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Milwaukee, Wisconsin remains among the most segregated cities in the U.S., despite its claim to a longstanding progressive political tradition from socialist mayors between 1910 to 1960. I develop a twentieth-century urban history of Milwaukee to interrogate the outcomes of its socialism, foregrounding black women’s activism that counteracted the effects of city government. This paper investigates the politics of social identity and space in Milwaukee by centering Vel Phillips, the city’s first woman and African American council member, who introduced anti-racist housing legislation and participated in activist demonstrations in the 1960s.