Tifanni Devereax, a young, naive African American girl from middle-class Philadelphia, runs away from home to pursue her life-long dream of becoming a model. Raised on the streets by three transsexuals, Tifanni grows from an innocent girl into a cold, calculating, and manipulative woman.

Years later, having achieved fame and fortune, she returns to Philadelphia. When she learns that her deceased husband has left her a diamond importing business, she's overjoyed. But there is one stipulation: before Tiffani can inherit the business, she must make amends with the three transsexuals who helped raise her.

Tiffani has no idea where her friends are, but greed compels her to find them. Immersing herself in the corruption of her previous life, Tifanni reacquaints herself with the habits of her former companions. When she is propositioned by an anonymous man for sexual services, the past suddenly comes back to haunt her. Too soon she returns to those years of depravity and debauchery, and she realizes just how much she's taken her life for granted.

A fable of greed, Daddy's Shrewdest Little Girl is a stunning tale of manipulation, treachery, forgiveness, and the dynamics of loyalty, intimately revealing the dark side of the human experience.