Sweet Evening Breeze (1895-1983), born James Herndon, was a well-known LGBTQ figure in twentieth-century Lexington, Kentucky, whose gender identity defied categorization at the time. While she wore men's clothing and answered to her birth name at work and church, she was Sweet Evening Breeze in her personal time, during which she dressed as a woman. As a Black individual living through the Jim Crow era, she achieved a rare level of visibility and influence, becoming a fixture in the city's social and political life. Despite the cultural constraints of the Old South, she formed relationships across institutions of power, including the mayor, local police, university athletes, and members of the regional elite, challenging conventional ideas of who could access and exercise influence.

This book traces the life and legacy of Sweet Evening Breeze, examining her place at the intersection of race, gender, and power in the American South. Drawing from archival records, oral histories, and cultural analysis, it explores how she navigated a deeply segregated and gendered society while maintaining a public presence and exerting her influence on local culture and politics. Rather than seeking to define her using contemporary terms, this work focuses on the specific roles she played, and how her story complicates dominant narratives of Southern history, LGBTQ identity, and Black experience in the twentieth century.

Sweet Evening Breeze (1895-1983), born James Herndon, was a well-known LGBTQ figure in twentieth-century Lexington, Kentucky, whose gender identity defied categorization at the time. While she wore men's clothing and answered to her birth name at work and church, she was Sweet Evening Breeze in her personal time, during which she dressed as a woman. As a Black individual living through the Jim Crow era, she achieved a rare level of visibility and influence, becoming a fixture in the city's social and political life. Despite the cultural constraints of the Old South, she formed relationships across institutions of power, including the mayor, local police, university athletes, and members of the regional elite, challenging conventional ideas of who could access and exercise influence.

This book traces the life and legacy of Sweet Evening Breeze, examining her place at the intersection of race, gender, and power in the American South. Drawing from archival records, oral histories, and cultural analysis, it explores how she navigated a deeply segregated and gendered society while maintaining a public presence and exerting her influence on local culture and politics. Rather than seeking to define her using contemporary terms, this work focuses on the specific roles she played, and how her story complicates dominant narratives of Southern history, LGBTQ identity, and Black experience in the twentieth century.