Portland, Oregon, is celebrated in the planning literature as one of the nation’s most livable cities, yet there is very little scholarship on its small Black community. Using census data, oral histories, archival documents, and newspaper accounts, this study analyzes residential segregation and neighborhood disinvestment over a 60-year period. Without access to capital, housing conditions worsened to the point that abandonment became a major problem. By 1980, many of the conditions typically associated with large cities were present: high unemployment, poor schooling, and an underground economy that evolved into crack cocaine, gangs, and crime. Yet some neighborhood activists argued that the redlining, predatory lending, and housing speculation were worse threats to community viability. In the early 1990s, the combination of low property values, renewed access to capital, and neighborhood reinvestment resulted in gentrification, displacement, and racial transition. Portland is an exemplar of an urban real estate phenomenon impacting Black communities across the nation.