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The Good Shepherd is a 2006 American spy film produced and directed by Robert De Niro and starring Matt Damon, Angelina Jolie, and De Niro, with an extensive supporting cast. Although it is fictional, loosely based on events in the life of James Jesus Angleton, it is advertised as telling the history of the birth of counterintelligence in the Central Intelligence Agency (CIA). Edward Wilson (played by Damon), a senior CIA officer, discovers a mole in his department following the disastrous Bay of Pigs invasion in 1961. The film delves into Wilson's complex life, starting from his college years at Yale University in 1939, his initiation into the Skull and Bones fraternity, and his recruitment into intelligence work during World War II. His personal life is marked by a strained marriage to Margaret "Clover" Russell, played by Jolie, and a series of affairs that underscore the sacrifices and moral compromises inherent in espionage work. The narrative unfolds through a mix of present-day events and flashbacks, exploring the origins of the CIA, Wilson's involvement in key historical events, and the personal toll of a life dedicated to secrecy and intelligence. The film features an ensemble cast including Alec Baldwin, William Hurt, Joe Pesci, and John Turturro, among others. "The Good Shepherd" is a fictionalized account of the early days of the CIA, blending historical facts with dramatic elements to explore the complexity of intelligence work, and its impact on individual lives. The film was released on December 22, 2006, to mixed reviews. It grossed $100 million against an estimated $80 million production budget. Plot In 1961, the Bay of Pigs invasion ends disastrously. Senior CIA officer Edward Wilson is warned there are suspicions of a "mole" in his department. Returning home, he finds a photograph of a man and woman in bed, and audio tapes that have been tampered with, leaving certain details unclear. In a flashback to 1939, Wilson is attending Yale University, and is invited to join the Skull and Bones fraternity. During his initiation, he reveals that he discovered but never read the suicide note left by his father Thomas. He was an admiral who had been pegged to serve as Secretary of the Navy until his loyalties were questioned. FBI agent Sam Murach recruits Wilson to investigate his poetry professor Frederick's ties as a Nazi sympathizer. Once exposed, Frederick resigns. Wilson begins dating Laura, a fellow Yale student who is deaf. After an announcement that World War II has begun in Europe, Laura asks Edward to sleep with her, but stops at the last moment. In 1940, Wilson attends a party and meets Margaret “Clover” Russell, sister of fellow Bonesman John. He is also introduced to General Bill Sullivan, who tells him the US will soon be compelled to enter the war and offers Edward a job in foreign intelligence. Clover, whose father is a Senator and head of the isolationist America First Committee, is attracted to Edward and he eventually succumbs to Clover's aggressive advances. While on a date with Laura at the beach, Edward is approached by John, who tells him Clover is pregnant and implies that Edward is obligated to marry her. Laura, reading their lips, walks away. On Edward and Clover's wedding day, he is presented with orders to leave for London. There he is reunited with Dr. Fredericks, in reality a British intelligence operative who had recommended Edward for counter-espionage training. Special Operations Executive officer Arch Cummings informs Edward that Fredericks' indiscreet liaisons pose a security risk. Fredericks refuses to retire quietly and is killed. In post-war Berlin, Edward collaborates with Soviet counterpart "Ulysses" in the exchange of captured scientists. During a call home, his son Edward Jr. inadvertently reveals that Clover is having an affair. Edward impulsively sleeps with his office's interpreter Hanna Schiller, but discovers she is a Soviet operative. This results in her murder. In 1946, Edward returns home and to Washington, DC to a distant Clover, who has resumed use of her birth name Margaret. The two each admit to having had affairs. She says that her brother John was killed in the war. Edward is again approached by General Sullivan, this time to help create the CIA with colleague Richard Hayes, with Phillip Allen as director. While Edward feels genuine affection for his son, Margaret grows increasingly disenchanted as he continually prioritizes work over family. World tensions are heating up again. While monitoring Soviet activity in Central America, Edward receives an agent’s severed finger. It is apparent retaliation for the CIA having dumped locusts at a Soviet-fronted coffee company. Valentin Mironov, a high-ranking KGB defector, presents information about "Ulysses" and warns Edward that he expects other men claiming to be him to seek asylum. While attending a play with Mironov, Edward encounters Laura after many years. They begin an affair, but they end it after Margaret receives compromising photographs of them and publicly berates Edward. Another Soviet defector claims to be the real Mironov, accusing the first defector of being a double-agent named Yuri Modin. Tortured and administered liquid LSD, he ridicules his interrogators before hurling himself out a window. The first Mironov offers to take LSD to prove his innocence, but Edward declines. Edward Jr. follows his father's footsteps in attending Yale and joining Skull and Bones. To the senior Edward's surprise, the son expresses interest in working for the CIA. During an argument about this, Edward admits that he does not love Margaret and married her only because she was pregnant. Margaret begs him to protect their son, which he promises to do. US relations with Cuba worsen as communist Fidel Castro comes to power. During another party, Edward Jr. overhears his father, Hayes, and Allen discussing the upcoming Bay of Pigs invasion. Edward realizes his son has heard and reminds him of the extreme importance to remain silent. Margaret tells Edward she is leaving him. In 1961, the CIA conducts deep analysis of the tape recording that Wilson received after the failure of the Bay of Pigs invasion; analysts suspect the photograph he also received was taken in Léopoldville, Congo. Traveling there to investigate, Edward learns that his son is renting an apartment and realizes he is the man speaking on the tape. "Ulysses" appears and plays an un-edited recording in which Edward Jr. reveals the Cuban operation to his lover Miriam. After she is identified as a Soviet operative, "Ulysses" offers to protect Edward Jr. if the father Edward will become a double agent. Edward confronts his son, who refuses to believe Miriam is a spy and has asked her to marry him. Edward discovers evidence that Mironov is a double agent, and Arch Cummings his co-conspirator. Cummings flees to Moscow, while "Mironov" is arrested by the FBI and deported to the Soviet Union, to almost certain.... Discover the Margaret Shepherd popular books. Find the top 100 most popular Margaret Shepherd books.