This History of Education Society Presidential Address primarily utilizes evocative autoethnography and narrative inquiry to convey its main points. It is written in the storytelling tradition of the African American past and analyzes the lives of three generations of Black Mississippians as they navigated life in Jim Crow Mississippi. It highlights the impact and legacy the cotton economy had on the life opportunities of these Black Mississippians, and how the cumulative stories they shared within the family directly shaped the educational pursuits and outcomes of a present-day descendant.