Richard Peddie is the former president and CEO of Maple Leaf Sports & Entertainment (MLSE), the parent company of the Toronto Maple Leafs, Toronto Raptors, and Toronto Football Club, among other assets. In this interview, Peddie reflects on his career, which started in the consumer packaged goods industry and concluded with leading one of the most successful sport organizations in the world. While emphasizing the importance of leadership skills, he advocates meritocracy, and the application of vision and values and strategic planning to increase enterprise value. Sport management students, scholars, and practitioners can benefit from the experiences and insights that Peddie openly shares in this interview.