A sweeping, intense historical thriller starring two of the great minds of Renaissance Italy: Niccolo Machiavelli and Leonardo da Vinci. Based on a real historical mystery, and involving serial murder and a gruesome cat and mouse game at the highest levels of the Church— it was the era of the infamous Borgias—A Most Beautiful Deception is a delicious treat for fans of Umberto Eco, Sarah Dunant, and Elizabeth Kostova.

This brilliant novel is an epic tale exploring the backdrop of the most controversial work of the Italian Renaissance, The Prince. Here, Niccolo Machiavelli,

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A sweeping, intense historical thriller starring two of the great minds of Renaissance Italy: Niccolo Machiavelli and Leonardo da Vinci. Based on a real historical mystery, and involving serial murder and a gruesome cat and mouse game at the highest levels of the Church— it was the era of the infamous Borgias—A Most Beautiful Deception is a delicious treat for fans of Umberto Eco, Sarah Dunant, and Elizabeth Kostova.

This brilliant novel is an epic tale exploring the backdrop of the most controversial work of the Italian Renaissance, The Prince. Here, Niccolo Machiavelli, the great "scientist" of human behaviour becomes, in effect, the first criminal profiler, while his contemporary and sometime colleague, the erratic genius Leonardo da Vinci, brings his observational powers to the increasingly desperate hunt for a brilliant, terrifying serial murderer. Their foil and partner is the exquisite Damiata, scholar and courtesan. All three know their quarry is someone who holds enormous power, both to tear Italy apart, and destroy each of their most beloved dreams. And every thrilling step is based on historical fact.

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  • Doubleday
  • Hardcover
  • September 2012
  • 416 Pages
  • 9780385536318

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About Michael Ennis

Michael Ennis taught art history at the University of Texas, developed museum programs as a Rockefeller Foundation Fellow, and works as an independent curator and consultant. He has won several awards for art criticism, and written for such magazines as Esquire and Architectural Digest, on topics as diverse as business, national defense, and politics. But when people ask him what he does, he only claims to be a writer of historical fiction. His first historical novel, Byzantium, was the true story of a Viking prince exiled to the court of the Byzantine Emperor; his second, The Duchess of Milan, was a Book-of-the-Month Club selection, History Book Club featured selection, had a six-figure mass market sale, and was a bestseller in Italy, where it is still selling. Michael lives in Dallas with his wife, Ellen, a television producer, and their Australian Shepherd, Zoë.


"A true masterpiece… Michael Ennis has poured the knowledge and wisdom of many lifetimes into the exquisite form of a mystery so dark, so labyrinthine. The Malice of Fortune is stunning, terrifying, and utterly mesmerizing. I can honestly say I never fully appreciated the genius of Machiavelli, or the savagery of the Borgias, until now."Ann Fortier, author of Juliet

“Michael Ennis bring the Renaissance alive in this tour-de-force: The Malice of Fortune dishes out a simmering stew, thick with chicanery, bloodshed, dastardly deeds, code-breaking, puzzle-solving, and a cast of characters that includes Leonardo da Vinci, Niccolò Machiavelli, Francesco Guicciardini, Cesare Borgia—and Damiata, the real-life courtesan whose brassiness, brains, and beauty dazzle even her employer and nemesis: the Pope.”Katherine Neville, author of The Eight and The Fire

“For readers who’ve been waiting all these years for the next The Name of the Rose—here it is. Michael Ennis brings a scholar’s mind and a writer’s heart to this beautifully crafted work of Renaissance intrigue that has a rare quality of feeling ancient and modern at the same time. A powerful thinking-man’s thriller.”Glenn Cooper, author of Library of the Dead and Book of Souls

“This is a fascinating novel, filled with extraordinary, well-realized historical characters and a plot that is engrossing and wickedly clever. The Malice of Fortune is an excellent, beautifully researched, and well-written novel that has a fine, fine sense of place. It captured my attention up front and kept me turning the pages to the very end."Douglas Preston, co-author of The Monster of Florence

Discussion Questions

There is a marked consensus among Niccolo Machiavelli’s modern biographers that few men were ever less “Machiavellian” – in the modern sense of the word – than Machiavelli himself; he was an affable, kind-hearted, scrupulously honest public servant with an abiding desire to make the world a better place. When you are introduced to the “real” Machiavelli inThe Malice of Fortune, do you find his character surprising? Did you wait for the next shoe to drop, believing that he was merely deceiving Damiata – and us?

The setting of The Malice of Fortune is remarkably austere compared to the typical treatment of Renaissance Italy; the flat pianura of the Romagna in winter (at a time when winters in Europe were much colder than today) seems almost like the frigid plains of North Dakota. What sort of mood did this setting establish? How did it frame the unfolding of the story? Can you compare The Malice of Fortune to other books with a similarly austere, forbidding setting?

The Malice of Fortune takes place centuries before the terms “psychopath” and “serial killer” enter the lexicon. In fact, even the basic concepts of psychology lie in the distant future; in his belief that human nature can be studied and human behavior anticipated, Niccolo Machiavelli actually lays the foundation for modern psychiatry and psychology. What techniques did Machiavelli use to study human nature? And what Renaissance-era terms and concepts did Machiavelli use, as both a character and narrator, to communicate to his contemporaries psychological concepts that would have been utterly alien to them?

The theme of Fortune as the malicious governess of the world obviously pervades The Malice of Fortune; it is an idea central to The Prince and Machiavelli’s determination to anticipate events, to foresee political crises before they can have catastrophic results. This belief in the tyranny of Fortune arises from the widespread belief among Renaissance-era Italians that their institutions — both the church and the state — had entirely failed, leaving them at the mercy of foreign powers and random events throughout the rest of Europe. In our time, do many people similarly share a loss of faith in ability of our institutions – financial institutions as well as government — to provide a stable society and insure fair opportunity for all? Does Renaissance Italy provide a cautionary tale of the consequences when an entire people no longer believe that they have control over their lives?

How does Leonardo da Vinci view Fortune? Are his efforts to decipher the mysteries of nature also an attempt to impose human understanding — and a measure of control — over the seemingly random forces of nature? How would Leonardo change the world, given the power and resources to do so? Did Cesare Borgia tempt him with the possibility of creating a new civilization? How would the world be different if Leonardo’s ideas had been embraced and carried out by his contemporaries?

Before Leonardo, the human body was seen as an unfathomable mystery; even physicians had little familiarity with the world beneath our skin. Leonardo instead regarded the human body as an immensely complex machine and attempted to understand and describe every intricacy of its functioning. Before Machiavelli, individual human nature was not seen as autonomous; each of us was merely a pawn in a cosmic struggle between God and Satan. Machiavelli instead saw individual human character as immutable and unaffected by any higher or lower power; each of us must take responsibility for his or her own fate. Is both cases, is this what is meant by the “humanism” of the Renaissance? How did this kind of thinking pave the way for centuries of progress and innovation?

Both Machiavelli and Leonardo are extraordinarily keen observers, yet their methods of observations are often at odds. How are they alike? How are they different?

Who would be more interesting to sit down and converse with today, Leonardo or Machiavelli? (Michael Ennis has a very strong opinion on this – which he’ll be glad to share with your group!)

Damiata describes a world in which a woman has three choices — all of which are made for her. The first of these choices, marriage, requires her father’s willingness and ability to pay her prospective husband’s family a suitable dowry, while her future happiness depends on her family’s discerning choice of that husband. The second choice, which was often imposed on women whose fathers could not afford a dowry, was the convent, where the nuns lived in poverty and were all too often sexually abused if not prostituted by the monks, who had a dreadful reputation for wantonness and gluttony. Last was the profession of a prostitute; although it usually led to a short and miserable life, a few ambitious courtesans like Damiata were able to achieve something approaching real independence – including the freedom to enter the highest cultural and intellectual circles. If you lived in Renaissance Italy, which of the three paths would you prefer?

Machiavelli’s devotion to Damiata is based on his extremely romantic nature, little-known among those who have read only The Prince, but an aspect of his character that runs unfailingly throughout all four decades of his personal correspondence. In his letters, Machiavelli writes of love as the highest power and describes ardent and intellectually fulfilling relationships with several courtesans and “actresses.” But if Machiavelli clearly adored women – and eventually became a loving if not entirely faithful husband to Marietta – do you think he also had unrealistic expectations of women? What does it say about him that in the end, his greatest love was Florence?

For all her acquired refinement and erudition, Damiata’s origins are very lowly, and she must conceal the psychological scars of having been used by men – and women – for many years before she was able govern her own fate. Can you cite examples where her rough edges and resentments are showing?

While researching The Malice of Fortune, Michael Ennis not only relied on hundreds of scholarly books, articles, and original documents, but also devoted considerable time to the history of forensic psychology and the evolution of scientific thinking about psychopaths and serial killers. Central to this research was the work of psychologist Dr. Robert Hare, who pioneered the clinical diagnosis of psychopathy. Among the key traits Dr. Hare identified were a glib, manipulative charm; narcissism and grandiose self-importance; a need for constant stimulation and a penchant for risk-taking; and an indifference to the suffering of others, along with an utter lack of remorse. Which of these traits became critical to Machiavelli’s initial belief that he was dealing with a very different sort of murderer?

In researching accounts of individual psychopaths, Michael Ennis was struck by how some “high-functioning” or “organized” psychopaths were able, in effect, to analyze the mental health professionals examining them, discover their vulnerabilities and insecurities, and use these insights to their advantage, in a few cases literally seducing a clinician into aiding an escape (Hannibal Lecter is not entirely a fabrication!). The high-functioning psychopath’s ability to not only convincingly feign emotions he cannot feel, but also to be capable of discerning our loftiest hopes and deepest fears, becomes Machiavelli’s key to finally recognizing the murderer. Why does it take Machiavelli so long to understand the murderer’s signature trait? What finally pushes Machiavelli over the edge – or is Machiavelli really just guessing until the very end, when he can finally hold proof of the murderer’s guilt in his hands? Can you think of examples in our time where gifted individuals have appealed to our loftiest hopes – or deepest fears — only to be exposed as corrupt and entirely self-interested?

The Prince idealizes its role model, Duke Valentino, whom Machiavelli later denounced in more candid, lesser-known writings. Yet Machiavelli also tells us he won’t apologize for The Prince. Why did Machiavelli believe there was redeeming value in making the idealized Valentino an example for posterity?

One of the most important aspects of Machiavelli’s character in The Malice of Fortune is his passionate patriotism for his native Florence, even as he laments the shortsightedness of his fellow citizens and the shortcomings of their government. But do we ever see his patriotism go too far, and lead him to unethical decisions? Is The Prince itself, which is really an appeal for a strong man to step forward and rescue Florence before she loses her autonomy to foreign tyrants, a case of Machiavelli taking his patriotism too far?

Machiavelli writes during the first information revolution, when the printing press allowed books and ideas far wider circulation than did the laborious process of hand-copying. Yet Machiavelli cautions that this innovation is morally neutral, allowing lies to proliferate just as easily as truths. Would he issue the same warning to us, now that the internet and digital technology have brought about a second information revolution, with a similar democratization of knowledge?

In The Malice of Fortune, Machiavelli cautions us that the “new man” he has identified – what we would call a psychopath – has a nature that is particularly suited to attaining and holding political power. This man is able to intuit our deepest fears and hopes, using them to both persuade and deceive us; utterly amoral in seeking his self-aggrandizing objectives, he also has a complete absence of remorse for the consequences of his actions. Some recent research has shown that psychopaths disproportionately occupy the highest offices in businesses and government today. Do you think that this sort of deeply flawed character is all too common among our corporate and political leaders? Why do the rest of us allow such individuals to succeed?

As he began researching The Malice of Fortune, Michael Ennis meticulously examined the documented historical record, seeking answers to several key mysteries that historians have left unsolved for centuries: Why did such an astute, self-interested judge of character as Rodrigo Borgia (Pope Alexander VI) overlook his prodigiously gifted son Cesare, and instead place his considerable ambitions in the hands of a younger, hopelessly inept bastard son, Juan of Gandia? Why did Leonardo da Vinci suddenly abandon Duke Valentino, who alone could have fulfilled his ambitions, at the height of Valentino’s power? And why did Machiavelli elsewhere describe the “hero” of The Prince as a profoundly evil man, using terms of genuine moral outrage? The Malice of Fortune claims to unravel these mysteries – and Michael Ennis bases his conclusions on an exhaustive study of the evidence. Can you think of alternative explanations?

As Michael Ennis observes in his Author’s Note, “Machiavelli’s magnum opus, Discourses on the First Decade of Titus Livy, represented his true political philosophy: An ardent champion of the Florentine republic, Machiavelli preferred the imperfect wisdom of the people to the will of princes and passionately advocated representative government — a radical egalitarianism that would not become a potent political force until the American and French revolutions more than 250 years later. The Prince was, in effect, merely Machiavelli’s plan B: what to do when political prudence has long been disregarded, chaos reigns, and the only choice is between effective or ineffective despotism.” Simply put, for centuries we have misjudged, misrepresented and misunderstood Machiavelli based on an out-of-context interpretation of The Prince. Yet this fundamentally false version of Machiavelli remains one of history’s best-known and most enduringly influential figures. Do you think that the real Machiavelli – the “good” Machiavelli – would have been remembered at all without the notoriety of his plan B? (Certainly Discourses on the First Decade of Titus Livy isn’t as catchy a title as The Prince.) What do you think misunderstanding Machiavelli has cost western civilization, both in actual political turmoil and in generally fostering attitudes of self-interest, amorality and dishonesty? Could Machiavelli, who died with his major works unpublished, possibly have foreseen that the term “Machiavellian” would be ubiquitous in popular discourse five hundred years later? And what would he think of the use to which what he described as “a little study of principalities” has been put by both political and business leaders far removed from his time — and entirely unaware of the intended purpose of The Prince?

Did reading The Malice of Fortune make you want to (re)read The Prince?