To raise the concept of judgment is almost inevitably to raise the name of Aristotle. According to Leo Strauss, Aristotle was “the founder of political science” because he discovered the art of practical judgment.Footnote ³ In the Nicomachean Ethics Aristotle attempted to theorize this art as a form of reasoning appropriate to citizens situated in juries, legislative assemblies, and deliberative bodies of all sorts. He associated it with the man—and for Aristotle it is always a man—who possesses the skills necessary to manage well the affairs of the political community. Like his teacher Plato, Aristotle thought of judgment as a form of knowledge, but unlike Plato he was unwilling to consign it to the shadowy realm of opinion. Judgment is a form of practical reason; that is, deliberation about particular situations, particular events, on particular occasions. Judgment is, for Aristotle, an intellectual virtue and, like all the virtues, it can be taught just like any other skill or craft. Like the joke about the tourist who asks how to get to Carnegie Hall, Aristotle would reply, “practice, practice, practice.”

At the other end of the spectrum is Kant's theory of aesthetic judgment.Footnote ⁴ By aesthetic, Kant meant what the term originally denoted, namely relating to the sense of perception and taste. In the Critique of the Power of Judgment, Kant extended the scope of judgment beyond the spheres of ethics and politics and into the domains of beauty and taste that seem far more personal and subjective. Judgments of taste seek agreement, a kind of sensus communis, but not correctness.Footnote ⁵ Kant described the experience of beauty as falling under the category of “reflective judgment” because it does not involve truth claims but expresses the observer's active engagement with experience. When we say that a particular experience—a piece of music, a painting, a sunset—is beautiful, we are not so much describing some empirical property of the world but rather articulating our own sense of how the experience strikes us. No one can say exactly why something strikes us as beautiful; it just does. Our aesthetic judgments are distinctly noncognitive in the sense that they express the active and synthesizing capacities of the imagination.Footnote ⁶

Berlin is virtually unique among political theorists for giving judgment pride of place in his philosophy.Footnote ⁷ His reading of such “Counter-Enlightenment” figures as Vico and Herder taught him that historical judgment is formed by the ability to imagine ourselves in very different worlds from the one we inhabit.Footnote ⁸Berlin was captivated by this unique human ability that allows us to see ourselves from another's point of view and imagine what it would be like to walk in someone else's shoes. Good judgment in art, as in politics, is the ability to imaginatively project onto the world certain possibilities that no one has seen or previously experienced. It is the kind of capacity we associate not with the scientist who seeks laws and uniformities, but with the artist, the poet, the novelist, and the playwright who seeks patterns and connections between colors, shapes, characters, and words. Berlin's standard for judgment might be described by E. M. Forster's motto, “only connect.” Judgment is an aesthetic apperception, something like the ability to see coherence in a painting or work of art where others see only chaos and confusion. It is not just a quality of the mind but involves the entire personality of the individual.

Berlin's models of good judgment in politics were drawn from the great statesmen of the twentieth-century whom he often described with more than a touch of hero worship. Yet his reading of their statecraft veered between a cognitivist model of judgment as a skill or craft—something that can be learned and imparted—and a noncognitivist model that he often described in terms of aesthetic criteria such as sympathy, intuition, insight, and imagination. My thesis is that Berlin acknowledges the necessity of both these components of judgment but does not sufficiently distinguish between them. At the core of Berlin's theory of judgment are a series of questions like the following: what kind of knowledge does judgment entail? Does it require some kind of philosophical knowledge, immersion in the world of practical experience, or is it an intuitive ability? A crucial question not only for Berlin but for any student of politics is whether good judgment can be taught. Is it a skill that can be learned and imparted or an innate quality possessed only by certain kinds of rare individuals, and, if so, which ones? If judgment is a skill like carpentry or auto repair, it should in principle be teachable, but if it is more like having good taste or possessing a sense of savoir faire, then it is not obvious whether these qualities can be imparted to others. If not, then how are they acquired in the first place? It is this tension that I intend to explore.

Judgment and historical understanding

At the core of Berlin's thinking about judgment is a distinction between the natural sciences and the social sciences (or human sciences). This distinction can be traced back to the German division between the Naturwissenschaften and the Geisteswissenschaften, a point most vividly developed in Berlin's essay “The Divorce between the Sciences and the Humanities.”Footnote ⁹ The title of the essay sounds superficially similar to C. P. Snow's famous lecture series The Two Cultures, which deplored the disappearance of a common culture uniting both the sciences and the humanities, but this is virtually the opposite of Berlin's point.Footnote ¹⁰ For him, the divorce between the two is not only necessary but desirable. The sciences and the humanities employ two radically different vocabularies and any attempt to bridge the gap between them can only produce conceptual confusion. The attempt to find common ground, however well-meaning, will inevitably lead to a blurring of crucial differences and the subordination of one to the other, as the history of the social sciences makes plain. The best we can hope for is an amicable parting of the ways.Footnote ¹¹

The natural sciences are based on three related features: experimentation, replication, and anonymity. A natural experiment is, presumably, one that anyone should in principle be able to replicate and reproduce under laboratory conditions. It seeks to explain not some individual phenomenon but classes or types. The point of the natural sciences is theory construction, to create a body of theoretical models capable of explaining all the relevant facts. Such theories should be in principle anonymous. They should not bear the idiosyncratic traces of the scientist but should be purged of all identifying personal characteristics. It should not in principle make any difference—except for the occasional Nobel Prize or research grant—whose theory it is. The only question is whether it is true or not, whether it is sufficiently explanatory.

The human sciences, by contrast—and Berlin tends to associate this term with historical understanding—rest on an entirely different set of presuppositions. Historical understanding takes its point of departure from the individual, whether a person or an event (an election, a war, a revolution). Its purpose is not to understand revolution as an “instance” or “case” of some general theory of revolutions—although such has been tried—but to understand events in their singularity.Footnote ¹² Historical understanding is necessarily particularizing. The core difference between natural science and historical understanding, however, is that we can understand the latter from the “inside,” as it were. History is made up of persons with ideas, beliefs, desires, intentions, and purposes, in other words, a whole range of mental and emotional attributes that identify them as recognizably human. To understand the past, we must try to enter their world, to think and feel as they did. It would be absurd to ask a natural scientist what it feels like to be a wave crashing on the beach or a planet orbiting a star. Historical understanding is, in short, always a matter of entering the minds of others and trying to imagine the past as they saw it themselves.

Berlin's idea of historical judgment derives in part from the Neapolitan philosopher Giambattista Vico.Footnote ¹³ Vico's principle verum est factum convertuntur—we know the world because we make it—suggests that we understand the human world in a very different way from our understanding of natural objects. Because we have a special insight into our inner lives, this enables us to understand other human beings and their doings more intimately than we do natural phenomena. As Wittgenstein famously said, “If a lion could speak, we could not understand him,” suggesting that the limits of our language set the limits of our imagination.Footnote ¹⁴ We have no idea of what it would be like to be a rock, a plant, or a lion, for that matter, simply because there is no inside there. In fact, the effort to provide a purely external or objective account of human behavior without reference to motives, intentions, or purposes deprives us of one of our crucial human faculties, namely the ability to see others as we see ourselves.

Vico's verum est factum principle was introduced to an English audience by way of R. G. Collingwood's posthumously published The Idea of History.Footnote ¹⁵ For Collingwood, historical understanding consisted of “rethinking” the thoughts of historical agents. To understand why Caesar crossed the Rubicon or Napoleon invaded Russia requires us to “reenact” in our own minds the thinking that led to these actions. What did these historical actors think they were doing? This led Collingwood to the Hegelian conclusion that all history is the history of thought. He took strong exception to the attempt to introduce the study of psychological motives in history, as these, he believed, belonged to the province of the natural sciences and did not properly express human freedom and rationality.Footnote ¹⁶

Berlin's approach is similar but less intellectualist. History is not the story of thought alone, but of feelings, imagination, and perception. He prefers the term empathy or Einfühlung borrowed from the German philosopher J. G. Herder to show that history is a matter both of thinking and of feeling.Footnote ¹⁷Without the ability to enter imaginatively into the lives of different people inhabiting different ways of life, the observer may be a competent annalist or a reliable bibliographer, but can never acquire true historical insight. It is the ability to look at or imagine things from the inside that provides the key to Berlin's idea of historical judgment:

The idea that we can only understand the past—a monument, a text, an action—through an act of imaginative reconstruction runs into obvious difficulties. The first, alluded to in the passage above, concerns the limits of our imaginative capacities. How can we ever really know what it is to think or feel like someone else, especially if that someone comes from a distant time or culture? When I try to understand the world from another's point of view, it may be more likely that I end up attributing my understanding to them rather than theirs to me. When presidential candidate Bill Clinton told a supporter, “I feel your pain,” this was considered a powerful (although widely ridiculed) expression of empathy, but, if meant literally, it cannot possibly be true. We all know what grief is, but I cannot possibly feel your sorrow at the loss of a loved one, just as I cannot feel your joy at becoming an Olympic gold medalist. Between the subject and the object there will always be an unbridgeable empathy gap.

Let me take another, more extreme, example. In the third volume of her autobiography, The Force of Circumstance, Simone de Beauvoir tells the story of how she and a group of classmates were discussing the famous Hegelian philosopher Alexandre Kojève's theory of the unity of spirit. “But what if I have a pain in my foot,” Beauvoir objected. “We will have a pain in your foot,” her friend replied.Footnote ¹⁹ Whether this statement was meant literally (I think it was) or whether it was intended to show the extreme to which empathetic understanding can lead is left ambiguous in Beauvoir's text. The point is that taken to the extreme, empathy can lead to the obliteration of the distinction between self and other which is necessary for any possibility of critical judgment.

The second problem concerns how to test the capacity for empathic understanding. Berlin rightly understands that historical judgment is not simply a matter of accumulating facts and data sets but requires the abilities of the novelist and artist to discern meaning in the welter of events. The works of the greatest historians—Thucydides, Gibbon, Macaulay—have more in common with the best psychological novelists—Tolstoy, James, Proust—than they do with the great speculative philosophers—Plato, Spinoza, Hegel. But what standard can be used for evaluating two rival accounts of the same event? If judgment requires the capacity for critical evaluation, how do we choose between Gibbon's Decline and Fall and Mommsen's Roman History, or between Taine and Tocqueville on the French Revolution, or between Leo Strauss and Quentin Skinner on Machiavelli (although I have no difficulty with the latter)?

It is not just a question of who knows more about the subject—who has read more of the original materials, knows the context, or has canvassed a wider body of the secondary literature—but of who has a better insight into the subject. The question is, who is a better reader of the intentions of the principal actors, and this seems to rely upon a degree of imaginative reconstruction that cannot simply be reduced to the empirical techniques of data collection and research. Evaluation, then, becomes ultimately a matter of who has a better “feel” for the subject. The truth of a historical narrative, like the beauty of a painting or a piece of music, may only be revealed to the eye (or ear) of the beholder. It can only be shown, not demonstrated.

Berlin himself admits perplexity about how the capacity for empathetic insight is learned or acquired. Is it a gift we are born with like a talent for learning languages or for playing a musical instrument? Or is it an ability that can be honed and developed like any other skill? He refers to this capacity for empathy variously as a “gift,” a “talent,” and a “skill” requiring “depth of insight” and “knowledge of life,” but also admits that it is simply one of the many “imponderables” that form the basis of historical judgment:

Berlin is attentive to the humanist's ability to view others from the inside and ourselves from the outside. It is precisely this dual perspective that makes possible our capacity to render judgment. But perspectivism is itself an aesthetic creation pioneered in quattrocento Italy by Giovanni Alberti, who for the first time allowed the artist to depict the world from different points of view.Footnote ²¹ Nowhere was this perspectivism better expressed than by Alberti's contemporary, Niccolò Machiavelli, who in the Dedicatory Letter to The Prince describes himself as a painter who is able to achieve critical distance on his subject because he is able to view it from both above and below:

Berlin is correct to note that judgment requires the capacity for considering varying and even conflicting points of view, but it is not clear whether empathy actually enhances or impedes this capacity. In his book Against Empathy, the psychologist Paul Bloom argues that empathy is often a poor guide to decision making.Footnote ²³ Too often empathy is selective and biased and may end up confirming our prejudices rather than correcting them. It is easier to feel empathy for those around us or who are like us than those who seem distant or other. Similarly, empathy can lead us to make short-term bad decisions based on an immediate emotional response rather than working on long-term solutions. I may give five dollars to a homeless person because I feel moved by his plight, not considering that such an action may lead to continued drug dependency and a culture of panhandling. Bloom offers instead a case for “rational compassion,” suggesting that the right thing to do is a matter for reason and cool deliberation rather than sympathy and emotion.

The concept of judgment requires us to stand back from our immediate context or situation in order to gain some critical distance. In Critique and Crisis, Reinhart Koselleck pointed out that the Greek term for judgment—krisis—was originally a legal term meaning the ability to render a verdict, the weighing of pros and cons, in a court of law.Footnote ²⁴ Our ability to pass judgment requires that we put our feelings aside and consider the case from the standpoint of an impartial spectator. This does not mean adopting the classic “view from nowhere”—that is, some kind of ideal Archimedean point that views the world from a God's-eye perspective—but rather that we consider all the facts relevant to the case in order to do justice. The problem with empathy is that it requires us to “go native,” to view the past entirely through the lenses—the concepts of categories—of our historical subjects, which would in turn result in a withholding of judgment. Empathy would seem to enjoin not judgment but an endorsement of the practices and institutions that happen to exist at any one time. Judgment, as Nietzsche says in the epigraph to this paper, is an “uncomfortable mission” that requires not empathy but the powers of discernment and critical reason.

Judgment and political action

Judgment is a feature not only of historical understanding but also of political action. Judgment is required by the historian seeking to understand the past and also by the statesman deciding what to do in the present. These two activities—history and politics—are intimately linked in Berlin's mind. This does not mean that he thought of history as simply politics by other means but that each requires an ability to reflect, assess, and evaluate human actions in their complexity. If the historian seeks to make sense of the past, the statesman seeks to chart the future. Both require the ability to navigate the waters of uncertainty and contingency.

The argument for the importance of political judgment was lucidly developed in Berlin's essay “The Sense of Reality.” Berlin begins the essay with a discussion of historical determinism. “Everyone,” he avers, “no doubt believes that there are factors that are largely or wholly beyond conscious human control.”Footnote ²⁵The great shibboleth of modern historical systems builders—Comte, Hegel, Marx—is the belief that human affairs are subject to the same predictable laws and patterns as the natural world and that these laws are produced not by conscious human intentions but by certain deep structures of historical development. From the commonsense view that we are constrained in what we do by the circumstances in which we find ourselves, these thinkers jump to the conclusion that underlying the welter of human doings can be discovered something like a “key” to history that can explain all that we do in terms of one or a few variables, such as myth, or race, or class (gender was not part of Berlin's repertoire). The idea that we can interfere with these patterns and processes of development is seen as “illusory” by some and as “inevitable” by others, but in either case subject to the same invariant laws or forces.

Underlying these diverse systems of historical determinism is the belief that human beings must learn to adapt to the times and circumstances in which they find themselves. Our laws, philosophies, and moral values are all in their innermost essence held to be the products of their times. As Hegel famously put it in the Preface to the Philosophy of Right, “As far as the individual is concerned, each individual is in any case a child of his time … It is just as foolish to imagine that any philosophy can transcend its contemporary world as that an individual can overleap his own time or leap over Rhodes.”Footnote ²⁶ Those who attempt either to overstep their time or to return to an earlier one are doomed to failure, like Prince Ruprecht of Bavaria, who sought a restoration of the German monarchy. As the great literary critic Karl Marx once wrote, “Don Quixote long ago paid the penalty for wrongly imagining that knight errantry was compatible with all economic forms of society.”Footnote ²⁷

The problem with these deterministic theories of history is that they have been refuted by the very historical processes to which they appealed. The twentieth century was rife with examples of attempts to “force the end” as this term was used in eschatological thinking.Footnote ²⁸ The Leninist (and later Maoist) attempt to create communism by leaping over the stage of capitalist development or Hitler's attempt to create a pure Aryan community demonstrated just how much still depended on individual will in history. It seems hard to imagine that either the Russian Revolution or the Nazi seizure of power would have been possible without the outsized roles played by Lenin, Stalin, and Hitler. They all showed that individual initiative in history, however evil and distorted, cannot be safely ignored. They seem living refutation of the theory of historical inevitability. “Human beings and their institutions,” Berlin writes, “turned out to be much more malleable, far less resistant, the laws turned out to be far more elastic, than the earlier doctrinaires had taught us to believe.”Footnote ²⁹

The fact that these experiments in radical social engineering ultimately proved to be failures turned out to be not a detriment but rather an incentive to future revolutionaries. The very improbability of accomplishing events of such magnitude as the revolution became a perverse proof of its possibility. The failure to achieve “socialism in one country” or to advance the Thousand-Year Reich was not due to the impersonal forces of history but to failures of will and resoluteness. The appeal to the natural sciences became an inspiration for even more radical forms of social transformation. Lives and societies, it came to be thought, can be altered in much that way that modern experimental sciences have split the atom or altered our genomic structure. The lesson drawn was that history is more subject to continual human control and manipulation than was previously believed. A determinist theory of history thus gave rise to a new spirit of radical voluntarism where everything is made to depend on human volition and the will to power. As the Italian Marxist Antonio Gramsci said with a Nietzschean turn of phrase, “Pessimism of the intellect, optimism of the will,” or as the great Zionist leader Theodor Herzl wrote, “If you will it, it is no dream.”Footnote ³⁰

Berlin attempted to chart a third way different from determinism and voluntarism. What distinguishes the statesman from the theorist or doctrinaire consists in possessing “the sense of reality.” By this term he means something like the capacity for historical empathy developed in his historiographical writings. The sense of reality is a feeling that

The sense of reality consists in the skill of knowing what will work and what will not, what can be done and what cannot, and what fits and what does not. To this kind of knowledge, Berlin asserts, “there is no key.”Footnote ³²

Here as elsewhere there is something about Berlin's idea of the sense of reality that defies rational reconstruction. His description of it as a “sense” suggests its somewhat indeterminate character and resistance to theorizing. He refers to this sense as “the kind of semi-instinctive integration of the unaccountable infinitesimals of which individual social life is composed” and compares it to a musical sense, possessing “an element of improvisation, of playing by ear, of being able to size up the situation, of knowing when to leap and when to remain still, for which no formulae, no nostrums, no general recipes, no skill in identifying specific situationsas instances of general laws can be a substitute.”Footnote ³³

Berlin is clearly aware that his conception of the sense of reality borders on a kind of irrationalism, the same charge brought against Michael Oakeshott's idea of following a tradition of behavior.Footnote ³⁴ The question that dogged Oakeshott is that if following a tradition consists in “the pursuit of intimations,” how do we know which intimations to follow? Oakeshott refused to provide a road map in part because he regarded a tradition as being like a “conversation” consisting of many voices. His goal was not to select one voice above all others, but simply to keep the conversation alive. The principle to be pursued is continuity with the past where this means acting in such a way that the various parts of a tradition fit together or cohere like the pieces of a jigsaw puzzle.Footnote ³⁵

In a lengthy footnote Berlin tries to address this problem by distinguishing his understanding of the sense of reality from Gilbert Ryle's distinction between knowing how and knowing that.Footnote ³⁶ The former consists in the possession of a skill or an art like making an omelet or painting a portrait; the latter consists in the ability to give an account or explanation of the activity. I may know that if I turn on the light switch on my wall the light will come on but could give no theoretical explanation of why that is the case. Ryle's distinction between knowing how and knowing that—like Oakeshott's similar distinction between practical and technical knowledge—assumes that a living practice is always more vital and complex than any theory could possibly be. Contrary to both Ryle and Oakeshott, Berlin wants to show that the sense of reality is not entirely distinct from reason-giving explanations.

Berlin illustrates the sense of reality by reference to the Greek classicist Richard Porson, whose discoveries—now referred to as Porson's law—describe the metrical pattern of Greek iambic trimeter. Porson would not have been able to carry out his philological work without “an ability to co-ordinate an untold number of dimly articulated data—and then to take the crucial step, or undergo the crucial experience—to discriminate and articulate to himself a pattern which provided all or many of the desiderata.”Footnote ³⁷ Perhaps Porson's discoveries are only a soi-disant law. Berlin speculates about whether these discoveries could have been achieved by a computer that had been programmed with all the relevant data, but concludes that no amount of algorithmic reasoning can replace the inspired guesswork of a philological genius. This is not to say that Porson's abilities represent some kind of mystical intuition, but Berlin admits that it would be difficult to generalize Porson's discoveries in part because “the facts are too minute, there are too many of them, [and] too few persons are adept at such pearl-diving operations.”Footnote ³⁸

The situation faced by an editor of an ancient text is not unlike that of the statesman faced with a critical situation who needs to choose between various courses of action. In both cases the knowledge of what to do will be based on the capacity for generalization on the one hand—how does the current situation or text fit in with or resemble others of its kind?—and the “scrupulous minute fitting of fragments into a pattern” on the other. It is the ability to move between the general and the particular—what Berlin refers to metaphorically as the upper and lower levels of experience—that describes the sense of reality.

Judgment and education

Berlin's effort to find a via media between determinism and voluntarism was further explored in his short essay “Political Judgment.”Footnote ³⁹ He begins this essay by asking, what is it to have good judgment in politics? If judgment is a kind of knowledge, what kind is it and how can this judgment be acquired and assessed? Is political judgment a science that can be formulated in laws and rules or an art that defies generalization?

Berlin addresses the question by reformulating some familiar positions. The idea of a science of politics goes back to ancient times, but it was in the seventeenth and eighteenth centuries under the influence of the scientific revolution that this aspiration achieved its greatest expression. The goal of the great early modern philosophers was to create a moral and political physics that could aspire to the certainty of mathematical physics. Attempting to consider the moral and political universe as so many “lines, planes, and solids” (to use Spinoza's image), it was thought possible to put knowledge on a new, more secure foundation.

Under the influence of Newtonian mechanics, philosophers of the Enlightenment conceived of society along the lines of a perfect self-regulating machine that would be impervious to “intestine disorder,” to use Hobbes's famous metaphor. It is often believed that the American founders operated under this belief in their attempt to create a system of checks and balances that would establish a perfect equilibrium between the different branches of government and the diverse interests of society. “Enlightened statesmen will not always be at the helm,” James Madison warned in Federalist #10, suggesting a system that would prove resistant to human folly and error.Footnote ⁴⁰ The image of the Constitution as “a machine that would go of itself” was a metaphor used to describe a political system that could operate by its own laws and processes without the need for creative statecraft.Footnote ⁴¹

In the period following the French Revolution, the mechanistic model of the Enlightenment was rejected in favor of a more organic analogy derived from the biological sciences that regarded society not as a machine but as a living organism subject to the cycle of birth, growth, and decay. On this account, societies cannot be reconfigured along the lines of a rational plan or design, but are the products of deep economic, cultural, and linguistic forces that shape their distinct national characters. Montesquieu, an early proponent of this view, argued that each society is governed by its unique national esprit that gives shape to its customs and laws.Footnote ⁴² German thinkers like Fichte and Hegel conceived each people as constituted by a Volksgeist that is the source of communal norms and purposes. Individuals are not “rational actors” but are shaped by the irrational forces of habit, tradition, myth, and prejudice. Out of this intellectual matrix developed the new discipline of sociology.Footnote ⁴³

In the American context, this view reached its apogee in the Progressive Era and the presidency of Woodrow Wilson. Wilson was the first US president not only to have a Ph.D., but also to have been the president of the American Political Science Association. In Constitutional Government in the United States, he argued that the older static model of the Constitution, with its system of checks and balances, needed to be replaced by an updated evolutionary conception based on beliefs about mutability and adaptation. “Living political constitutions,” he wrote, “must be Darwinian in structure and practice.”Footnote ⁴⁴The doctrine of the “living constitution” regarded the Constitution not as a static, timeless document but as one that should be constantly reinterpreted in light of the changing needs of society.

For Berlin, political judgment can neither be deduced from the timeless laws of nature nor derived from the changing detritus of history. Political judgment is a skill like any other and does not need the help of a general theory of history or nature to sustain it. “What makes statesmen, like drivers of cars, successful is that they do not think in general terms … Their merit is that they grasp the unique combination of characteristics that constitute this particular situation—this and no other.”Footnote ⁴⁵ Berlin speaks of the possessors of this political skill in artistic terms as people graced with “exceptional sensitiveness” to their surroundings and with “antennae” that allow them to hold together “the specific contours and texture of a particular political or social situation”:

Berlin even adds a Nabokovian touch—after his great countryman—to this description of the statesman as being like a skilled lepidopterist. “The gift we mean entails,” he writes, “above all, a capacity for integrating a vast amalgam of constantly changing, multicolored, evanescent, perpetually overlapping data, too many, too swift, too intermingled to be caught and pinned down and labeledlike so many individual butterflies.”Footnote ⁴⁷

Berlin is especially interested in what distinguishes successful statesmen from philosophical geniuses and why, by implication, the latter often appear politically foolish. They are to some degree blinded by their own genius. Einstein may have been a brilliant theoretical physicist but his political reflections on world peace seem almost touchingly naive. Russell was a brilliant logician but his writings on marriage, religion, and international relations show little appreciation for the complexities of political reality. What is it, then, that statesmen possess that others do not? “What are we to call this kind of capacity?” Berlin asks:

Finally, good judgment in any area of life consists in the ability to “improvise.” Like a musician creating unfamiliar riffs on a jazz standard, having judgment consists in the skill of working within an established idiom but expanding upon and developing the possibilities latent within it. It is the same skill possessed by the master chef who is able to create new combinations of tastes from a familiar palette of choices. Judgment is not the mechanical application of a rule or fixed standard to changing circumstances, something like the demand for strict consistency, but the ability to creatively adapt rules to new and unforeseen situations and master them. Berlin does not neglect the role that luck—what Machiavelli called fortuna—plays in politics and wonders why it is that people with good judgment seem to display better luck than others.

Can judgment be taught?

To return, then, to our beginning: Berlin regards judgment as a synthesis of both rational or deliberative and aesthetic criteria, yet these are neither sufficiently distinguished nor defined. Is good judgment as an art or skill that can be learned and taught or is it more a matter of what Bernard Williams calls “moral luck,” something we happen to possess almost as a gift of nature or grace?Footnote ⁴⁹

The classic case for judgment as a cognitive virtue was given by Aristotle. He was the first philosopher to attempt to theorize judgment as a form of practical rationality. Like all the virtues, Aristotle believed, judgment was a form of knowledge. It cannot necessarily be set out in terms of formal rules and syllogisms, but it is an activity for which reason-giving is appropriate. Judgment is associated by Aristotle with deliberation over means rather than ends. No doctor, he tells us in the Ethics, deliberates over health and no general deliberates over victory. They deliberate over the means to achieve health and victory. Deliberation occurs when the means are in doubt and where opinions differ over what to do.

Judgment concerns discretionary behavior where there is choice and deliberation between various courses of action.Footnote ⁵⁰ It can, therefore, be distinguished from two other forms of decision making. One is that judgment is like opinions of taste where reasons seem superfluous. This may be summarized in formulae like “beauty is in the eye of the beholder” or chacun à son goût. These are preferences that appeal to me for no other reason than that I happen to like them. Discretionary judgments, by contrast, are those for which reasons can be given. But discretionary actions cannot be reduced to rules and syllogisms. Stopping at a red light does not require discretion on the driver's part. It is simply a part of the rules of the driving code in the same way that running the base paths is a part of the rules of baseball. Following the rules of the road, like knowing the shortest distance between two points, is not so much an example of discretionary behavior but simply of knowing how to read a map.

Discretionary acts always concern matters that could have been otherwise, where there is some room for choice and, therefore, error. A statesman's decision to go to war or to raise or lower taxes falls under this category. No one could say that these are simply whims or personal preferences and yet they are not actions for which precise rules can be invoked either. Berlin tells the story that he admits may be apocryphal that when the prime minister, Lord Salisbury, was asked on what principle he had decided to go to war he replied, the same principle that he decided on whether to carry an umbrella: he looked at the sky.Footnote ⁵¹ There is, in short, no rule that tells someone when is the right time to go to war. The answer, as Wittgenstein might have said, is “look and see.” These are matters of practical judgment over which reasonable people may and do disagree. In fact, disagreement or the possibility of disagreement is built into the very concept of judgment. But the fact that we disagree indicates that we disagree over something. We do not generally argue over someone's tastes in music or clothes—these tend to be things of which we approve or disapprove but cannot be called right or wrong—but we can and do argue over whether a judgment to declare war or raise taxes is or is not the right thing to do. There is an ineradicable element of moral rationality built into our conception of discretionary behavior.

Berlin sometimes seems to think of judgment along these Aristotelian–Wittgensteinian lines as a deliberative activity that can be imparted, if not through rules then at least through examples. His character sketches of great political leaders—he called them éloges after the French tradition of funeral oratory—were clearly intended as a form of exemplary history that can expand on our conceptions of the range of human possibilities.Footnote ⁵² His examples often mimic his famous hedgehog-and-fox distinction applied to the realm of politics. Sometimes he praises the ability of a Churchill to dominate and lead his country in a time of national crisis through his almost single-minded vision; at other times he praises the small-bore skills of a leader like Chaim Weizmann who knew how to operate behind the scenes in the corridors of power. Berlin's use of exemplary figures indicates that there is no one way of exercising good judgment, but that it depends on personality, context, and circumstance.

Berlin admits that judgment in politics is not a moral quality but something that can be possessed by the virtuous and the vicious alike. It is a quality possessed by all “successful statesmen.” As models of successful leaders, he cites Talleyrand, Lincoln, Disraeli, Atatürk, and Franklin Roosevelt, while his list of fanatical and visionary leaders includes Robespierre, Napoleon, Lenin, Hitler, and Stalin.Footnote ⁵³ But what distinguishes the two lists since both clearly achieved some kind of success? If judgment is a prerequisite for political success, what determines success? Without a better definition of what defines success, Berlin's own judgments often seem like a list of personal likes and dislikes.

The relation of judgment to success is often very difficult to determine in part because timing is essential. “To adapt to the times” was Machiavelli's formula for successful statecraft. The ability to gauge the times is crucial for successful action but success often remains an elusive category. How do we know when a person has been successful (or not)? A person may be successful in the short term but a failure in the long and vice versa. Was Hitler unsuccessful because the Thousand-Year Reich lasted only twelve years? Jesus might have been considered a failure in his own time—he was a classic “unarmed prophet”—but his spiritual propaganda later conquered the Roman Empire. In their book Legacies of Losing in American Politics, Jeffrey Tulis and Nicole Mellow argue that electoral defeat in politics, as in the cases of the Anti-Federalists or Barry Goldwater, led to the successful resurgence of their causes later on.Footnote ⁵⁴ Churchill once apparently—I have no idea whether he really did—said that success is the ability to go from failure to failure with no loss of enthusiasm. This is witty but cannot be true. A person who met with repeated failure, however enthusiastic, could not possibly be said to have good judgment even if such a person meets with occasional success. As the saying goes, a stopped clock is still right twice a day.

Success provides no clear standard for determining judgment. Consider the following scenario. A baseball game is in the bottom of the ninth inning. The visiting team is holding on to a one-run lead with runners on base. The manager considers whether to remove the starting pitcher. He checks the statistics about the number of pitches thrown and calls a meeting on the mound. He consults the pitcher on the state of his arm, he asks the catcher his evaluation of the quality of the pitches, and, of course, he relies on his experience of the game based on similar situations he has encountered. On the basis of what he learns, he brings in a relief pitcher who promptly surrenders a game-ending home run. Did the manager use bad judgment? No. On the basis of everything he has learned, he did what he thought was the right thing, but there is no algorithm that can account for every contingency and happenstance. Or consider a poker player with three aces. He bets his stake only to find that his opponent has a straight. Was he wrong to do so? No, again. The odds favored his bet but sometimes even the odds are misleading. Good judgment does not always guarantee successful outcomes. Sometimes the best plan may be to have a little luck.

At times Berlin equates judgment with the ability to know how to act and when, with knowing the right or the appropriate thing to do; however, as we have seen, it not just a matter of habits and experience, but is associated with aesthetic faculties like intuition, insight, and imagination. The relation of judgment to the moral imagination is a largely modern trope, developed notably by Burke, Hume, and Kant, who considered the imagination not the source of error and confusion, but of our uniquely human capacity for critical self-reflection. It is often associated with the romantic cult of self-creation, someone who relies only on himself and his own resources, or who, in Kant's memorable phrase, “gives the rule to art.”Footnote ⁵⁵ At the core of this conception of self-creation is the idea that our judgments cannot be measured by the standards of truth or falsity, right or wrong, good or evil, but are the expressions or, as might be said later, the “values” of what we are or what we aspire to be. The subjective element of judgment—that it is mine and mine alone—takes priority over any specific content or direction.

Berlin often regards judgment in explicitly Herderian terms as a form of self-expression.Footnote ⁵⁶It is not a type of knowledge but an exfoliation of individual personality. This is what, he believes, distinguishes the natural from the human sciences. A scientific experiment can presumably be repeated by anyone; it makes no difference in principle who is its author. In fact, the impersonality of the procedure must be guaranteed if the accuracy of the results is to be protected. But a work of history, music, art, or philosophy bears the unmistakable imprint of its creator. We like to think that a Mozart concerto, a Cole Porter lyric, or a Frank Stella painting could not have been produced by anyone else. Each carries the unique stamp of its creator. Berlin speaks of judgment less as an intellectual capacity than as an aesthetic faculty, comparing it to the ability to create and improvise that is the gift of artistic geniuses. It is a unique expression of individual creativity.

Good judgment, like good taste, is ultimately a form of je ne sais quoi. Like Porson's ability to detect corruptions in earlier editions of Greek tragedies, judgment is not a matter of having more information or knowing more facts, but the ability to make connections and discern patterns that no one else has seen, to explore possibilities that no one else has entered. To detect grammatical minutiae in a text is not a skill that can be taught—although it no doubt requires a great deal of philological training—but is a rare “perceptual gift” like discerning the pattern in a carpet behind the welter of colors and shapes. This remains an unearned gift like an ear for music or a talent for drawing. How we acquire these gifts remains a mystery that no amount of experience can provide.

The question that Berlin's work asks us to consider is whether our imaginative faculties and sympathies can ever really be educated, much less passed on to others. Is an education of the sentiments really possible? I am reminded of a scene from Otto Preminger's great film noir classic Laura. Here a police detective, Mark McPherson, played by Dana Andrews, is interrogating a murder suspect, Waldo Lydecker, a self-absorbed radio personality played by Clifton Webb, who admits that his love for Laura set him on a program of attempted moral reform:

Admittedly, Lydecker may be an unpromising case study for moral self-reflection, but the lesson seems to point to the limits of our capacity for empathetic education.

There is much in Berlin's writings to suggest he doubts whether judgment can be taught. Historical and political judgment, he believes, is shaped by our capacities for insight and empathy; that is, the ability to imaginatively see the world from another's point of view and even to feel what they feel. Yet this capacity for empathetic understanding remains elusive even on Berlin's account. How, exactly, is empathy acquired? Do some people just seem to possess this enlarged capacity for moral outreach? Our imaginative capacities seem more like an undefinable gift of nature than of instruction or training. Why does one person have a talent for the violin while another is tone-deaf? Why does one person have the knack for moneymaking while another follows one dead end after another? Our imaginative and creative capacities are randomly distributed and have little to do with our merit or desert, but are to a large degree the product of luck or chance. “Man's ‘creative’ abilities, which are more admirable than any of his products, are not themselves produced by man,” Leo Strauss once wrote. “The genius of Shakespeare was not the work of Shakespeare.”Footnote ⁵⁸

In the end, good judgment requires a combination of both the cognitive and the affective dimensions of the mind. Aristotle was right that judgment is a form of practical rationality that can be perfected through practice and experience. But Berlin added a crucial dimension of imagination and the aesthetic disposition that is the product of what he called the “romantic revolution.” He may not have adequately distinguished between that rational and the nonrational components that make up decision making, but he was right—incontestably right—to draw attention to both these factors.