The Appalachian region of the United States has been a region surrounded by controversy for the last two hundred years. Many geographic, anthropological and economic studies have taken place in Appalachia to analyze the differing culture and history of poverty. Academic studies in Appalachia, no matter the specific field, tend to apply expertise bias to the region and lack an actual understanding of the culture, institutions and economy of the region. Using The Anglo- Saxons of the Kentucky Mountains: A study in Anthropogeography (1901), The Vanity of the Philosopher: From Equality to Hierarchy in Post- Classical Economics (2005), Inquiry into the Nature and Causes of The Wealth of Nations (1776), Hillbilly Elegy: A Family and Culture in Crisis (2016) and many other sources, the use of stereotypes in Appalachia will be analyzed in relation to their economic effects. How these stereotypes influence exogenous policy (especially economic policies) in Appalachia and the effects of such policies will be used to analyze the use of expertise bias in Appalachia. This analysis is followed by a creative, historical essay which explores my own family’s migration out of Appalachia, focused mainly on my grandfather, Chalmer Combs.