Yitzik "Rick" Baline is a small-time New York criminal during the time of Prohibition. He meets and falls in love with Lois, daughter of Solly Horowitz, a big-time gangster and becomes a favorite of Solly. He eventually becomes Boss of the 'Tootsie-Wootsie' Club, a speakeasy. He is viewed with extreme disfavor by Tick-Tock, Solly's principal assistant, who plans to be the heir to Solly's businesses if he should retire or be killed.

Solly makes it clear that Lois is intended for better things, and she eventually marries a lawyer and would-be politician, Robert Meredith, whom she does not really love.

Warfare erupts between the Horowitz, Salucci and O'Hanlon gangs and there are several deaths. Solly and Tick-Tock are killed, as are Lois and her husband, now exposed as a corrupt politician. Rick must flee America. He takes Solly's money, half a million dollars, probably intended for Lois, and travels to Boston with Sam. While the two are purchasing tickets for a steamship to Le Harve, Rick changes his name to Richard Blaine.