On Grand Strategy by John Lewis Gaddis: 2 Tenets for Future Leaders

On the anniversary of the publication of John Lewis Gaddis’ On Grand Strategy, this is a book review that summarises some learnings from both On Grand Strategy and the classical texts that inspired it.

Most of us think of Tolstoy and F. Scott Fitzgerald as among the greatest authors in literature. But John Lewis Gaddis draws strategy lessons from both writers in his most recent book, On Grand Strategy, which grew out of his grand strategy seminars at Yale and the U.S. Naval War College. Published almost a year ago, On Grand Strategy is fun to read, full of exciting stories and wit, and can be condensed into important principles that all leaders should pay heed to. Written in great prose with simple yet crucial lessons rooted in the stories of men (and a woman), On Grand Strategy will be a modern classic on many future leaders’ bookshelf.


Two Central, Tethered Principles

Should On Grand Strategy be summarized in one sentence, it would tether two simple tenets: great leaders must be both a hedgehog and a fox, comfortable in juggling combinations, contradictions, and contrasts; remember that your aspiration is limitless but your capabilities are constrained, so balance your ends and means.

Be Both a Fox and a Hedgehog

A hedgehog and a fox (Credit: Kacee @kc_6201)

A hedgehog and a fox (Credit: Kacee @kc_6201)

Isaiah Berlin, a Latvian-born British philosopher, describes two categories of leaders in Aesopian term: “The fox knows many things, but the hedgehog knows one big thing.” A hedgehog relates everything to a central vision but a fox pursues many unrelated or contradictory ends. Political psychologist Philip E. Tetlock’s 15-year studies showed that foxes do better at predicting the future of world politics. But too fox-like also paralyzes a leader from uncertainties, who must appear to know what they do even when they don’t.

So the book opens with the Persian King Xerxes’s hedgehog vision to invade Greece and his fox-like uncle Artabanus’ hesitation to follow suit. The former suffered a humiliating defeat at the hands of Greeks, his defeat forever sealed in Herodotus’ The Histories, the latter forgotten quickly by the world of history. The poignant lesson from Xerxes lies in the fact that both he and his uncle failed F. Scott Fitzgerald’s test of first-rate intelligence, that of “the ability to hold two opposed ideas in the mind at the same time, and still retain the ability to function.” The book is filled with such polar exemplars: the old Pericles, Julius Caesar, Augustine, Philip II, George III, Napoleon, Wilson, all hedgehogs trying to herd foxes; the younger Pericles, Augusutus, Machiavelli, Elizabeth I, Founding Fathers, Lincoln, Franklin D. Roosevelt, all foxes with compasses.

Leaders should to be both a fox and a hedgehog. Go with the flow, “[h]aving determined your destination, you set sails, motivate rowers, adjust for winds and currents, avoid shoals and rocks, allow for surprises, and expend finite energy efficiently.” For, quoting Spielberg’s film Lincoln, “[i]f in pursuit of your destination, you…achieve nothing more than to sink in a swamp…what’s the use of knowing true north?” Woodrow Wilson, the builder with a grand vision, disappointed his generation in the aftermath of WWI, but Roosevelt, the “juggler”, surpassed his generation’s expectation. Roosevelt once said: “I may be entirely inconsistent if it will help win the war.” Perhaps Roosevelt has “a second-class intellect” but he definitely passed Fitzgerald’s test for first-rate intelligence.

Align Means with Ends

Napoleon retreating from Moscow (Credit: Adolph Northern)

Napoleon retreating from Moscow (Credit: Adolph Northern)

Gaddis also reminds leaders to match their aspirations with capabilities through time and space, adjusted for scale. Both Clausewitz and Tolstoy, two of Gaddis’ favorite authors in the book, understand that “ends, potentially infinite, can never be means, which are poignantly finite.” To go to Mars, you need to have long-distance rockets. To build a billion-dollar smartphone app, phones and wifi must be widely adopted. Sounds simple, pretty much like common sense?

Unfortunately, Gaddis observes that common sense is like oxygen, the higher leaders climb, the less common sense they get. “Everything in war is very simple, but the simplest thing is difficult,” otherwise how could we explain the recurring military miscalculations overstretched by ambitious leaders? Xerxes’ grand army crossing into Greece, the Athenians sailed to fight in Sicily, the Romans marched into the Teutoburg forest, the Spanish Armada destroyed in the English Channel, the British struggle in the American revolution, and Napoleon on the river Niemen to Russia. We’d ask what were they thinking? What had they forgotten? But history is easier read than made.

Clausewitz would suggest that they all failed to perceive “truth at every point,” which in these military instances meant climates, landscapes, logistics, their troops’ morale, and the enemies’ strategies. To see truth at every point, the leader requires the ability to live among contradictions through what Machiavelli calls “sketching,” assessing the “knowns”, such as geography, climate, your own capabilities, the “probabilities”, as in the goals of adversaries, the reliability of allies, and your country’s capability to endure adversity, and finally the “unknowns”, which lurk in the intersections of the first two. And so Napoleon lost his war by confusing aspirations with capabilities while Lincoln, a true master of common sense, preserved his Union by balancing ends with means.

Wisdom Rooted in Literature

That this book on a life-and-death subject is entertaining to read lies partially in the absence of dense modern political science and international relations theories, something that Gaddis addresses early on.

Historians…tend to avoid the generalizations upon which theories depend…Theorists, keen to be seen as social “scientists,” seek “reproducibility” in results: that replaces complexity with simplicity in the pursuit of predictability. Both communities neglect relationships between the general and the particular — between universal and local knowledge — that nurture strategic thinking.

Closing this gap between history and theory, Gaddis offers “an older way” proposed by Machiavelli: learning from “the actions of great men, learned…from long experience with modern things and a continuous reading of ancient ones.” Therefore, On Grand Strategy relies heavily on classical texts, such as Thucydides’ History of the Peloponnesian War, Machiavelli’s The Prince, and Clausewitz’s On War, and draws case studies across over two millennials, from Xerxes and Pericles all the way to Lincoln and FDR.

A statue of Machiavelli (Credit: Hulton Archive/Getty Images)

A statue of Machiavelli (Credit: Hulton Archive/Getty Images)

Presenting an eclectic verdicts on statesmen, monarchs, and writers, Gaddis leverages not just references to other historians’ works but also from his literary knowledge in literature. Given the complexity of reality, Gaddis argues that only narratives, the reconstitution of the past as histories, biographies, poems, plays, novels, and films, or what he calls dramatization, can emancipate reality from a scholar’s enslavement to theory and archive to fully illustrate dilemmas and choices across time.

Because of this, Gaddis quotes fictional works generously. Tolstoy’s War and Peace is repeatedly featured in quotation blocks. Other literary “flirtations” include Jane Austen, Virginia Woolf, Hermann Broch, F. Scott Fitzgerald, John Williams, and Milan Kundera. This does not mean Gaddis is old-fashioned. He borrows from modern social science when the necessity arises, such as quoting Daniel Kahneman’s Thinking Fast and Slow.

Training Leaders via Classics

(Credit: Michael Liccione)

(Credit: Michael Liccione)

In the age of big data and machine learning, Gaddis’ “partiality” of historical literature and drama over social sciences, contemporary case studies, and technology jargons might seem outdated. An anecdote from Gaddis in classroom could shed some light on his conscious choice of classics over contemporary methods: at Yale, Gaddis once asked his students, all of whom had to read War and Peace page by page for his grand strategy seminar, what connections Prince Andrei, Natasha, and Pierre, characters in War and Peace, could have to their very different lives? After a long pause, three students simultaneously said: “They make us feel less lonely.”

For without some sense of the past the future can be only loneliness: amnesia is a solitary affliction. But to know the past only in static terms — as moments frozen in time and space — would be almost as disabling, because we’re the progeny of progressions across time and space that shift from small scales to big ones and back again. We know these through narratives, whether historical or fictional or a combination of both.

Hence, this book aims to train a new generation of leaders not through high-tech wizardry, theoretical frameworks, or particular ideologies. There are no 3-step formulae or life hacks promising you 10x success rate. Instead, it offers the kind of training that Clausewitz prefers: drawing on principles extending across time and space, a.k.a. history, so a leader intuitively senses what has worked before or not and then re-apply the principles to the situation at hand to form a plan for achieving a future goal.

That being said, Gaddis is not a nihilist on theoretical frameworks. He takes the attitude of Clausewitz toward theory: he “places theory within the category of rules to which there can be exceptions, not laws that allow none.” Gaddis argues that theory should serve practice and practice should correct theory. Theory is for training leaders but not a navigational chart for the unforeseen.

Room for Improvement?

No book is ever perfect. Some reviews, such as by John Nagl on WSJ, argues that On Grand Strategy lacks writings on Eastern traditions and gives only a brief moment for Sun Tzu. Personally, I speculate that Gaddis is simply taking his own principles by heart, for while a writer can have a grand ambition, a 300-page book can only host so many tales. Limited by his education and training, it is reasonable that he focuses on the history, literature and philosophy over 2,500 years of Western civilization.

Such “imperfection” is good news for other ambitious strategists with deep knowledge of the other half of the hemisphere. I can only look forward to another author in the near future, perhaps Oriental, who would build on top of On Grand Strategy by engaging in the wisdom from Asia.


In a time when bestselling authors are selling buzzwords, tech jargons, and formulas on success, Gaddis grounds future leaders to the past. Not only does Gaddis offer readers a thoroughly engaging and entertaining journey through western history, but he also reveals the value of liberal arts education, combining history, literature, and philosophy, for leaders and statesmen. With an understanding of fox and hedgehog and the need to match ends and means, one starts to look at contemporary events, such as the Brexit and the Green New Deal, through new angles. That’s perhaps one of the best gifts Gaddis gives to us: a new generation of leaders who can extract common sense through complexity and make wise decisions.

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