This biographical study features the leadership of Joan Miller Wint, now retired, who for 23 years was principal of Denbigh High School, located in a high-poverty rural area in Jamaica. In the article I examine biography as a qualitative research strategy used in "telling" the stories of women leaders; explore the influence of Wint's early life and education on her leadership; highlight the challenges Wint encountered as a principal, as well as how she transformed the school from low-performing to high-performing; and discuss Wint's story in terms of the themes in the scholarship on women's leadership.