Chicago Syndicate (1955) on Netflix

Plot summary

A Chicago newspaper editor, David Healey, and a group of civic leaders want Barry Amsterdam, an accountant and war hero, to go undercover inside Arnold Valent's crime syndicate and open up its corrupt insurance operation. Valent is believed to have had bookkeeper Nelson Kern killed after Kern brought proof of the rackets to the newspaper. Kern's wife then took her own life, and their daughter Joyce was sent to an institution. A $60,000 reward and those deaths persuade Barry to accept. At the Maracas, a nightclub Valent owns, a woman named Sue Morton helps him get inside. There he meets Connie Peters, Valent's girlfriend and the club's singer. Barry tells Valent he witnessed Kern's murder and threatens to take what he knows to the police unless Valent offers him a better deal.