In 1847, Cherokee and Choctaws in Indian Territory raised over $800 to help victims of famine in Ireland. Their donations were part of one of the earliest instances of transnational disaster philanthropy, and Cherokees and Choctaws were extremely unlikely donors. Just over a decade earlier they had forced off of their lands in the American southeast and marched west along the “Trail of Tears.” These events cost much in both property and lives. In the aftermath of this trauma, American Indians found the resources – both monetary and emotional – to give to a suffering population an ocean away. While many American commentators considered these contributions as evidence of the success of missions to “civilize the Indian,” this article argues that these philanthropic acts should be read neither as acts of acculturative generosity nor as unconnected and unique charitable outbursts. Rather, I see them as engagements with American political culture, as ways to comment on missionaries’ projects and to engage with American Indian policy. These donations were products of intersecting loyalties, sympathies and animosities that grew out of parallels between Indians’ experiences at the hands of the American government, and Irish experiences at the hands of the British government. The Cherokee and Choctaw donations exemplified a new set of meanings that came to be ascribed to philanthropy in the nineteenth century. This article positions Native philanthropy as part of a constellation of familiar, but nonetheless deeply political practices that those excluded from formal politics were able to deploy in nineteenth-century America.