Plot
Shanghai Triad takes place over the course of seven days in the 1930s. The story begins as a fourteen-year-old boy, Tang Shuisheng (Wang Xiaoxiao) has just arrived in Shanghai from the countryside. He is met at the docks by his uncle, Liu, who has sent for Shuisheng to work as a servant for a Triad Boss (played by Li Baotian), also named Tang and a distant relative. Before he meets his new employers, however, he is taken to a warehouse where two rival groups of Triads carry out an opium deal that goes wrong, leaving one of the rival members dead. Shuisheng is then taken by his uncle to Tang's palatial home, where he is assigned to serve Xiao Jinbao (Gong Li), a cabaret singer and girlfriend of the Boss. She mocks Shuisheng's upbringing and derides him as a "country bumpkin." It is soon learned that Jinbao is also carrying on an affair with the Boss's number two man, Song (Sun Chun).
On the third night, Shuisheng witnesses the aftermath of a bloody gang fight between the Boss and a rival boss, Fat Yu. Among the dead are Shuisheng's uncle. In response to this attack, the Boss and a small entourage, including Shuisheng and Jinbao, retreat to a peasants' island. There, Jinbao befriends Cuihau (Jiang Baoying), an unassuming peasant woman who prepares meals for the visitors, while Shuisheng befriends Ajiao (Yang Qianguan), Cuihau's nine-year-old daughter. When Jinbao unwittingly meddles with Cuihua's business, it results in the Boss's men killing Cuihua's lover from a neighboring island. Furious, Jinbao confronts the Boss, who throws her accusations back at her, claiming that had she never meddled, he and his men would have been none the wiser. Jinbao, at this point, reveals to Shuisheng that she, too, came from the countryside. She gives him some silver coins and tells him to start a shop as soon as he is able, away from Shanghai and its depravity.
By the seventh day, Song arrives to the island along with Zheng (Fu Biao), the Boss's number three man. During a mahjong game, the Boss calmly confronts Song with evidence of his treachery. He tells Song that he knew of the younger man's affair with Jinbao and of the fact that Song had been working with Fat Yu to supplant him as king of the Shanghai underworld. The gang kills Song's men and buries Song alive. The Boss then informs Jinbao that she will have to die as well for her role in Song's betrayal. He grants her one last wish in accordance to the "rules," and she asks that he leave Cuihua and Ajiao alone. The Boss goes back on his word and tells her that Cuihua has already been killed for knowing too much, while Ajiao will be taken to Shanghai with him (saying she will be the new Jinbao when she is older). As Shuisheng attempts to save his mistress from her fate, he is thrown back and beaten. The film then ends with Shuisheng tied to the sails of the ship as it sails back to Shanghai with the boss and Ajiao on board.
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