Iris Apple is like most teens in the 1950s except for two things: She's the granddaughter of Boston's most notorious bookie and she suspects her father murdered her mother. But how can she prove it? The cat and mouse game with her father began on her tenth birthday-the day her mother was gunned down-and tension reigns through her teen years. They live in her family's Kenmore Square rooming house, a haven for Boston's down and outs and where her motherless drama plays out. When Iris turns eighteen, she defies her father and sets out to discover the truth about her mother's demise. Teaming up with Madame Charlemagne, a has-been cabaret singer who lives at the rooming house, Iris learns that a nearby innkeeper holds keys to the puzzle. Instead, she discovers a web of secrets and transgressions that are entangled with hers. Mustering all the courage she has, Iris must unravel the dark webs to bring truth and love into her life.