Casino capitalism has its dialectical tendencies in Macau. On the one hand, it stimulates economic growth, provides employment, and strengthens the post-colonial state in Macau during the period of economic boom. On the other hand, casino capitalism can widen the income gap between the rich and the poor, generate addictive gambling, and de-legitimize the post-colonial state in Macau during the global and regional economic downturn. The weaknesses of the politico-administrative state in Macau, including the absence of institutional checks and balances, the frail civil society and the relatively docile mass media, have magnified the negative impacts of casino capitalism on Macau. In response to the negative ramifications, the Macau government has taken measures to be more interventionist, to enhance social welfare, and to prepare contingency plans that would tackle the sudden bankruptcy of any casinos. The central government in Beijing also displays contradictory considerations when it deals with Macau’s casino development, supporting the casino industry while simultaneously encouraging the Macau government to diversify its economy. Overall, casino capitalism not only has contradictory impacts on the Macau city-state but also reveals the inherent contradictions of Beijing’s policy toward the territory’s over-dependence on the casino economy.