This chapter addresses the case of Hannah Elias who labored in New York’s interracial sex trade and became the mistress of one her white customers, John R. Platt. When their affair was exposed to New York residents, the eighty-four-year-old businessman charged the thirty-nine-year-old black divorcee with extorting from him over $685,000 between 1896 and 1904. While the charges leveled against Elias suggested criminal activity, the court testimony revealed the contours of a consensual seventeen (rather than seven) year-old interracial relationship and the complex trajectory of a poor, fair-skinned black woman from Philadelphia who eventually became, for some, a rich, racially-ambiguous New York homeowner and businesswoman. In order to prove that Platt had willingly engaged in their relationship and supported her financially rather than being blackmailed into paying her, Elias understood that she needed to reveal the trajectory of their intimate liaisons. Defying the stock image of the sexually deviant black woman prevalent in popular culture and white society, Elias articulated this narrative without regard for public censure. Her unapologetic revelations about her “low life” as a poor woman, sex worker, entrepreneur, and mistress provide a unique opportunity to explore how one turn-of-the-twentieth century black woman publicly framed the story of her sexual behavior. Elias’s story was her own; she refused to be defined as victimized by a powerful white man. By doing so, she left a set of sources that disrupt how the larger society scripted her and, instead, defined her own flawed truth.