While robbing a bank in Liberty City, ambitious criminal Claude is shot and betrayed by his girlfriend and accomplice Catalina (Cynthia Farrell) Although he survives the wound, Claude is arrested and sentenced to ten years in prison. While being transported in a prison van, Claude and fellow prisoner 8-Ball (Guru) are inadvertently freed after an attack on the police convoy, and escape to a safehouse.
8-Ball later introduces Claude to the Leone Mafia crime family; Sex Club 7 owner Luigi Goterelli (Joe Pantoliano), Don Salvatore Leone (Frank Vincent), his Capo Toni Cipriani (Michael Madsen), and the Don's son Joey Leone (Michael Rapaport). During work for the family, Claude finds himself fighting the Colombians, who are being led by Catalina in proliferating a new drug. Meanwhile, Salvatore's trophy wife Maria (Debi Mazar) begins to take a liking to Claude. Salvatore grows suspicious and betrays Claude into luring him to a death trap, but Maria saves him just in time and they both flee]
Claude then begins working for the city's Yakuza and its leader Asuka Kasen (Lianna Pai), Maria's close friend, who has Claude assassinate Salvatore and get his revenge. This cuts off all of Claude's ties with the Leone family, who are now against him. Claude's work leads him to allying himself with other criminal sources, such as corrupt police detective Ray Machowski (Robert Loggia), an enemy of the Cartel. Claude later saves him from Internal Affairs and the CIA by helping him flee to Vice City.
Claude also meets charismatic media mogul Donald Love (Kyle MacLachlan), who maintains a huge media front. In an effort to start a war between the Yakuza and Cartel, Claude and Love organise the death of Asuka's brother Kenji Kasen (Les Mau) and blame the Cartel. Later, Love asks Claude to rescue a man who was kidnapped by the Cartel in the prison truck that Claude was in. While on an errand, Claude finally confronts Catalina, who narrowly escapes. Asuka abducts Catalina's partner Miguel (Al Espinosa), believing him to have knowledge of her brother's death.
With the war with the Cartel intensifying, Asuka and Maria learn of Claude's history with Catalina and order him to attack many Cartel operations.
Eventually, his exploits attract the attention of Catalina. As a result, the Cartel kidnap Maria, murder Asuka and Miguel, and demand Claude to pay a $500,000 ransom in exchange for Maria's release. When Claude confronts Catalina, she attempts to have him killed, but he escapes. In the resulting firefight, Catalina attempts to flee in a helicopter and makes a final attempt on Claude's life. After killing the remaining Cartel members and rescuing Maria, Claude shoots down the helicopter, effectively killing Catalina. As they are leaving the scene, Maria complains to Claude about the kidnapping, particularly the state of her clothes and nails. During the credits, a gunshot is heard, and Maria's voice is silenced.[b]
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