The Good Shepherd is a bold, ambitious, but ultimately unsuccessful attempt at staging an American epic around a clan of WASPs who come of age in the late 1930s. This clan is not made up of cousins and other kinsmen, a la The Godfather, but brothers of privilege who first learn the value of keeping one's mouth shut during pee-on hazing rituals for Skull & Bones. The secret-handshake games these tight-knit young men practice at Yale will be put to the test when war against Germany leads to the hasty creation of a foreign intelligence service, and Uncle Sam comes looking for the best and the brightest -- "Jews, Catholics and Negroes need not apply." Luck graces one of the chosen few, Edward Wilson, (Matt Damon) when his college professor is discovered to be moonlighting as a covert Nazi organizer. Ousting the professor from the shadows brings Wilson to the attention of the right people, who put him on a track that will nurture his secretive side and eventually saddle him with the secrets of a nation.
Wilson is supposedly a composite of James Jesus Angleton and at least one other forefather of America's intelligence community, but factual bona fides are not a priority here. The film's energy isn't really devoted to exploring why and how the CIA came into being, but to solving surface-level mysteries about double agents -- there's even a running attempt to decipher the clues in a piece of audio/video, Mission Impossible-style. The large roster of characters includes a Kim Philby turncoat figure, played by Billy Crudup, who floats in and out of the piece seemingly at random. There's also Wilson's CIA handler, played by Robert De Niro, whose job involves looking solemnly at whoever he's talking to and saying things like "You won't be able to trust anyone," which in the movies usually translates to "I'm a spy." These characters and others in The Good Shepherd run up against an enormous time compression that's been unwisely forced on the picture. An original running time rumored to be well over three hours has been compacted down to something closer to half of that.