When New York City police officer O'Malley learns of a young man who is about to embark on a life of crime by taking part in a robbery, he takes the boy aside and tells him the story of Boomerang Bill, another wanna-be gangster who wanted to be a big shot in the New York crime scene. It seems that Bill fell for a pretty young dance-hall girl, and went up against local gang boss Tony the Wop when he insulted her. Tony, who never forgot a slight, found a way to make things very, very tough for Boomerang Bill, in a way that he never saw coming.

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