied criticisms of priests, religious tyranny, and even popes, all of which would have entertained Machiavelli. Knowing this scribe was at hand, Machiavelli would surely have sought him out as a kindred spirt, an elective affinity, as Goethe had it.

Even if Machiavelli had returned to his Florentine duties without such a meeting, his time in Bologna put him in proximity to Erasmus, again making Machiavelli two degrees separate from More. To wit, in the supercharged political context, it is possible that Vespucci might have mentioned his friend, travelling companion, and fellow Florentine official had he occasion to meet Erasmus who, likewise, might have mentioned his friend Thomas More, who had just begun a political career in England, taking a seat in parliament in 1504.

Exhibit 3. 1506+.

During this stormy period, it is certain that Erasmus was in Florence for the month of November 1506.  Julius II’s war making had convinced Erasmus to decamp from Bologna with his young charges for a safer haven in Florence. There he ensconced himself among the books, scrolls, and manuscripts of the San Marco religious complex, this collection approximating a public library where, inferring from later references to the work he did, suggest a residence for up to six weeks.

In the period 1506-1509, Machiavelli was a busy man, but, when he had time, he read voraciously and must certainly have known of and likely himself used San Marco’s collection. That the literary lion Erasmus was there would have attracted him, but we can only speculate on what might have been. Nothing in the surviving written record indicates they met at this time, or any other. Equally, nothing rules against it. 

Even if they did not meet in the cloister of San Marco, perhaps they consulted the same monk librarian for the location of a tome, bringing them to one degree of separation. What might they have said in Latin, one to the other, there in those solemn confines in the year 1506?  Erasmus was a famous writer and Machiavelli occupied a key role in government. 

Exhibit 4. 1508.

Erasmus, having earlier returned to a peaceful Bologna, went to Rome in 1508 to see the Pope, and then in later 1509, left Rome with his tutees en route to England. To do so he almost certainly travelled through Florence on one if not both ways of this trip, and being a large city, it would have offered more and better accommodation and food than many other smaller settlements along the way. And, of course, as per exhibit 3 he would have been familiar with what Florence offered. Such circumstantial reasoning leads to the conclusion that his party stopped in Florence at least once, if not twice, affording Machiavelli another opportunity to meet Erasmus.

Exhibit 5. 1513.

After Machiavelli’s dismissal in the civic corporate re-organisation in 1512, he composed the manuscript that became The Prince. Since he did not try, and probably never intended, to have it printed, it remained a living text in his hand, and he inserted references to topical events after 1513. Though not printed, The Prince did circulate both on paper and by word of mouth. He discussed it with a circle of others, and copies were made, though who paid for that work and how these copies were disseminated remains unknown. As his biographers note, those who read or heard of the manuscript may have broadcast some word of it to others in the zeitgeist.

Exhibit 6. 1514+.

Finding himself in uncomfortable circumstances in Florence with the confusion following the regime change, in 1514 Giampiero again travelled north, returning to Paris, perhaps drawn by recollection of his more carefree student days. Once there he found a likewise returned Thomas Linacre. It could well be that in rekindling his friendship with Linacre, Giampiero dwelt on recent events in Florence that stimulated his exit, and Linacre with his avid interest in Italy and Italians, as well as his own experience in Henry VIII’s court, could have probed for details. Having a kinsman in the fallen Republican government would have credentialed Giampiero to comment in Linacre’s eyes. Indeed, it would have been unnatural had Giampiero not evoked cousin Machiavelli’s name, position, experience, and observations.

While fiction writer Phillippe Bénéton imagined The Prince transmitted later by letter from Machiavelli to Erasmus to More, the tantalising thought is that Giampiero might have taken along with him a copy of that cousin’s recent manuscript, The Prince. Had he done so, peradventure it made its way, whole or part, in written or oral form, back to More via Linacre who is mentioned three times in the letter of William Budé that prefaced the first editions of Utopia. William Connell has speculated that More might have become aware of at least that passage of chapter 15 of The Prince that refers to the ‘many writers [who] have imagined republics and principalities that have never been seen nor known to exist.’ Connell wonders if that added fuel to More’s motivation to write Utopia. If that happened, then on paper More and Machiavelli were in direct contact. Picture More sitting before a warming hearth hearing Linacre describe the career of Cesare Borgia as distilled by Machiavelli. 

Exhibit 7, 1516.

Erasmus in Louvain acted for Thomas More to have Utopia printed in Latin. This first edition was soon followed by four others in More’s lifetime, printed elsewhere to reach further audiences. This book has some claim to being one of the first European-wide secular best sellers. Its fame travelled as far as Florence we may be sure.

Exhibit 8. 1519.

More and Erasmus had worked together to gather, select, edit, and translate a group of essays, stories, fables, and dialogues by Lucian, a Greek writer, who came to the fore on the tide of the New Learning, including his novella, A True Story, which some scholars say inspired More to write Utopia. While Erasmus was in residence in Venice, he supervised the publication of this compendium by the Aldine Press, one of the most enduring and well-known publishers of the time. Subsequently, a clone of this edition appeared in Florence, printed by the Giunti family, with whom Erasmus evidently was in contact, perhaps through his earlier visit(s) to the Arno, though he was not himself in Florence in 1519.

This Florentine version differed from the Venetian one in one major respect: in addition to Lucian’s little works, added at the end was More’s Utopia. Connell refers to this printing of Utopia as the ‘mysterious edition.’ The mystery is why, and even who chose to, attach Utopia to the Lucian anthology. Connell’s argument, in sum, is that friends of Machiavelli hoped that by showing another writer discussing advice to princes, criticism of Machiavelli would be diluted. That explanation invites a comparative reading of The Prince and Utopia as a litmus test of that conclusion.

In any event this publication is another instance where the intellectual aurae of More and Machiavelli brushed against one another.  The unemployed Machiavelli was at leisure in 1519; certainly, Lucian’s ribald and irreverent humour would have appealed to him. In addition, Machiavelli had earlier translated Lucretius whose doctrines were consonant with Lucian’s. It would seem likely that he might have picked up a copy of this printing, and of course, if his supporters did have a hand in it, they would have called his attention to More’s little work. 

Then the possibility exists, as Connell avers, that Machiavelli read More’s Utopia in that Florentine edition. Francesco Vettori, another of Machiavelli’s patrons, made a dismissive remark about More’s Utopia at this time indicating that it was known to members of Machiavelli’s network. What moves it from a ‘possibility’ along the continuum toward a ‘probability’ is that Machiavelli was friendly with members of the Giunti. It was their firm that printed his own The Art of War in 1521, the only book bearing his name that he himself published. It is easy enough to imagine Machiavelli visiting the business in his retirement and any book with Erasmus’s name on it would have been noteworthy. As he idly turned the pages he might have come upon More’s little book. What would he have made of it? The social criticism of Book I would have elicited nods of the head, as would the description of the foundation of Utopia, while the ordered Utopian society might have reminded him of a cloister not a city.    

Exhibit 9. 1527.

The last layer in this sediment dates from Bologna in March 1527. Once again, marauding forces of mercenaries were at war. A twenty-seven-year-old Englishman Thomas Wyatt (the Elder) (1503-1542) was traveling through Italy with an emissary of Henry VIII who carried valuable letters of credit to the Pope, a sizeable donation which Henry offered in the expectation of reciprocal benefit. In his eagerness to take the waters of the New Learning, with special reference to poetry, Wyatt took leave of his senior colleague and went on alone into the strife-ridden countryside. Wyatt soon discovered his folly when he was taken hostage by German mercenaries who put him up for ransom since their Spanish paymasters were in arrears. In due course he was released and appeared in the camp where Francesco Guicciardini, who was then a general in the Papal army of Clement VII (a Medici scion), saw him. Days earlier the general had been accompanied on campaign by his client, Niccolò Machiavelli.

If Johann Goethe was right and ‘elective affinities’ do bring like-minded people together, then it is tempting to think Wyatt, a courtier, poet, and ‘beloved familiar’ of Henry VIII, who was well known to Thomas More, warmed himself at the same fire as had Machiavelli, who once fancied himself to be a poet.   

If Machiavelli had left by the time Wyatt arrived, then Guicciardini probably encountered Wyatt. If they talked, Wyatt would have credentialed himself as an English agent, and perhaps even, as men sometimes do, especially younger men, made himself seem more important that he was. He might have boasted of his friend Thomas More, then the Chancellor of the Duchy of Lancaster, governing much of northern England. Because Guicciardini disliked English meddling in Italy, he might have probed for information from this callow youth, and in so doing Guicciardini, equally, might well have borne in mind some of the insights of Machiavelli’s The Prince, with which he was certainly familiar, making Machiavelli a ghostly presence at their conversation. No doubt had the occasion arisen later, Guicciardini would have told Machiavelli of this interfering Englishman, because Machiavelli’s surviving personal correspondence evinces his own abiding interest in English intrusions into the Peninsula. And returning to England might not Wyatt have dined out on the story of his captivity and ransom, enhanced by poetic flourishes, within the hearing of More? 

The result is another instance of two degrees of separation: More-Wyatt-Giucciardini-Machiavelli.

Conclusion

The cumulative weight of these exhibits suggests the possibility of a mutual awareness between More and Machiavelli. Of course, the circumstantial evidence does not warrant a conviction, but it does indicate a possibility, if not a probability. William J. Connell has ventured the suggestion that Machiavelli’s derogatory passage on writers who imagine paper republics may have added fuel to More’s determination to compose Utopia. We may never know the truth of this matter, because there are no extant letters, notes, or remarks from the hand of either More in London or Machiavelli in Florence to confirm this supposition. Tant pis. Is that necessarily the last word? 

Letters may certainly be lost only for an intrepid Professor Henry Jones to find them in the most unlikely places but, alas, letters may also perish in time and tide. Energetic and frequent correspondent though Erasmus was, and despite the voluminous epistolary record he bequeathed to posterity, he sometimes destroyed letters, asking his correspondents to do the same to suppress his candid opinions which might upset prospective patrons. Moreover, he was negligent about keeping them in the very years when his friendship with More hatched. Many of More's letters along with his papers have disappeared, possibly because he destroyed them or because they were not returned after his trial, either being burned or eternally misfiled. Machiavelli, assiduous in his official dispatches, was careless in his personal correspondence, and kept none. Those we have today were located, solicited, identified, copied, collected, and in some cases, edited, many years later by one of his grandchildren. Finally, identifying a letter on aging paper, with faded ink shorn of date or even signature can itself be a forensic challenge. Consequently, for all three individuals, there are gaps aplenty in the written remnants which Bénéton filled with imagination.    

What is more, their subsequent fame created a market for their letters, and this demand was sometimes supplied by enterprising forgers. In fact, in their own days fraudulent letters may have been circulated to blacken their names long before internet troll farming. 

These three men were sensitive to the political winds near and far. Earlier Machiavelli had been fascinated by the ascension of the teenage Henry VIII. That meddling in Italy that Guicciardini disliked kept English affairs current in Italy. In London More had innumerable close associations with men like Linacre, Wyatt, and Reginald Pole who had extensive experience in Italy, and with the many Italians both visiting and resident in London.  And the peripatetic Erasmus always had an eye on the horizon.

More and Machiavelli did not meet face-to-face, yet long before the advent of social media they may have had an asymmetrical proto parasocial relationship, as a social scientist might say today. That is, each may have had an awareness of the other without realizing that it was reciprocated. On the balance of possibilities, it is tempting to think so.

The purpose here has not been to settle that matter but rather, being guided by the aphorism that the absence of evidence is not itself evidence of absence, the aim has been to show what might have been and even perhaps was. There is no record of the energy passed along the intersecting ley lines connecting Machiavelli and More via Erasmus, Giampiero, Linacre, or Wyatt, and yet it may have occurred off the stage of historical documentation, but this side of Bénéton’s witty fiction. In short, their networks may have overlapped and intersected more than once. We have presented here some good, if tenuous, reasons to think so. To polarise Machiavelli and More based on dubiously contrasting modern antipathies -- realist/idealist, humanist/practitioner, progressive/conservative, pious/atheist – blinds us to their enduring affinities which would have been apparent to them. This is an argument for another occasion. For the present, it is sufficient to note that such crude divisions have imprisoned two of the most subtle and insightful thinkers behind anachronistic walls of our making, not theirs.

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Damian Grace is an Associate Professor (Retired), University of New South Wales, Sydney, NSW, Australia. Michael Jackson is an Emeritus Professor of Political Theory at the University of Sydney. Their book Machiavelliana was published by Brill in 2018.

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The authors gladly acknowledge the stimulating, creative, and meticulous research of William J. Connell which inspired this jeu d’esprit and the editorial assistance of Kathlyn Blake.

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