Scholars of modernism and scholars of feminism have been engaged in an implicit war over Gertrude Stein’s political intentions, and therefore, the reasons for her heroic status in literary and theoretical studies. Recent work in Stein scholarship, which has highlighted this modernist writer’s fascist and anti-democratic sympathies, destabilizes or at least undermines earlier work that demonstrated how many of Stein’s early texts, and particularly Tender Buttons (1914), foresaw feminist and psychoanalytic critiques of language and power. This split in Stein scholarship aligns with other paradoxes in this prolific, generative, and ultimately open body of work--did Stein write for publicity or privacy? Why is there so much evidence that she was and that she was not a feminist? Ultimately the power of Stein’s work is its play with and contestation of received and ready-made definitions: this includes American feminism, both present and past. Unsatisfied with but compelled by the image of the American feminist hero(ine), I argue Stein grappled not only with icons of individual feminists, but the idea of the heroic feminist icon. Literary portraiture, the genre Stein worked and investigated with most consistently, and the genre most ubiquitously used to announce the place and prestige of the hero(ine)—as well as Stein’s own heroic powers of innovation and production— is the site of Stein’s contestation with one visibly recognizable version of the feminist heroine. Drawing from my analysis and theorization of Stein’s portraiture, I argue that Stein sets the temporal movement of language against the visual portrait’s fixity, and therefore undermined ideas and images of a coherent or predictable body. Through her portraiture, Stein worked toward a feminist heroics that works against fixed definitions of the woman’s body and therefore undermines the early goals and assumptions of American feminism. “The Mother of Us All” (1945-46), a late piece in Stein’s oeuvre and a play about Susan B. Anthony, is a testament to this realization. I argue that “The Mother of Us All” offers a better albeit retrospective standpoint for understanding where Stein’s early feminist inclinations and critiques were heading.