This Article examines racially gerrymandered school districts at the turn of the twentieth century in North Carolina as an ugly yet hopeful apologue for modern districting policy. Before the turn of the twentieth century, educational expenditures for black children in the state were surprisingly close to expenditures for white children, at least in part due to state-constitutional litigation establishing that taxes paid by whites must fund black schools. Yet by 1910, expenditures for black children were half those for whites. This Article first highlights the role diminished black political power and consenting courts played in allowing localities to gerrymander their way around the state constitution’s requirement for racially integrated school funding. Within creatively-drawn school districts, localities could raise tax rates, apply the increased funding to white schools, and avoid allegations of unconstitutional funding segregation. Gerrymandered districts thus became a turnkey system for discrimination that helped result in explosive growth in educational inequality. This Article then draws lessons for modern gerrymander litigation based on how litigants in North Carolina collected, represented, and persuaded courts to use quantitative data to confront inequality.