This dissertation argues that emotional experience consisted in diligent effort on the part of the seventeenth century setters of the New England colonies and that this care for fellow-feeling comprised one of the key civic disciplines complementing early Anglo-American settler political life. Literary historians of the early republic and antebellum periods have argued that sentimental literary production manifested and reproduced the ideal political dispositions of the new nation. Earlier colonial literary historians have in turn revealed the precedents of those practices and ideals in the prescriptions for emotional life in the English colonies, particularly within those self-consciously civic-minded settlements of New England. Neither of those discourses, however, have described the phenomenological aspect of sentiment and affection; nor how those were transformed and renewed by the exigencies of the new American continent; nor, finally, how such experience participated in the transformation of emergent power described by historians and anthropologists as modern settler colonialism—a form of power qualified by the ability to make an indigenous population appear to disappear, both materially and discursively. Emotional discipline, I argue, facilitated power’s reformation, and did so with particular intensity in the paradigmatic settler colonial context, the Massachusetts Bay Colony and its nearest colonial neighbors—Plymouth, New Haven, Connecticut and Rhode Island. This study draws on methods of close reading and historically-informed literary analysis to reveal how prescriptions and descriptions of feeling in writing and in speech shaped normative and intimate knowledge of recognizable social bonds. This dissertation reveals furthermore that hostility and aggression characterized all forms of fellow feeling prescribed by the New England settlers—in fact, maintaining these emotionally fortified distinctions between individuals and between groups was one of the most useful conditions reproduced by New England settlement’s self-consciously political revolution in sentimentality and affection. My study concludes that these techniques of prescribing more earnest social feeling endure, inflecting exhortations in the present to “sympathize” with those who seem less fortunate, exhortations amplified in the discourse by which literary analysis tends to justify its existence today.