This paper examines the evolution of regulatory and business structures of the casino industry in Macao in the context of its current rapidly changing legal and economic environment. This analysis discusses the interaction between legislative change and the evolution of Macao’s casino industry from the middle of the nineteenth century to the present. The role of institutions, the process of institutional change and their interrelationships with the industry’s performance in both the short and the long run are examined. Models are developed to explain the relaxation of formal constraints that permit the main stakeholders to maximize economic rents within the historic and current context of Macao casinos. The paper also discusses some of the business practices and regulatory challenges that will confront Macao’s casino industry in the years ahead.