Despite his reputation as America’s earliest radical democrat, New England Puritan minister John Wise (1652-1725) has been neglected in the study of democratic and social contract theory. This paper argues that Wise grounds his defense of the people’s power to exercise moral judgement for self-direction in a distinctive theological anthropology. His conception of human capacity for goodness shapes his normative commitment to grace as a model of relational engagement in both religious and political life. Wise demonstrates that the willingness to show grace enables citizens to democratically govern their communities, because it allows them to persuasively exhort one another towards repeated reconciliations that sustain contractual relationships over time. Otherwise, the failure of grace corrupts society’s elites, creating perversions of imperial power that infringe upon local contracts. In this way, Wise demonstrates how grace can maintain affective unity amid political diversity at both the local and imperial level, providing insights about the importance of relational ethics for contemporary democratic judgement.