In light of Judith Butler’s insight, including her theories of gender trouble and performativity, this article investigates Brazilian journalist and activist Fernando Gabeira’s trajectory against machismo, homophobia, and gender presumptions. That trajectory spans his formative years, in Minas Gerais (1940s and 50s), the armed resistance to the military dictatorship. in Rio de Janeiro and São Paulo (1960s), the activism during exile, mostly in Sweden (1970-1979), and another 35 years of sociopolitical engagement, after his return to Brazil. Key to this essay’s central inquiry are Gabeira’s thoughts and experiences in his O que é isso, companheiro? (1979), O crepúsculo do macho (1980), and Entradas e bandeiras (1981).