ith The Road Not Taken, Max Boot has written not one book but three: a biography of Major General Edward Lansdale, the near-mythic covert operator of the 1950s and 1960s; a plea for an approach to counterinsurgency warfare that is now, after Iraq, out of fashion; and a picture of the post–World War II American plunge into Asia. Boot, a Commentary contributor and scholar at the Council on Foreign Relations, has bundled these volumes together in a massive, grippingly written narrative. He has delved into the archives, talked to living participants in his hero’s life, and walked the crowded streets and hamlets, the mountains and rice paddies where it took place. The Road Not Taken is a marvelous as well as an important read.

Unlike many of the early spooks of the wartime Office of Strategic Services (some insisted that OSS stood for “Oh So Social”) and early postwar Central Intelligence Agency, Lansdale was no blue blood. The son of peripatetic parents, he was born in Detroit in 1908 and flitted across the country, finally completing most of a college degree at UCLA. He got his start in advertising. If World War II had not occurred, he probably would have stayed in it.

But in his early thirties, the war swept him in as it did so many young men. He served in OSS and later in the U.S. Army, always in military-intelligence assignments at home, where he showed exceptional skill in developing rapport as an interrogator and general fixer (coaxing Sumatran crew members on a Dutch-flagged ship to stop a strike in 1942, for example). When the war ended, he was shipped out to the Philippines to serve as an intelligence officer there, helping the Philippine service recover from Japanese occupation and coping with Japanese prisoners of war being shipped back home. After three years (during which he picked up a mistress whom he eventually married almost 30 years later), Lansdale returned home—only to come back in 1950 when he became the closest aide to Ramon Magsaysay, the Philippine secretary of national defense. From there, Lansdale twice served in Vietnam: once from 1953 to 1957, and again from 1965 to 1968. In between, and despite his own misgivings, he helped mastermind Operation Mongoose, the CIA’s shambolic and abortive effort to overthrow Fidel Castro.

He ended up as a major general in the United States Air Force but had nothing to do with airplanes save flying in them as a passenger. What he did do was unclassifiable. He designed rehabilitation programs for Philippine guerrillas coming in from the countryside, and engineered Ngo Dinh Diem’s successful campaign to beat down the sectarian and criminal armies in South Vietnam that in the mid-1950s posed as great a threat to that country as the Communist insurgency did. He had harebrained ideas and good ones; he was a clear and copious writer, but his greatest skill was his ability to form enduring human connections. This man who struggled with foreign languages—he spoke neither Tagalog nor Vietnamese, and even French was beyond him—had a rare gift for getting inside Asian societies of which he had known nothing, and establishing relationships of trust that went beyond friendship.

The story of the man himself is fascinating—how he juggled an unhappy marriage and a fiery mistress, his battles with the bureaucracies of the military and the Department of State, his commitment to basic elements of freedom and democracy while participating in dirty tricks some of which came perilously close to what we would now consider war crimes. Unlike some colorful figures, he was a hard and conscientious worker, dedicating himself to exploring the Philippine or Vietnam villages, or drafting 32-point plans, or patiently studying the folklore, from music to soothsaying, of the countries in which he found himself.

Had it not been for the mobilization and upheaval of the time, a Lansdale could not have made it into four organizations—the OSS, the CIA, the Army, and the Air Force. He could not have gotten away with engineering the dismissal of ambassadors, being the confidential adviser of the leading Filipino politician, and securing promotion after promotion without commanding much of anything. Nor could his unique talents have found quite the purchase they did. There were opportunities to be found in the crises into which Lansdale plunged: the disruption of the Japanese occupation of the Philippines and Vietnam; the emergence of new, nationalistic governments in the wake of the voluntary dismantling of American colonial rule; the more grudging retreat of the French in Indochina (who, if Boot is correct, were sufficiently angry at Lansdale to try to assassinate him). These were countries at once remote and opening up to the world, rurally centered yet urbanizing, traditional, and being transformed.

The story here is that of Lansdale’s life and times, and one can read The Road Not Taken solely for the purpose of understanding both. Boot adds a third theme, however, what he calls Lansdalism. For Boot, who has seen America’s 21st-century wars up close, there is a profound contemporary message in the Lansdale story: the importance of the United States standing for democratic values in conflict zones that verge on civil war and chaos. Lansdale argued consistently for the support of legitimacy defined by some form of democracy. He could manipulate politicians, to be sure, but he thought that American values and interests were served by supporting representative government, clean elections, and basic justice. Like Lansdale, Boot emphatically rejects the notion that counterinsurgency is simply about going and killing the bad guys: Indeed, Lansdale firmly believed that a firepower-heavy approach would be counterproductive in the wars he fought. And Boot believes strongly that although the bureaucracies of the CIA, the State Department, and the armed forces have become far more hostile to the maverick type than they were in the 1940s and 1950s, the United States needs to make room for more Lansdales in public service.

This is the part of the book that will attract controversy. Some argue, for example, that the counterinsurgent’s job is solely to isolate or destroy the opposition, while others contend that the United States is simply too incompetent to conduct the nation building that Lansdale and his biographer think is essential. (A perceptive young Harvard professor named Kissinger who visited Vietnam in the early 1960s saw that the conditions for success in the Philippines in the late 1940s and in Vietnam in the mid-1950s no longer existed a decade later in a war that had become overwhelmingly conventional.) Still others will point to Lansdale’s failure (which he anticipated) in Operation Mongoose to suggest that the costs of employing such unorthodox means directed by unorthodox characters outweigh their benefits.

There is much to be said on both sides. What is indisputable, however, is that the United States is not done with unconventional war in fragmented societies and chaotic states, and whether Lansdale provides the model or not, anyone who takes that policy problem seriously has to read this exceptionally fine and engrossing biography.

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