Despite the fact that women were barred from voting and holding public office, by 1895 Juana Catarina Romero (1837–1915) had emerged as the major textile importer, sugar refiner, and “modernizing” political boss (cacica) of the city of Tehuantepec in southern Mexico. This article traces Romero’s breathtaking transformation from humble cigarette vendor to culturally assimilated entrepreneur and behind-the-scenes politician, which paralleled and intertwined with three crucial periods of Mexican history: the Liberal Reform, the Porfiriato, and the Revolution. Her life illuminates the many ways in which women participated directly and indirectly in the construction of the nation-state and a capitalist economy, revealing how they negotiated elite efforts at gender, ethnic, and class containment in a provincial setting. The article attributes Romero’s success to her political acumen and tenacious accumulation of economic and social influence and not to a supposed early love affair with Mexican dictator Porfirio Díaz, as previous historians have suggested. Once in power and aligned with Díaz’s goals of “order and progress” and the ideals of social Catholicism, Romero sought to regulate and discipline Tehuantepec, hoping to create a more orderly, productive, and beautiful urban space. Through her influence on Tehuano dress and local fiestas, she attempted to bring local customs into line with the ideals of Porfirian modernization and mestizo identity. Her attention to education, hygiene, health, and urban reforms evidenced her role in the diffusion of national culture and the ideological reproduction of the authoritarian brand of liberalism that dominated Mexico during the Porfiriato.