In 2021, the news hit headlines in Canada that the bodies of 215 indigenous children had been discovered at Kamloops residential school in British Columbia. This institution, one of more than 130 such schools in Canada, were federally funded schools run by churches and were sites of systematic human rights violations against indigenous children, aiming to “destroy the Indian in the child” by forbidding cultural expressions such as indigenous language, dress, hairstyle, or visits with parents in a forced Westernization of indigenous children. Similar institutions and practices were active in the United States. And this is only one example of the tragic imperialism and colonialism that has accompanied many Western missionary endeavors. It is thus not without reason that postcolonial scholars, such as Sri Lankan New Testament scholar Sugirtharajah, have condemned not only colonialism but all evangelism and Christian proselytism as inherently oppressive. But does repentance of these atrocities and avoidance of them resign us to this type of pluralism that abandons absolute truth claims for the gospel? Lesslie Newbigin, the missionary and Western cultural critic, provided the resources for the Church to navigate this dilemma. He recognized and articulated the problems of colonialist Western missions, such as those that led to residential schools, as embodying Western chauvinism, imposing Western culture, and characterized by domination and imperialism. Like Sugirtharajah, Newbigin recognized the fundamental ideology lying behind these symptoms as a Western one that defines ideas of “progress” and “development” according to Western ideals and standards and thus frames indigenous cultures a priori as something to be overcome. In response, Newbigin proposed and practiced a model of missions that embodied mutuality between the culture of the missionary and that of the mission field, a faithful contextualization, and an insistence on indigenous leadership. But at an even more fundamental level, he articulated the role of the gospel in challenging all “plausibility structures,” by which he means the grid by which we make sense of all reality. At its core, colonialist mission is the symptom of a confusion of the gospel with a Western, post-Enlightenment plausibility structure and the resulting inability of the gospel to critique Western culture and ideology. This same issue that Newbigin addressed is the fundamental problem of the Church in America, polarized as it is along political lines. Newbigin held that the Church should not be aligned with either the political right or the political left, both of which undermined the role of the gospel in critiquing culture and functioning as the fundamental plausibility structure for the Church. Criticizing both an imposed theocracy by the fundamentalists on the right and the privatizing of Christianity into relativism on the left, Newbigin thus prophetically plotted a via media in which the Church inhabits the plausibility structure of Western culture not in a syncretistic fashion but for the purpose of mission. This paper thus argues that is a way forward in the American Church’s engagement with culture.