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In the democratization period following the end of military government in Brazil, the consolidation of the Workers’ Party, particularly in São Paulo, embodies the popular will of conducting politics in a different way. This party especially offers political space to women who succeed in being elected to key positions thanks to the expansion of the rights of workers, traditional populations, and lower classes established by the 1988 constitution. However, the rise of women in the political sphere is not massive and is possibly the result of strong personalities with backgrounds emphasizing the relative flexibility of the Brazilian society, particularly in its largest city, where Erundina de Sousa (1988 - 1992), and Marta Suplicy (2000 - 2004) were elected mayor. Are these victories the result of exceptional conditions or are they indicative of sustainable change?