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The decades-long praise and bipartisan support of charter schools has shifted in recent years. Issues like high turnover, limited academic gains, neighborhood school closures in Black and Brown communities have forced charter advocacy to rebrand. This case study of the Oakland Unified draws on qualitative data analysis and discourse analysis to examine the evolution of charter school advocacy in relation to the emergence of the portfolio strategy. Findings indicate that charter school advocates have adapted market concepts to respond to growing community criticism, using a sophisticated, yet contradictory and elusive package of initiatives that comprise the portfolio district. Calls for “compromise” bridged new racial justice rhetoric and technologies with familiar allies and strategies from the private sector.