Written by Eric Roth, The Good Shepherd is the story of Edward Wilson (Matt Damon), a well-heeled Yalie who is recruited into the intelligence-gathering Office of Strategic Services (OSS) two years before Pearl Harbor and ultimately rises to become our nation's chief spymaster at the height of the Cold War in the 1960s. Jumping around in a complicated two-decade period of international history, Wilson's life is a narrative of unchosen moral retreat. The young man we meet in college has an ear for poetry and a sense of dignity. He stands up to the advances of a professor in the position to assist his academic career. His undoing, however, commences when he accepts membership in the secretive but widely influential fraternity Skull and Bones where he only briefly resists but ultimately submits to humiliation in order win acceptance. From that point forward Wilson's life is a series of compromises. Each provides him a step up on the ladder of career advancement, but he pays for each with a piece of his soul.
Wilson's private life provides a mirror for his professional rise. He holds honor and loyalty as the greatest of virtues. But he proves very agile in defining both in ways that serve his career. When he impregnates a young woman (Angelina Jolie), he agrees to marry her, even though the two barely know each other. Of course, the fact that she's a senator's daughter and the sister of an early OSS operative obviously opens doors for Wilson that might otherwise have remained closed. When a mentor in the OSS is denounced as a security risk, Wilson manages anguish but no action as the man is murdered. Such sacrifices have to be made for the good of the nation. Or so Wilson manages to convince himself.
The Russian-American alliance in World War II very quickly collapses into mutual suspicion and surrogate struggles for territory that mark the long, scary Cold War. Anti-communism rather than a more flexibly defined sense of national interest dominates the American political thinking of the day. We think more clearly about who we are against than what we are for. If the Congo elects a leftist like Patrice Lumumba, we choose ideology over democracy, and Lumumba is murdered. When Castro rises in Cuba, we join forces with the Mafia in trying to kill him. If spies, or men we deem spies, won't talk, we torture them. The well-being of the nation requires it.
The Good Shepherd is long and complicated and requires concentrated viewing. Unfortunately, it also expects an audience more knowledgeable about the details of Cold War history than it's likely to get. How many viewers can recall the events of the Bay of Pigs, what this invasion of Cuba hoped to accomplish, why it failed and how it led to the Cuban missile crisis a year and a half later? Pivotal events in this movie are set in the Congo in 1961. But how many contemporary moviegoers can articulate American interests in central Africa a half century ago? The movie is more affecting and stimulating for those who can than those who can't.
Pointedly, Roth and De Niro make Wilson a bureaucrat rather than an ideologue, and Damon renders him as a chin-down, slump-shouldered trudge of a gray man. And in this way he stands for all of us. Wilson makes narrow choices rather than broad policy. His craft is one of compromise. And in the end, he has compromised so much that there's nothing left of the idealism that originally drew him to national service. Men like Wilson brought us the Vietnam war, failed to learn the lesson of our humiliation there and lived on to steer us into the mess of Iraq. As Pete Seeger asked during the era this film depicts, "When will we ever learn?"