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This paper examines the aftermath of desegregation in one school district and the consequences for racial dynamics and trust. In doing so, the paper addresses the lack of attention to black families’ experiences in special education using data from a year-long ethnographic study in an affluent, suburban school district where disproportionality has been a problem for decades. Trust is a relational social contract, a tacit agreement between parties, involving a calculation of risk and reward on the part of the truster: What do I have to gain from trusting this person(s) and what do I have to lose? With desegregation, black Americans had much to gain, and so they celebrated the Brown decision as a victory and joyously, if apprehensively, sent their children off to school placing both their hopes and trust in white institutions and educators. At the same time, whites mounted fierce and at times cruel resistance to Brown. Thus, the implicit trust that was bound up in desegregation was always a one-sided social contract, because both sides did not agree to the arrangement. Yet for desegregation to work, trust would be essential—on both sides. Black Americans had to place their trust in white institutions and educators and those educators had to honor that trust. I argue that what happened in that critical moment is essential to understanding the crisis in trust that exists today between black and white Americans and affects the risk-reward calculations blacks make with respect to schools and programs such as special education.