In 1931, Captain Steven Warren, the chief investigator for the Chicago District Attorney's office, tries to arrest the henchmen of notorious gangster and bootlegger Roger Touhy for a series of crimes, but the frightened witnesses refuse to cooperate. Warren releases Touhy's cohorts--Herman "Owl" Banghart, Bernard "Troubles" O'Connor, Icebox Hamilton, Maxie Sharkey and Thomas J. "Smoke" Reardon--from custody but vows to pursue them. In Dec 1933, after Prohibition is repealed, Touhy decides to go "straight" because he is tired of pressure from Warren and the police. Needing money to buy a brewery, Touhy asks businessman Joseph P. Sutton to repay the $200,000 that he owes him. Although Sutton has the money, he claims that he does not, and his partner, Edward Latham, advises him to stall Touhy. Fed up with waiting, Touhy and his men kidnap Sutton and eventually collect $70,000 ransom from Latham. After Sutton is released, Warren pressures him to identify Touhy's gang as the kidnappers, and the reluctant businessman finally does so, although he does not reveal his prior connections to Touhy. While Touhy and his men are leaving the area, they are involved in a minor automobile accident that leads to their arrest. During their trial, Smoke testifies against Touhy and the others, who are found guilty and sent to serve ninety-nine-year sentences in the Stateville Peniteniary at Joliet, Illinois. Touhy is infuriated by Smoke's betrayal, and as the next eight years pass, continually tries to obtain a new trial. Smoke, who has been in hiding, is caught by some of Touhy's followers on the outside and framed for a crime he did not commit. Smoke is then sent to the penitentiary, and after being terrorized by Touhy, agrees to recant his testimony and help to free the gang. Smoke is killed by another prisoner before he can talk, however, and a desperate Touhy plans to escape from the prison. With the help of a prison guard, Touhy and his cellmate, George Carroll, escape along with Owl, Troubles, Icebox, Maxie and Rowden, another prisoner. Because the United States is now involved in the war, Touhy knows that the men will be arrested if they are caught without draft cards, and so orders Carroll and Rowden to rob unsuspecting citizens of their cards. The Federal Bureau of Investigation then takes over the case, as Touhy and his men have violated the Selective Service Act, first by not notifying the draft board of their "change of address," and then through their theft of the draft cards. Maxie's drunken carelessness causes Touhy to beat him viciously, and after Maxie and Icebox leave the gang, Icebox is arrested and informs the police of Touhy's whereabouts. Soon after, Rowden and Carroll are killed when F.B.I. agents attempt to apprehend them. Working with Warren, the F.B.I. then surrounds the apartment where Touhy, Troubles and Owl are living, and Owl convinces Touhy to surrender quietly, telling him that it is now time to pay for being on top for so long. Touhy and his men are then returned to Joliet.