Singapore, with a five million population, has a vibrant charitable sector with over 2000 registered charities attracting approximately USD$2.18 billion in annual donations. How did Singapore’s charitable sector achieve its current level when it has been, in the past, segregated along mainly religious, race and clan-based communities? This paper explores this question by piecing together the current ecosystem, regulatory and tax infrastructure which facilitates the charitable sector in Singapore. Central to the development of the charitable sector has been the Singapore government’s role of being a gatekeeper, regulator and enabler of charities. In analysing the government’s role in the charitable sector, this paper locates Singapore’s charitable sector within the literature on government and nonprofit organization relations which has been described at times being cooperative, complementary, confrontational, and co-optive. These astute observations ring true with respect to the Singapore government’s relationship with the charitable sector. For organizations which pursue purposes consistent with state’s vision of public good, the state’s relationship with these charities has been largely cooperative and complementary. However, even within charities considered by the state to further public good, there is a strong element of co-optation where the state wields significant direct and indirect power over the charitable sector by way of provision of funding and board composition. In contrast, nonprofit organizations which engage in aims inconsistent with the state’s perceived public interest are, by law, unable to register itself as charities and enjoy corresponding fiscal benefits. Such nonprofit organizations also typically do not receive state funding. This demonstrates the confrontational nature of the state’s relationship with these nonprofit organizations. Through a close analysis of the laws, codes, media reports and academic literature on the charitable sector, the central thesis of this paper is that the charitable sector in Singapore is essentially a state facilitated endeavor.