This chapter explores the complex relationship between Cecil Williams and Strom Thurmond, a prominent figure in South Carolina politics with a history of segregationist policies. Cecil Williams, who once ran against Thurmond in a U.S. Senate campaign, found himself in a surprising turn of events campaigning for Thurmond's reelection in 1995. This endorsement by Williams was a significant and symbolic moment, confounding both Black and White communities. While Thurmond was initially known for his segregationist stance, he had also supported the needs of Black constituents through constituent service, making Cecil's endorsement a multi-layered decision. Ultimately, Williams saw Thurmond as the better candidate between the two. This segment highlights the complexities of political allegiances and the evolving nature of relationships in the realm of civil rights and politics.