This essay argues that the 1623 starving time through which Pilgrims championed universal self-interest was a direct and anticipated consequence of their risky decision to build a palisade and a fort rather than plant corn. This historical insight, derived by comparing Edward Winslow's Good News from New England with William Bradford's Of Plymouth Plantation, updates and advances literary historical assessments of the power of sympathy in a settler colonial context. First, it reveals how the figuratively boundary-blurring fellow feeling that was exemplarily required by New England settlers' social theory had its historical conditions of possibility in the prior construction and renewal of material boundaries—walls, forts, and fences. These boundaries affirmed difference both within and beyond the New England settlement, and they normalized the self-interest across which sympathy's transgressive power derives. Second, these readings demonstrate not only how fellow feeling was enabled by these material demarcations but also how expressions of sympathy, particularly through practices of mercy, violently intensified the social difference that these walls and fences represented. This violence was at once explicit—in the terror and torture enacted on indigenous people—and implicit—in the expectation that fellow settlers forgo their desires for justice in the name of an affectionate community. Finally, in reviewing fellow feeling's capacity to be used as a weapon, this article suggests how future scholarship in New England studies might participate more robustly in a critique of the settler colonial conditions that endure into the present.