Wilson—whose deeply closeted homosexuality is cagily suggested but never confirmed, and makes a dubious motivation for his obsessive secrecy—hooks up with a good-hearted deaf woman (Tammy Blanchard) before being forced to marry a fellow Skull's pregnant sister (Angelina Jolie) with whom he's shared a campfire-lit clench. At that point he hightails it to Europe, where he works undercover for 11 years, helps lay the foundation for the CIA, witnesses his first state-sanctioned murder (of a friend, no less), and thoroughly alienates his family. Things really fall apart when he returns home, however, and unwittingly involves his grown son (Eddie Redmayne) in the planning of the 1961 Bay of Pigs debacle.
Screenwriter Eric Roth (Forrest Gump, Munich) and De Niro work hard to establish a compelling aura of arcane paranoia and compulsive obfuscation, and for the first hour or so largely pull it off. But Don DeLillo's Libra this movie is not—in fact, it's not even Oliver Stone's JFK, despite the estimable participation of that film's cinematographer, Robert Richardson.
For all its torpid indignation over the hollowness of spookery as a way of life, The Good Shepherd indulges in more than its share of espionage antics, particularly in a wraparound sequence positing the mysterious double-cross that botches Wilson's Kennedy-sanctioned 1961 raid on Cuba. It's disappointing that The Good Shepherd relies on such unlikely plot twists to provide its few narrative jolts, although its relative dearth of violent set pieces is a relief; what little bloodshed there is generally occurs off-camera. That doesn't excuse the heavy-handed mopiness that passes for psychic violence, however—the story ought to be oozing it, but instead there's just Damon's curious, flat-affect hybrid of Tom Ripley and Jason Bourne, for whom we're encouraged to feel sorry. Even worse, decades of spy spoofs have rendered the screenplay's jargony mumbo-jumbo absurd regardless of its historical accuracy. Such lines as "there's a stranger in our house" (to denote the presence of a leaker) and code-names like "Mother" are thus inadvertently hilarious, and one half-expects Get Smart's Agent 99 to turn up.
This po-faced self-seriousness is the movie's downfall and contributes to its relentlessly glum tone, punishing repetitiveness and far-fetched, unsatisfying climax (a harrowing scene involving young Wilson's fiancee notwithstanding). Give De Niro credit for attempting to do justice to a timely subject—the co-option of democracy by a cabal of sociopaths—but about the only thing to be gained from rendering it with as little humor or feeling as its protagonists is tedium.