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Starring in this epic drama set in the high stakes world of espionage, Matt Damon plays Edward Wilson, an exceptionally bright and talented son of privilege who is recruited from the campus of Yale University to join the Office of Strategic Services, the precursor to the CIA, at the beginning of World War II. Wilson's acute mind, spotless reputation and sincere belief in American values render him a prime candidate for a career in intelligence, as do his deeply embedded commitment to honor and quite secretive nature. As Wilson becomes a veteran operative in counter-intelligence during the Cold War, not even his wife Clover, played by Angelina Jolie, nor his beloved son Edward Jr., can divert him from a path that will force him to sacrifice everything in service to his country.
A 20-year CIA vet is convicted of spying and is sentenced to 23 years in prison, becoming the highest-ranking officer convicted of espionage. After leaving behind a failed Army career and while in a state of depression, his youngest son begins to seek solace and advice from his father who is in an Oregon federal prison. The father raises his son's spirits but also coaches him in spycraft, in effect launching a second act of espionage from behind bars by using his son as a courier. In the ensuing year and a half, the son travels the world selling secrets to the Russians, all the while getting deeper and deeper over his head.