This thesis explores the settlement of the Mississippi Territory through the eyes of John Hailes, a Southern yeoman farmer, from 1813 until his death in 1859. This is a family history. As such, the goal of this paper is to reconstruct John’s life to better understand who he was, why he left South Carolina, how he made a living in Mississippi, and to determine a degree of upward mobility. Local, state, and federal government records provide the general context of this study and accurately track John’s movements and land purchases within the territory. John's frequent movements and the land he bought suggest that he was a herder and relied on hogs and cattle for a living. This contextual biography suggests that John was mobile, that he was sensitive to land policies and market pressures, and that he maintained a yeoman's standard of living throughout his life.