During the Constitutional Convention of 1890, one delegate characterized the history of county formation in Kentucky as a process whereby "fifteen or thirty or forty people" created "outrageous special legislation" to make laws that "were not for the benefit of the people at large, but only for the benefit of people who were to be enriched by them" (Kentucky Constitutional Convention 1890, 395). The legislative history of the early years of both Owsley and Lee Counties finds the process described by the delegate to the Constitutional Convention of 1890 clearly at work. Self-interested individuals shaped the legislation that created Owsley County. These elites subsequently relied on their ability to obtain special legislation from the state legislature in order to manipulate Owsley County to their benefit. Their influence on the legislation was so obvious that members of the McGuire family, or their associates, were often mentioned by name within the text. Though armed with numerous pieces of legislation, the McGuires and their allies were unable to dominate Owsley County politically. They ultimately responded to their setbacks in Owsley County by creating Lee County. In doing so, they sowed the seeds of the pervasive poverty that grips Owsley County today. In this article, the author describes the role of the McGuires and their allies in the formation of the 19th-century politics in Kentucky Counties.