Chicago Blues, Book 2 of the trilogy Medicine for the Blues Jimmy Harper arrives in Chicago with the Diggs Monroe Jazz Orchestra, seeking fame and fortune. Instead he descends into the jazz underworld where he becomes entangled in dark dealings with a sinister mob boss and in an erotic affair with a black drag performer. In this unfamiliar world, Jimmy begins to question whether he can trust anyone, even his old band members. The trilogy Medicine for the Blues explores the complexities of gender and sexuality through the historical lens of the early 1920s. Chicago Blues follows Book 1 Acquaintance. The story continues in Book 3 Dangerous Medicine.