Why is it that colonial America is literally famous today for its array of bridge builders, brokers, go-betweens, middling men and women, but also well known for advancements of racializing divisions and stark forms of collective disempowerment? In the transitional era of early modernity, a large variety of people in North America engaged in processes of transculturation, translation and transfer that had developed from established forms of Christian figural interpretation. These transcultural figurations not only served the trade in new ideas, they also neutralized the trade of disenfranchized people. Gestures of identification and unanimous association accompanied epistemological exercises built on programmatic repertoires and scripts of uncertainty, unreadability, and failure of understanding. The resulting identitarian oscillation between various possibilities of belonging and of distinction soon became constitutive of textual and visual expressions of coloniality and nationality in North America. In this setting, it is especially three recurring figurations that document and inform the implementation of abstract distinctions of religion and race in the Americas: the Native American or African American Christian neophyte, the renegade, and the creole. These figures of thought traversed oceans, centuries, and geographical contexts rather effortlessly, thus establishing connections and continuities where there had been none. The ensuing figural interpretations thrive in an ontological ‘grey zone’ between two and often more than two cultural, religious, political, and social affiliations. They animate an affirmative epistemology of doubt and uncertainty that allowed for various democratizations of the colonial and early national social orders at a rather high price. These figurations normalized and empowered the male and propertied members of white settler communities, while destabilizing the power and the legal claims of indigenous and African people.