After a long and arduous trip to the Northwest where he battled “superstition” and “savagery” with the civilizing words of God, Jesuit missionary Father Pierre Jean De Smet’s convictions remained more resolute than ever. Mulling over his missionary efforts, he concluded, “The Blackfeet, especially, have something hard and cruel about their features. You can read in their faces words written in blood. There is hardly one innocent hand in the whole nation. But, of course, the Almighty can bring forth sons of Abraham from the hardest of rocks.” De Smet’s determination to convert the western tribes to the Catholic faith represented not only a daunting task, but one fraught with uncertainty. While a few authors have dealt with the conversion of the Blackfeet to Christianity, scholars have ignored the ambiguity of relations between the Blackfeet and the Black Robes. Many analyses have taken a limited approach to a key question of Christianization: God or the Great Spirit? A lack of scrutiny on this core inquiry—whether God meant something, nothing, or something different for the Blackfeet—has obscured our historical understanding of the confrontation between the tribe and the Jesuits. Historical inquiries have failed to address fully another crucial issue: whether the tribes’ connections to Christianity were syncretic or pragmatic, a combination of new and old beliefs or a decision based on practicality. In essence, did their actions in the presence of the Jesuits reveal “cultural brokerage,” or rationality, or both? The keys to unraveling this puzzle lie in the symbolic language and acts of the Blackfeet themselves. The answers reveal a cultural dexterity far beyond what the Jesuits expected or recognized. While some tribes, such as the Flathead, took more quickly to Catholicism, the devotion of the Blackfeet proved much more difficult to develop. For the Jesuits, the Blackfeet took on a dual nature. The missionaries saw them as worthy converts, while describing them as cunning, conniving, and evil. A vision of the Blackfeet as Christian soldiers conflicted with the reality of their violent warfare against other tribes. This duality and the uncertainty of the Jesuits’ views of the Blackfeet colored every interaction between the two, ultimately contributing to a Christianization effort that fell short of its designed intentions.