Over the course of five years (1919-1924) the Newton Boys, a group of brothers, were the most successful bank and train robbers in North America, traveling from Texas to Toronto without ever firing a fatal gunshot. Willis Newton (Matthew McConaughey is the eldest brother who is determined to improve the fortunes of the family by becoming a "businessman" whose business is bank robbing. With the rationale that all banks are insured insurance companies being the biggest crooks the brothers begin their spree. By 1924, they executed the biggest mail train robbery in American history, stealing 3 million dollars from a train in Rondout, Illinois (a Chicago suburb). All goes smoothly until Brentwood Glasscock (Dwight Yoakam) accidentally shoots Dock Newton (Vincent D'Onofrio). Going against the odds, they decide to take Dock to a doctor. The court trial that follows sees the boys and their partners sentenced to prison.