Chapter 1 (Parent’s Choice) surveys Indigenous national claims to the northern grasslands in the middle of the nineteenth century, subsequent conflicts with Canada and the United States, and treaty negotiations that set up reserves and reservations. It also surveys the scientific exploration that assessed the land’s agricultural potential. The individuals studied are located within the transnational region through the vernacular literature they wrote, labeled as the pioneer-origin narrative. U.S. and Canadian settler-colonial immigration advanced in three stages from the 1860s to the 1910s and followed an ecological pattern, settling first on the tallgrasses around the region’s outer limits, then moving into mixed-species grasslands from all directions and finally into the northwestern shortgrass center. Settlement of the northern grasslands was entwined and distinctly North American; Canada and the United States developed settler societies together. Arrival stories suggest conflict between these generations and their parents even as they promoted pioneer mythology.