In 2018, Macau will celebrate the 20th anniversary of its return to China. The past few years have witnessed brilliant economic achievements as well as a structural shift toward a gaming-industry dominated economy. Following so many years of rapid growth, it is essential to take stock of both the benefits and costs of gaming industry development. Accordingly, this paper analyzes the evolution of Macau’s gaming industry between 1999 and 2016, and evaluates the industry’s effects on local economic growth and urban development. As the paper shows, Macau has exhibited many of the symptoms typically associated with booming sectors in small economies, and has witnessed the similar effects widely experienced by western casino cities. However, Macau is also faced with some unique challenges, regarding its geographic location, size constraints, and political factors. These findings illustrate the difficulties that have accompanied Macau’s economic achievements, but also call attention to opportunities in the next phase of Macau’s development.