This essay challenges the image, popularized by Henry Louis Gates Jr., of eighteenth-century African American poet Phillis Wheatley “on trial” before a jury of eighteen white male judges. Brooks argues that there was no trial and that Wheatley instead made her career by cultivating an intricate network of relationships to white women. Because Wheatley crafted elegiac and occasional poems for her white female auditors in exchange for their support, these women exerted a disproportionate influence over the shape of her published Poems (1773). Their participation in this transactional, sentimental culture of mourning enabled white women to indulge feelings of self-consciousness, self-regard, and willful passivity imbricated with their increasingly privileged merchant-class status. It also allowed white women to evade taking responsibility for their economic privilege—a privilege capitalized on the unfreedom of enslaved men and women like Wheatley—and ultimately to evade their responsibility to the poet herself. This essay, then, explores the racialized and gendered dynamics of sentimentality in eighteenth-century American literature as well as their continuation in late twentieth- and twenty-first-century feminism.