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Key point: These men were products of the times they lived in, but their words remain relevant today.
Ranking military strategists against one another is a slippery chore. Apart from the obvious differences among strategists—the historical epochs when they lived, the state of martial technology in their lifetimes, warmaking methods then in vogue—there's a more basic difference. Some strategists are mainly practitioners; others are mainly theorists.
So how do you judge, say, a field soldier like General Ulysses S. Grant—a victor whose bulldog approach to battlefield combat is Carl von Clausewitz's "principle of continuity” made manifest—against a Clausewitz, an indifferent soldier whose accomplishments as a man of letters shape strategic thought and actions to this day? Hard to say.
Oddly, many of the greats seem to be indifferent practitioners who started scribbling down their insights after being defeated, cashiered or both. Maybe failure clears the mind. It hardly renders their ideas moot. Indeed, you ultimately have to favor such teachers over doers. They mine the historical record—the record of the deeds of great captains—for insight into the arcane art of strategy. Napoleon and Frederick the Great are fixtures in Clausewitz's On War. Lord Horatio Nelson is the face of Alfred Thayer Mahan's sea-power theories. Thucydides has Pericles, Alcibiades, Brasidas, Lysander and many others. Practitioners supply the data for teachers to analyze and pass on.
You need both doers and thinkers to perpetuate strategic thought—but ultimately, the thinker with a feel for battlefield realities trumps the practitioner with little flair for analyzing his experiences, drawing out the takeaways and recording the results. Hence, wordsmiths, not commanders, dominate my list of “History's Five Greatest Military Strategists.” A ranking of self-made strategists might encompass warrior-statesmen from Julius Caesar to Nathanael Greene to Abraham Lincoln. With that disclaimer, onward!