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The second wave feminist media, defined as ideological contributions via the written word, played an essential role in the second wave by sharing radical ideologies and bringing women into a feminist consciousness. This study examines the herstory of three groups in Boston at the time: the Second Wave magazine (1971-1983), the Combahee River Collective (1974-1980), and Persephone Press (1976-1983). Each group had different motivations yet remained dedicated to the radical feminist media and various methods of societal upheaval. As a radical feminist magazine, a black feminist organization, and lesbian-feminist publishing house respectively, the women behind the three entities aspired to alter the face of second wave feminism. Each had several commonalities: including a commitment to the feminist media, factionalism and ideological strife, difficulties in balancing beliefs with harsh systemic realities, and a great connection to coalitions and the greater feminism community. The Second Wave, the Combahee River Collective, and Persephone Press may appear conflicting at first glance but shared a great commitment to facing sexist oppression through the written word.