The leadership regarding gambling in Evansville, Indiana lacked a zeal to achieve what was good for the community on a long-term basis and gave in to the appeal of immediate gratification. The phenomenal emergence of gambling was not an overnight occurence; it did not grow into the largest industry in America by chance or without challenge. The success of gambling in American and Evansville, Indiana was the result of a process requiring leadership. In Evansville there were many different types of leaders, ranging from state and local politicians to wealthy casinos and landowners as well as ministers and concerned citizens. The followers were the voters who allowed these leaders to influence their vote. This paper briefly examines several leaders who played a role in the process and what type of leadership qualities they utilized. Were their choices based on principles or tactical maneuvers? Were they seeking long-term benefits or immediate gains? This paper also seeks to succinctly establish a premise of what leadership is and how it should be used. This examination concludes that the leaders achieved success in bringing riverboat gambling into Evansville but questions whether it really was in the community's best interest over the long-term. Leadership based on principles and core values may have established a different outcome. Finally, this capstone project as a thesis in Liberal Studies, is intended to be more of a commentary on the leadership involved in bringing riverboat gambling to Evansville rather than a traditional research paper.