In this adaptation of Warden Lewis E. Lawes book, a criminal serving 5-30 is let out on his honor to visit his girlfriend and is executed for a murder she committed.
Tom Connors (Spencer Tracy) arrives on a train amid publicity to Sing Sing. Tom's friend Joe Finn (Louis Calhern) asks Warden Long (Arthur Byron) to favor Tom; but the warden reads his record of assaults with a deadly weapon for which he has been sentenced to 5-30 years, and he burns the bonds Joe gives him. Tom doesn't like the large uniform he is given and slugs a guard. The warden decides to let Tom go without a uniform; but cold soon forces Tom to put it back on. The warden explains how the prison works and will keep Tom in his cell until he wants to work. After three months Tom decides to go on the work pile. Fay (Bette Davis) visits Tom; they kiss, and she promises to visit him twice a week.
Tom and Bud Saunders (Lyle Talbot) are assigned to the shoe factory. At a visit Tom becomes jealous of Fay and Joe. Bud asks Tom if he wants to break out. A man says he is sick and knocks out the guard. Bud shoots a guard; but Tom refuses to go because Saturday is his unlucky day. Bud and two others are still locked in the cell block. Bud shoots another guard, and the warden smokes them out with teargas. Bud jumps to his death. Tom asks the warden to lock his cell. Later the warden gives Tom a telegram that Fay is in critical condition because of a car accident. The warden lets Tom go see her on his honor. Joe learns that Fay wants $5,000 to clear him. A police detective sees Tom and follows him. Fay tells Tom about Joe; she hopes to use the money to help him get out. Tom takes a gun, but Fay begs him to give it back to her. Joe comes in, and Tom fights with him. Fay shoots Joe. The police detective breaks in, as Tom goes out the fire escape. Joe says Tom did it.
The district attorney calls the warden about Tom being charged with murder, but the warden expects him to give himself up. Tom is hiding out and planning to take a steamer. Newspapers criticize the warden, and he writes a letter of resignation; but Tom comes back. Tom is convicted of first degree murder and is taken to the death house. Fay visits Tom. Fay swears she did it, but no one believed her. Tom tells the warden that is not true. Tom tells Fay she could get life and says this is his chance to do something decent. She asks Tom to marry her, but he tells her to find a "square guy." Tom loved Fay more than life.
This story shows a humane warden trusting convicts and almost losing his position because of the political repercussions. A criminal, moved by the warden's trust, sacrifices his life for his girlfriend.