Neil McCauley, a career criminal, hires Waingro to help him rob $1.6 million in bearer bonds from an armored car. During the heist, Waingro impulsively kills a guard, infuriating McCauley. When his crew, Chris Shiherlis, Michael Cheritto and Trejo, attempt to kill Waingro, he escapes.

McCauley, despite having a strict code: "in your life that you cannot walk out on in thirty seconds flat if you spot the heat around the corner," strikes up a relationship with Eady (Brenneman). His fence, Nate (Voight), suggests he sell the stolen bonds back to their original owner, money launderer Roger Van Zant (Fichtner), who could profit by claiming the insurance on the bonds. Van Zant agrees, but instructs his men to ambush McCauley at the meeting. McCauley survives the ambush, killing both of Van Zant's men, and vows revenge against Van Zant, threatening him by telephone.