The dissertation explores the imbricated nature of race, gender, and class in the field of insurance within the political economy of the New South. It considers how enterprising black women navigated tensions between New South rhetoric and Jim Crow reality as well as sexism and racism within the industry and among their industry peers. It complicates the narrative of black southern labor history that focuses more on women as agricultural laborers, domestics, and factory workers than as enterprising risk takers who sought to counterbalance personal ambition and self-interest with communal empowerment. Insurance organizations within black-run secret fraternal societies and formal black-owned insurance companies emerged as not only powerful symbols of black business achievement by the early decades of the twentieth century but also the most lucrative business sector of the separate black economy. Negro Captains of Industry, a coterie of successful, influential, self-made men, stood at the forefront; they represented the keystone of black economic, social, and political progress. The term invoked a decidedly masculinist image of “legitimate” leadership of black business. Considering fraternal and formal insurance, gender-inscribed rhetoric, shaped by racism and New South ideology, imagined black men as the ideal protectors and providers; women became the objects of protection rather than agents of economic development, job creation, and financial security. The dissertation explores how women operated creatively within and outside of normative expectations of their role in the insurance business. The dissertation considers the role of state regulation and zealous regulators who often targeted insurance organizations and companies, the primary symbols of black business success; in other ways, regulation dramatically improved profitability and stability. The dissertation identifies three key periods: the Pre-Regulatory Era, 1890s to 1906; the Era of Regulation, 1907-World War I; and the Professionalization of Black Insurance, Post-WWI to the Great Depression. It also considers the barriers to black women’s involvement in professional organizations. By the late 1930s, enterprising women in insurance lost ground as fraternal insurance waned in influence and as the strongest proponents of the black separate economy promoted a vision that embraced women as consumers rather than business owners. / text