This essay uses the lens of the "preferential option for the poor" to examine the unprecedented turn to poverty by religious movements in late twelfth and early thirteenth-century Western Europe. Three movements are selected from the many and various movements espousing poverty: the Humiliati, the Waldensians, and the Franciscans. The Humiliati developed a communal lifestyle that, in key ways, reflected the emerging urban working class. The Waldensians embraced a radical poverty that rejected all forms of property, but they were progressively marginalized from Catholicism and eventually became targets of the Inquisition. The Franciscans adopted a very similar sort of radical poverty, but their communities ultimately would be assimilated into mainstream Catholicism. The essay places these movements into a dialogue with the contemporary notion of the "preferential option for the poor" in order to discover the ways they might inform and illuminate one another.