This chapter presents a portrait of Herbert Hill, who identified himself as “an unreconstructed abolitionist.” As labor secretary of the National Association for the Advancement of Colored People (NAACP), he was a combatant in a war against men and women who, by history, politics, and religion, should have been in his camp. Hill was a brilliant and determined crusader who made the most of the limited legal remedies available against workplace discrimination in the 1950s and 1960s. He brought actions before the National Labor Relations Board to decertify unions that violated the nondiscrimination provision in federal contracts, and he carried cases against both labor unions and employers to state antidiscrimination commissions. Hill consciously fashioned this employment rights campaign after the larger NAACP fight to dismantle de jure segregation and discrimination in education, housing, and at the ballot box. He drafted an effective and widely distributed NAACP Labor Manual that described the complex gamut of discrimination tactics in the workplace and advised African Americans that the NAACP was ready to aid them in their fight against such inequities.