While his brother Bill remains a powerful leader in the Massachusetts Senate, Irish hoodlum James "Whitey" Bulger continues to pursue a life of crime in the 1970s Boston. Approached by FBI agent John Connolly, the lawman convinces Whitey to help the agency fight the Italian mob. As their unholy alliance spirals out of control, Bulger increases his power and evades capture to become one of the most dangerous gangsters in U.S. history.