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Although John Heckewelder (1743–1823) has informed non-Native views of Native peoples in history and literature since his major volumes were published in the early nineteenth century, his writings have not been interrogated for their implicit assumptions. Informed by contemporary disputes about the constitution of a “gentleman” and valuations of Heckewelder’s writings and character, a critical reading of his large corpus of published and unpublished writings reveals resounding anxieties about the viability and moral constitution of gentleman leaders at a time when egalitarianism posed a formidable challenge to elite dominance. The Moravian’s representations of “genuine Indians” and their natural social forms are not disinterested, as he claims, but invested in the genteel culture that contributed to their production. As Heckewelder’s “incontrovertible facts” about the Lenape and Mahican performed the double function of describing Indians and naturalizing the sociopolitical and moral authority of American gentlemen, his credibility was questioned in print reviews that impugned his honor, disinterestedness, patriotism, and racial loyalties. To some degree, his detractors make a point worth pursuing, for the Moravian’s personal correspondence indicates that he was quite adept in dissimulation—as a patriot spy, ethnographer, Indian agent—for personal interest and on behalf of his peers, among whom dissimulation and the careful management of “truth” were accepted practices for acquiring and fortifying cultural capital and social power. Yet the implications of dissimulation prove problematic for Heckewelder. While he privately grapples with his guilt for having violated Moravian pacifist values and engineering warfare that backfired on missions, his publications work vigorously to dissociate missionaries from hybrid frontier populations, whom he relentlessly condemns for inciting violence. Simultaneously, he quietly petitions gentlemen leaders to reform their conduct toward the missions and Indians they have betrayed, lest their immorality prompt an irrecoverable loss of cultural and political authority.