This dissertation demonstrates the contingent and contextual nuances of Islamic legal history by balancing precise legal case studies with broad-spectrum jurisprudential surveys. This work places Islamic legal history within diverse late antique (seventh to tenth centuries CE) and medieval (tenth to fifteenth centuries CE) contexts through specific comparisons with rabbinic legal traditions. By delineating intricate legal changes involving several generations of jurists, my research demonstrates the flexibility, expansiveness, and contingency of Islamic legal traditions within a meta-narrative about the transformations of law in the "Near East." I offer a historical understanding of the ambiguous and mutable nature of law and illustrate the complexity of legal pluralism and the struggle for legal-politcal authority that underlies the formation of orthodoxy. This research challenges common reifications of "Islamic law" as an inevitable outcome or a static, monolithic whole.