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Carrie Lacey's happy upbringing is seemingly immune from the pressures of growing up Black in rural South Carolina during the Great Depression. But life changes when her mother and six siblings are forced from their Anderson home, leaving Carrie and her father, Hallie.
While working for White businessman Tommy Joe Butler-a bootleg liquor dealer-Carrie becomes aware of the depth of her father's campaign to change the lives of African Americans. He is using some of the strategies of the Underground Railroad, the nonviolent system of freeing slaves in pre-Civil War America. Her childhood friend, Nappy Eddie, attempts to keep the truth from Carrie, but to no avail. When Butler and Hallie continue to disagree over property ownership, she departs Anderson in frustration.
During her travels, Carrie encounters her alter ego, Dicie Caughman, commencing an odyssey that spans nearly eighty years and numerous locales. Carrie, in the form of Dicie, lives a good life, though marked with deep-rooted secrets.
The Bootlegger's Mistress embodies the essence of The Great Migration-the decades-long movement of six million African Americans from the racially oppressive South to the economic opportunity-laden North during much of the twentieth century.