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In 1941, John Cusack, a U.S. Navy Intelligence agent, is sent to Shanghai to investigate the truth behind the assassination of his friend Connor. Disguising himself as a German journalist, he navigates the social circles of Shanghai's elite. By leveraging his relationship with the wife of a Nazi engineer, he manages to gather intelligence while avoiding suspicion. During a gambling session, he meets Anna, the wife of the gangster Lan Ting (played by Gong Li), whose mysterious code words with her subordinates pique his curiosity. Unable to follow her directly, he continues his inquiries. To uncover the reason behind Connor's death, he secretly meets one of Connor's informants. However, their meeting is disrupted when the Japanese military begins investigating underground activities. By chance, Cusack meets Anna again, and through her introduction, he meets the Shanghai crime boss Anthony Lan Ting (played by Chow Yun-fat) and the Japanese intelligence officer Captain Tanaka (played by Ken Watanabe). As the investigation unfolds, Cusack gradually discovers that Connor's death is linked to a mysterious Japanese woman (played by Rinko Kikuchi)...