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Chicago gangster Big George Kilraine has placed a $117,000 bet on a football game between Western University and Eastern Tech., which is being played in California. The game will be the last for Henderson Platt, the graduating nephew of Kilraine's lawyer, John Andrews, who plays for Western. Hendy, who is a better student than he is a football player, mistakes his helmet for the ball during a fumble, and Eastern Tech. wins after Hendy "scores" with his helmet. Andrews' irritation with his nephew is matched by Kilraine's glee, and Kilraine promptly calls Hendy and hires him to collect his winnings and bring them to Chicago that afternoon. Investigative reporter Ruth Stevens overhears their conversation, which she then relates to her editor, McQuade. Suspecting that Hendy threw the game, Ruth follows him to the airport, where she changes his reservations to a later flight in order to pump him for information. Ruth gets him drunk, and after he misses the first flight, all other flights are canceled due to bad weather. By now Ruth realizes that Hendy is a bumbler rather than a criminal, and helps him hire pilot Speed Wilson to take them to Chicago. During the turbulent flight, the bag containing Kilraine's money goes through the window and lands in a tree on the grounds of the state penitentiary. When Hendy arrives at Kilraine's office, the gangster refuses to believe his story and charges him with embezzlement. During his subsequent trial, Hendy changes his plea from not guilty to guilty just as the judge is about to acquit him for lack of evidence. As he is being taken away, Hendy explains to Ruth that he wanted to be convicted so that he could search the prison grounds for the money and thereby prove his innocence. As Hendy settles into life at the prison, he sees a newspaper column with Ruth's byline entitled "My Day with a Dope," which chronicles her adventures with Henderson "Dope" Platt. Hendy is angry when Ruth comes to see him later, and refuses to listen to her explanation that she quit her job after McQuade began writing the column. Wanting to irritate Ruth, Hendy tells her that he has found the money and is going to keep it. Ruth is worried by Hendy's tough-guy act, and afraid that he might be in real danger, she goes to Kilraine for help. Kilraine dismisses her, but after realizing that he needs to keep an eye on Hendy, he has two of his mugs, Feets and Casino, sent to the prison on trumped-up charges. Hendy confesses to them that he does not have the money, and once again, Ruth interferes. She announces over the public address system that a $10,000 reward is being offered for the money's return, causing everyone in the prison to begin searching. Ruth dons prison garb and joins the others in the yard, where "Old Timer," a prisoner who will not be released until 1987, confides that he has the money. After Ruth tells Hendy about Old Timer, Hendy enlists the aid of Feets and Casino. An impromptu football game, with the money bag as the ball, ensues and ends when Hendy manages to throw the bag to Kilraine outside the prison walls. The money is not inside, however, for it has been confiscated by "Nutsy," an Internal Revenue Service officer who has been pestering Kilraine for back taxes. While Nutsy explains the situation to Warden Bingham and Kilraine, Hendy and Ruth are oblivious to the chaos and hide in a bush to kiss.