This paper traces the root causes of the Macao Special Administrative Region (SAR) government's inability to regulate the city's major economic issues. This regulatory deficiency can be partly attributed to the city's 500 years of Portuguese colonial rule, although some of the problems have been caused by the casino boom, which began with the liberalization of Macao's gaming industry, and the government's failure to cope with ensuing dramatic changes. From a historical and institutional perspective, the author illustrates and analyzes the dynamic relationship between economic regulation and urban politics on a rapidly growing urban island facing various governance challenges.