My dissertation is a political and cultural history of seventeenth-century Anglo-Algonquian New England. Between the Pequot War of 1637 and King Philips War in 1675-76, a covalent Anglo-Algonquian society existed in New England. This created conditions which allowed the Pequots to reconstitute their communities after the devastation of the Pequot War. Robin Cassacinamon was instrumental in this process. His skills as an interpreter, diplomat, intermediary, and community leader connected Cassacinamon to the surviving Pequots and to important regional Algonquian and Puritan figures of the time. Cassacinamon became Pequot sachem, leading his people until his death in 1692. His work provided the Pequots with essential tools needed for long-term survival as an identifiable people: a land-base and the ability to form and maintain Pequot communities. Cassacinamon and the Mashantucket Pequots navigated this conflicting political climate to pursue their own agenda. The period between the Pequot War and King Philip\u27s war provided a finite window of opportunity by which Cassacinamon could exploit the seventeenth-century Native strategies outlined in Eric Spencer Johnson\u27s work. These strategies included alliances, marriages, settlement patterns, coercion, and others. Cassacinamon\u27s deep ties to the Pequots and other Algonquian groups, as well as with the Winthrop family and other colonial leaders, let him exploit various political and social tools. Cassacinamon\u27s skills made him an essential part of regional negotiations between these Algonquian and English polities. By operating in the gaps and intersections where these polities met, Cassacinamon and the Pequots carved out a place for themselves within the regional social and political power structure. By focusing on Cassacinamon\u27s story, a greater understanding of how the Pequots survived after the Pequot War is reached. Cassacinamon\u27s biography also broadens our understanding of this seventeenth Anglo-Algonquian society, as well as what happened when the Anglo-Algonquian frontier shifted to an Anglo-Iroquoian frontier after King Philip\u27s War. Thus, my dissertation is not just a biography; it is a political and cultural study of New England, with broader Atlantic World elements. It provides insight as to how an indigenous North American population exploited overlapping political and social systems and tactics to survive in a changing colonial world