This chapter examines Helen Hunt Jackson as an exemplary figure for the Reconstruction generation of American writers. Nurtured on the sympathetic universalism animating the antebellum realism of Harriet Beecher Stowe’s 1852 Uncle Tom’s Cabin, Jackson collided with the limits of this model at the moment of its triumph. A successful novelist and poet, Jackson became, in the 1870s, an activist for Native American rights. Working across a variety of genres—travel writing published in prestigious magazines such as The Century, the legal history A Century of Dishonor, and the novel Ramona—Jackson attempted to supplement sentimental modes of universalist appeal with legal arguments appropriate to the United States in the era of the Fourteenth Amendment and picturesque representational strategies appealing to a generation increasingly interested in racial, regional, and gender difference. Tracing out Jackson’s affiliation with a variety of contemporary writers, including Mark Twain, Albion Tourgée, and Henry James, this chapter shows how these writings engaged her in a generational rebellion against the high political moralism of the prewar generation. The “sentimental fools,” “sentimental tourists,” and “mugwump aesthetes” of postbellum literature rejected and transformed the sentimental tradition in ways that prepared the ground for a literary field defined by the paired ideals of autonomous literary experimentalism and authentic, pluralistic cultural expression. This chapter argues that Ramona, in its attempt to compromise between sentimentalism and the new epistemological and aesthetic particularity, must be read as an allegory of public agency in an age of violent territorial expansion and divided fields of discourse.