Jefferson Davis and Stephen Douglas both identified closely with the Mississippi River Valley, which they envisioned as the core of a sprawling continental empire. By situating them in time and place, this chapter illuminates their ambitions and ideals. Davis, born in Kentucky in 1808, moved to Mississippi as a child and, after a stint in the army, established himself as a cotton planter during the booming years of the mid-1830s. Born five years later in Vermont, Douglas moved west in 1833 and relished the upward mobility afforded him in Illinois. As hotbeds of agrarian capitalism, Mississippi and Illinois shaped Davis and Douglas’s clashing visions for the future. Life as a cotton planter confirmed Davis’s unyielding devotion to slavery—and to making its preservation a national priority. Douglas’s early experiences in Illinois shaped his determination to banish slavery from public debate and focus instead on territorial conquest, infrastructure, and other policies calculated to hasten the development of a Greater Northwest that sprawled from Chicago to Puget Sound.