West Point's recently released list of the top 10 military classics is replete with doorstop-sized accounts of conflict from ancient to relatively modern times -- but almost completely neglects insurgency, terrorism, and other forms of irregular warfare. The U.S. Military Academy's list does a fine job of capturing the "horizontal" dynamic of clashes of roughly equal great powers armed with the most advanced weapons. But the history and shape of the world system have been just as influenced by the "vertical" axis -- the unequal struggles that have seen guerrillas, bandits, and commandos waging "wars of the knife" against empires and nations. And it is this latter mode of conflict that has dominated world affairs for the past half-century -- and will likely do so for at least a century to come.
With this in mind, let me supplement the West Point list. For those drawn to West Point's recommendation to read Thucydides, I suggest taking a look also at Sallust's The Jugurthine War. Jugurtha of Numidia (today's northern Algeria) fought a bitter guerrilla war against Rome, some 50 years before Julius Caesar's great campaigns, that Sallust captured with verve. He also spoke to the corruption of Roman character that came with protracted exposure to this kind of fighting.
Hans Delbrück, whose four-volume history of ancient, medieval, and early modern warfare that West Point selected, can be nicely complemented by Lt. Gen. John Bagot Glubb's The Great Arab Conquests. His survey of the sweeping seventh-century victories of Muslim warriors is of the highest analytic and literary quality, a principal observation being that much of the world of that time was shaped by the irregular "pirate strategy" the Arabs adopted. That is, they used the desert as an ocean and came raiding from it, again and again, with startling success.
The West Point list also focuses on several important philosophers of war: the aphoristic Sun Tzu; the turgid, elusive treatises of Machiavelli and Clausewitz; and Jomini's geometrically inspired principles. Jomini in particular, with his emphasis on angles of approach and other seemingly precise formulas, captured the minds of generations of military leaders. His ideas about how to properly mass one's forces and take the offensive remain powerfully prominent in -- if not especially useful to -- current U.S. strategic thought. Irregular philosophers of war are, by comparison, few. Mao Zedong is certainly the best, though his On Guerrilla Warfare is very nearly as vague as Sun Tzu. Yet Mao's key insight for irregulars -- centralize strategy, decentralize operations -- is still the polestar.
For a more operationally oriented study of land battles, West Point chose Ardant du Picq's Battle Studies. This is a curious choice. Col. du Picq was killed in the Franco-Prussian War, but his belief that good morale could overcome concentrated firepower animated French strategic thought up to and during World War I -- with near-catastrophic results. For the period in question, I suggest two alternatives. First, there is Col. Charles Callwell's survey of the many modes of irregular warfare, Small Wars -- find the third edition, the one with the insightful introduction by eminent military historian Douglas Porch. The second book is by John Reed -- also the author of Ten Days That Shook the World about the Russian Revolution -- whose account of Pancho Villa in Insurgent Mexico is one of the finest eyewitness accounts of an insurgent campaign ever written, even taking into account T.E. Lawrence's Seven Pillars of Wisdom.