This article reports on an examination of the relationships between chief executive officer (CEO) personality, transformational and transactional leadership, and multiple strategic outcomes in a sample of 75 CEOs of Major League Baseball organizations over a 100-year period. CEO bright-side personality characteristics (core self-evaluations) were positively related to transformational leadership, whereas dark-side personality characteristics (narcissism) of CEOs were negatively related to contingent reward leadership. In turn, CEO transformational and contingent reward leadership were related to 4 different strategic outcomes, including manager turnover, team winning percentage, fan attendance, and an independent rating of influence. CEO transformational leadership was positively related to ratings of influence, team winning percentage, and fan attendance, whereas contingent reward leadership was negatively related to manager turnover and ratings of influence.