Charlie Barret walks to his private table in a restaurant, only to see two young men sitting at his table – Avery and Max. Another young man who is friends with Avery and Max, Brett, joins them shortly after Charlie sits down and begins chatting with them. Charlie happens to know Avery’s father, and after an initial reluctance, is willing to go with the boys for a “night on the town”.
Before meeting Charlie, they had previously planned to use chloroform to knock him out in their car. The plan goes awry, and Charlie fights back, almost wrecking the car before they can finally put him under. When Charlie wakes up, he sees himself surrounded by the three men, and a fourth friend, T. K., checks his vital signs. It is revealed that Charlie is Carlo Bartolucci, a former mob figure. The boys explain that Avery’s sister, Elise, has been kidnapped, and that the kidnappers are demanding a $2 million ransom for her release. Unable to come up with the money on such short notice, they figure Charlie still has connections to get the money and set up an exchange. To ensure that Charlie knows how serious they are, Charlie is shown his cut-off finger, still wearing his signet ring, as the same was done to Elise. As incentive for his cooperation, they explain that they will do to him everything done to Elise.
Charlie flies into a rage and threatens to kill them, though he eventually agrees to help. As Charlie requests continual alcoholic drinks and his blood does not properly clot, T. K., a medical student, explains that Charlie’s alcoholism may cause him to die of blood loss if he is not taken to a hospital. Charlie contacts his lawyer, who in turn contacts Lono, Charlie’s bodyguard, asking him to track Charlie down. Lono goes about his own investigation, asking for, and in some cases beating out, information from people. However, he shows he has a soft side as one of the people he beats up is the father of Jennifer, the hostess at the restaurant that Charlie and the boys frequent. Meanwhile, Charlie seems to take perverse pleasure in playing mindgames with his kidnappers. During the course of these conversations, Charlie unnerves the friends with stories of his early years as a gangster. Especially concerning some former neighbors of his that hed had killed, then feeding their remains to their Dobermans. Another story was how he got his signet ring.
Meanwhile Marty, Charlie’s attorney, conducts his own investigation. He speaks to Lydia, a successful madam, whose life Charlie had saved, many years ago, from her former lover and pimp. He wanted to kill her because she’d spent money on herself that he felt belonged to him. Lydia gives Marty a list of contacts.
As Lono searches, Charlie takes advantage of the boys’ naïvete. A fifth friend, Ira, shows up unexpectedly and demands an explanation – they are using his house under the cover story of a poker game. Ira is flustered by their carelessness in his parents’ house and becomes even more worried when he realizes they have kidnapped a major figure in the mob. Charlie plays the friends against each other, slowly getting information out of them and using it to his advantage. After much cajoling and piecing information together, Charlie identifies Max, Elise’s boyfriend, as an inside man. As his enraged friends plan to cut off his finger, Avery stops them, admits it was his plan, and says he recruited Max to help him. Avery made several unlucky bets, could not pay off his debts, and was approached by mobsters who had purchased his debt. They offered him a way out: become an inside man in his own sister’s kidnapping.
Lono eventually makes his way to Ira’s house and has Charlie removed from his restraints, around the same time that the money is sent to the two thugs. Avery rushes to meet his sister at the appointed drop-off, but she does not appear. Charlie and Lono track down the two kidnappers, who insist they never kidnapped Elise and the whole operation was a con. Charlie and Lono kill the thugs, and it is revealed that Max and Elise set the whole thing up, splitting the ransom between them and the thugs. Charlie and Lono track Max and Elise to a boat off a tropic island where, although Charlie understands their reasons for conning him and agrees with Max on how special Elise is, he has Lono shoot them both dead. The screen dissolves to a rotoscope red and the film ends.