In Prohibition era Chicago, bootlegger Frank Sinatra as Robbo and his cronies refuse to pay greedy Guy Gisborne (Peter Falk) a cut of their profits after he kills mob boss Big Jim. When Big Jim's daughter Marian (Barbara Rush) gives Robbo $50,000, believing he has avenged her father's death, the gangster donates to an orphanage, cementing his reputation as a softhearted hood. Robbo finds it useful to have the public on his side and invites director Allen A. Dale (Bing Crosby) to join his gang, having him handle all the charities. As Robbo's joint reopens, he is framed for murder and must clear his name with the help of Little John (Dean Martin), Will Scarlet (Sammy Davis Jr.), and a surprising change in public opinion.
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