This study sought to explore the leadership styles and theories employed throughout the existence of the National Association for Stock Car Auto Racing (NASCAR). The research examines the decision process and subsequent outcomes, exploring how they ultimately affected the business and trajectory of the sport. NASCAR is the product of unique and specific characteristics of racing enthusiasts who turned their passion into an international empire. This illustrates how leadership styles, specifically dictatorial leadership, successfully managed decisions of the business. Through the use of qualitative research to review historical accounts of events, this study strives to explain how leadership guided the business from small beginnings to a worldwide phenomenon. Data collected included document review, observations, and an interview. Synthesis of the data showed that each of the four primary leaders (Bill France Sr., Bill France Jr., Brain France, and Jim France) used the autocratic/dictatorial leadership style as they directed the sport. Historical evidence shows that this style of leadership was required to build the sport and move it to its current recognized level. Recommendation for further study encourage future scholars to revisit the long-term impact of Brian France’s leadership once more time has passed since his negatively charged removal from the leadership position. Researchers would need to also examine the leadership of Jim France because at the time of this study he has been in his leadership position for less than two years.