Shakespeare’s Richard III tracks the motives and methods by which one of history’s most notorious tyrants seizes, and then loses, the throne of England. Henry VI, Part III prepares us to understand their significance by showing us the personal reorientation that launches Richard on his career of murder and deceit. Crowning it all is his (anachronistic) promise to “set the murderous Machiavel to school.”

Noting the limits of Richard’s ambitions, and the sloppiness with which he loses his bloody grip on the crown, thoughtful readers have doubted whether he is even a competent student of Niccolo Machiavelli, much less his teacher. Yet, given Shakespeare’s keen interest in the revolutionary impact of Machiavelli’s thought on early modern political societies, as seen in plays from Hamlet to Measure for Measure, it is unlikely that his only explicit reference to the infamous Florentine is a throwaway line.

When we consider the train of thinking by which he conceives of his goal and devises his methods, as well as the reasons for his successes and failures, it becomes clear that Richard has in fact grasped key implications of Machiavelli’s philosophy—especially his views on human nature and its relation to the cosmos—and that fatal errors in Machiavelli’s own understanding are responsible for Richard’s downfall.

As it happens, the side of Machiavelli that Richard best embodies is also the one that has had the most characteristic effect on what is often called the “postmodern” soul. The reasons for Richard’s demise thus constitute a warning about a deadly Machiavellian madness to which contemporary society is highly susceptible.

Richard’s Limited Machiavellian Career

When we first meet Richard, the son of the Duke of York, he is a stalwart if unscrupulous proponent of his family’s cause in the dynastic wars roiling the remains of England’s feudal order. Disappointed by the death of his father and the amatory dithering of his elder brother, Richard embarks on a series of deceitful and violent deeds, including the murder of his own brother, nephews, and wife, by which he briefly gains the throne of England.

Though Richard claims to rival Machiavelli, and is in fact stunningly successful for a time, there are puzzling incongruities between Richard’s character and Machiavelli’s published doctrines.

To begin with, Machiavelli’s greatest heroes are the founders of great civilizations, whom Machiavelli understands as having used a combination of calculated force and ingenious fraud not only to consolidate political power, but also to shape the beliefs of their peoples. Such leaders were revered and obeyed for centuries after their deaths by nations made powerful and hence “happy” by the “orders and modes” they established. Richard, though he will stop at nothing to gain the crown of England, exhibits no interest in what he will do next. And while he is endlessly adept at persuading his future victims to trust him despite the sometimes flagrant evidence of his bad intentions, Richard never constructs the sort of elaborate justification for his actions that might give his future subjects grounds for revering him.

Another puzzling feature of Richard’s Machiavellianism is the series of un-Machiavellian blunders he makes leading to his defeat at Bosworth Field, beginning as soon as he dons the crown. When the Duke of Buckingham balks at carrying out the murder of his young nephews, Richard dismisses him contemptuously, denying him the promised rewards of his prior service. Richard similarly mistreats other allies and needlessly offends several formidable men without depriving them of life or resources. This causes them to defect to his rival the Earl of Richmond—soon to be King Henry VII. When Richard attempts to deceive Queen Elizabeth into supporting his marriage to her daughter, his feeble rationalizations collapse under the weight of her calm reasoning, and she skillfully allows him to think she has consented while proceeding posthaste to marry her daughter to Richmond instead.

Even as we witness Richard’s intellectual powers waning, he impatiently declaims against reason and places his hopes in the employment of desperate force. He dies amid a battle fury in which he admits he has staked his hard-won gains on “the hazard of the die.” Machiavelli, who teaches princes that Fortune can be conquered with the requisite “virtue,” and that failure is the only sin, would no doubt dismiss Richard as a poor student indeed.

Why then does Shakespeare flag the connection between his Richard and modernity’s most notorious “teacher of evil”?

Richard’s Machiavellian Methods and Motives

Richard’s Machiavellian turn comes at a moment when he realizes that he has no friends—that is, others on whom he can rely to advance shared interests. In response, Richard embraces Machiavelli’s teaching that friends—even one’s own family—exist only to be used (and discarded) for one’s own benefit. Since several of his own kin stand to inherit the throne before him, Richard is obliged to eliminate them if he is to become king. Though committing such heinous acts without being stopped seems impossible, Richard is convinced that the skillful use of ruthless force and cunning hypocrisy will prove sufficient for the acquisition of power.

Consider Richard’s assertion that “conscience is but a word that cowards use.” Richard is able to lie and murder with impunity because he believes that ethics do not matter as long as one succeeds in acquiring what one desires. Feigning morality, often against all credible evidence, Richard manipulates others by flattering their moral pretensions while simultaneously promising them selfish gains such as power, prestige, others’ estates, or revenge against their enemies. In other words, he helps them to rationalize vice for what they believe to be their own profit, while cleverly turning their vice to his own advantage. In this sense, Richard is a brilliant student of Machiavelli, one who seems to have every potential to become, if not another civilizational founder, then at least another Agathocles—a Sicilian soldier who gained and maintained the kingship of Cyprus through murder and deceit, though without a grand justification and hence without posthumous glory.

To understand why Richard fails to achieve at least this Agathoclean degree of Machiavellian excellence and instead descends into a state of subhuman fury, we must examine more carefully his reasons for desiring power in the first place. As it happens, this is a subject on which Machiavelli’s philosophy provides limited guidance.

Throughout The Prince, Machiavelli stresses that success or failure in achieving one’s desires is the only criterion by which they can be judged. Regarding the diversity of desires one might choose to pursue, Machiavelli divides men into those who desire material comfort, security, and pleasure (the people) and those who desire power and glory (the great). As for which we ought to choose, Machiavelli never addresses the question. Though praising and admiring the excellence by which some men establish empires and so become “happy,” Machiavelli also calls a contented populace “happy,” and ridicules as imaginary the classical notion of the good according to which the objective value of competing goals can be weighed. For Machiavelli, everything apart from the will—whether we call it nature, Fortune, or God—is hostile or indifferent to the only thing that matters: the successful satisfaction of human desire. Thus, the selection of which overarching desire to pursue seems to be, apart from pragmatic considerations, wholly arbitrary.

This lesson, only hinted at in Machiavelli, is emphasized in Shakespeare’s portrayal of his imagined student. When fighting for his family, Richard had urged his father to break his vow to refrain from seizing the crown, arguing: “Within [its] circuit is Elysium, / And all that poets feign of bliss and joy.” When deciding on his own Machiavellian course, Richard resolves to “make it [his] heaven to dream upon the crown.” This shift from the crown being heaven to Richard making it his heaven illustrates the most radical implication of Machiavelli’s doctrine: by treating desire as arbitrary, Machiavelli empowers—or burdens—men with the task of determining the ultimate purpose of their existence as a whole.

When There Is No Objective Good, Life Is Reduced to Madness

A Machiavellian might object, with Thomas Hobbes, that there is no greatest good, and that men can live without it. According to the Socratic tradition, however, practical reason itself is grounded in the pursuit of such a good. What it means to act reasonably or humanly is to act for some good, and any particular or contingent good is good only in relation to some ultimate good sought for its own sake. If there is no greatest good, then particular goods are not in fact good, and there is no adequate reason to choose one action rather than another. Practical reason becomes an illusion at best, and human life is reduced to madness.

This problem is partly glimpsed in postmodern philosophy, which posits with Machiavelli and Hobbes the nonexistence of an objective good, while conceding to the Socratics that life is livable for human beings only in light of some ultimate aim. The characteristic postmodern solution is for human beings—whether a great ruler, the ruling class, or each individual—to create their own “values,” “projects,” or ultimate meanings of life. From the Socratic perspective, however, this attempt by man to play God is the equivalent of seeking to ladle the ocean dry. If God and nature can offer humanity no possibility of fulfillment, how will our feeble powers accomplish this feat?

It is precisely his “postmodern” application of Machiavelli’s thought that does Richard in. The proof comes in the midst of his collapse, when Shakespeare allows us to see deeper into Richard’s soul than we did in his daytime soliloquies. Awaking from a nightmare in which he is haunted to the point of despair by the ghosts of those he has slain, Richard’s first impulse is to cry to Jesus for mercy. Eventually, Richard is able to suppress his “coward conscience” once more, but not without a dialogue that reveals the nature of his personal disintegration. Noting that he fears himself, though naturally loving himself, Richard realizes that he also hates himself for his hateful deeds and desires to revenge those deeds on himself. His conscience—far from being a manifestation of cowardice—is in fact the voice of practical reason within him, revealing that he has done no good to himself by committing villainous deeds for the sake of a crown that in itself is neither objectively good nor subjectively satisfying.

As the Socratic tradition argues, human beings by nature love both themselves and the good. Human happiness therefore depends on striving for the good of which one is capable. Disordered deeds set up a conflict between our natural loves of self and of the good, the pain of which can be denied or suppressed but not evaded. Shakespeare shows us that Richard’s attempt to stifle his conscience in an attempt at self-creation is nothing but a Machiavellian madness—one that our postmodern culture would be wise to abandon. If we do not, we run the risk of sharing Richard’s tragic fate.