Chapter 6 explores five outlier cases, called “The Unfortunate Five,” in which the US Supreme Court rejected landowners’ challenges to land use and environmental regulations despite the Court’s strong protection of private property rights against regulations generally. These five cases have one factor in common: the developers’ plans to build affordable housing. After exploring the potential that Supreme Court justices are motivated by explicit race and class biases, the chapter delves into the potential for implicit bias to explain why these cases deviate from the norm: the justices believe that they are protecting the private property interests of neighboring landowners against unwanted affordable housing developments. Strategies are proposed, based on a number of empirical studies, for convincing courts that affordable housing does not pose a threat to the property values of nearby landowners and that, therefore, many government policies reflect an unconstitutional, irrational prejudice against low-income people of color who need affordable housing and the developers who seek to build it.