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The Supreme Court’s historic decision in Plessy v. Ferguson (1896) established constitutional legitimacy to Jim Crow segregation laws in the public sphere. Undeniably the judicial response is most often viewed through a legal lens, which demonstrates the law’s role in constructing and maintaining racial categories in a white supremacist formulation. However, what is often overlooked is considering the role of legal education and the network of people and activists behind the Plessy case. This paper explores the law department at an integrated historically Black college and university (HBCU), Straight University, and it chronicles a group of prominent Afro-Creoles in post-Reconstruction New Orleans. It revealed how these men leveraged their legal education in an activist frame to formulate the Plessy challenge.