William Frederick Billy Klair (1875-1937) was the undisputed czar of Lexington, Kentucky, for decades. As political boss in a mid-sized, southern city, he faced problems strikingly similar to those of large cities in the North. As he watched the city grow from a sleepy market town of 16,000 residents to a bustling, active urban center of over 50,000, Klair saw changes that altered not just Lexington but the nation and the world: urbanization, industrialization, and immigration. But Klair did not merely watch these changes; like other political bosses and social reformers, he actively participated in the transformation of his city. As a political boss and a practitioner of what George Washington Plunkitt of Tammany Hall referred to as honest graft, Klair applied lessons of organization, innovation, manipulation, power, and control from the machine age to bring together diverse groups of Lexingtonians and Kentuckians as supporters of a powerful political machine. James Duane Bolin also examines the underside of the city, once known as the Athens of the West. He balances the postcard view of Bluegrass mansions and horse farms with the city’s well-known vice district, housing problems, racial tensions, and corrupt politics. With the reality of life in Lexington as a backdrop, the career of Billy Klair provides as a valuable and engaging case study of the inner workings of a southern political machine.