In Chicago, a Robin Hood-like crook is an object of affection, nice to some and not so nice to others.[2]
Chicago mobster boss Shep Morrison (Cesar Romero), who has a reputation as a brutal killer, falls for department store employee Judy Miller (Virginia Gilmore) on Christmas Eve. Learning that Miller's job is to babysit children for shoppers, the unmarried Morrison presents himself to her as a widowed father in the banking industry, and hires her to help with his children. Morrison quickly dispatches his henchman Frosty Welch (Milton Berle) to find children to pose as his. Welch returns with only one child, Detroit Harry, Jr. (Stanley Clements). As Miller helps Morrison decorate his Christmas tree, he mentions that his other child is with grandma for the holidays.[3]
Thugs Puffy (Frank Jenks) and Louie (Marc Lawrence) interrupt the happy scene, upon orders from rival crime boss Pretty Willie (Sheldon Leonard) to kill Morrison. Rather than kill them, Morrison and Welch lock them in the basement. Pretty Willie arrives the next day and is convinced Morrison has killed Puffy and Louie. The two mob bosses reach a gangland cease fire agreement to conduct their criminal activities in different areas.[3]
By now, Miller realizes who Morrison really is, but he smooths thing over by getting Miller a job as a vocalist in the nightclub, and by agreeing to watch over Harry, Jr. She realizes she has fallen in love with him in spite of his criminal activities, and accepts his marriage proposal. It is soon revealed that Morrison has never killed anyone, when the thugs escape from the basement. Morrison makes newspaper headlines when word leaks out that he's a mob boss who has never murdered his rivals.[3]