Throughout the nineteenth century Anishinaabeg leaders from the Great Lakes met in treaty councils with U.S. commissioners. Trained for years as astute listeners and eloquent speakers, these diplomats put their skills to the test as they negotiated with their non-Indian counterparts, whose primary responsibility was to serve the interests of the federal government. The stakes were high, for Native territories and lifeways were often at risk. Like most Native nations, the Ojibwe, Potawatomi, and Odawa (collectively known as Anishinaabeg) had long made alliances for purposes of war or peace, but not to formalize a permanent exchange of land. Faced with growing non-Indian demands for land, Anishinaabeg bands negotiated multiple treaties with the United States to maintain their sovereignty, well-being, and place on the land. Although bands regularly crossed borders between the United States and Canada for both trade and social reasons, Anishinaabeg found that non-Indian governments shaped diplomatic concerns in bands' home territories. As the doctrine and practice of manifest destiny swept through the Great Lakes and beyond, Anishinaabeg within the boundaries of the United States faced a different set of challenges than did their kin in Canada. Anishinaabeg negotiations of both land cession and peace treaties with the United States had long-term consequences for their bands. Council journals recorded the treaty-making process in detail, thus meticulously preserving the words and even the actions of the councils' participants. Although council proceedings no longer survive for all Anishinaabeg treaties, a number of those extant reveal important continuities and shifts in American Indian diplomacy. In this article, the author examines how the negotiation process of the Anishinaabeg leaders have evolved over the years. (Contains 1 figure and 77 notes.)