This paper focuses on the island city of Macau as Europe’s last Asian colony and one of China’s special administrative regions (SARs) that enjoys a high degree of autonomy. The author traces the root cause of the current social discontent and political dilemma in the face of Macau’s post-colonial casino boom and economic miracle. The study finds that Macau’s islandness, smallness and geographic location significantly affect the island city’s urban political culture. While Macau shares similarities with other island cities across the world, as a Chinese casino city under Portuguese administration for more than 400 years, certain unique features have also developed.