This article is intended to cast light on the general process of the commercialization of sport by examining that process in Trinidad and Tobago basketball. The authors explore the strengths and weaknesses of basketball’s dominant voluntary structure as well as those of the emerging commercialization of the sport. They analyze the tensions between voluntary and commercial basketball, and the relative advantages of each to different segments of the basketball community. They conclude that neither voluntarism nor commercialization is likely to be able to impose its dominance on the other in Trinidad and Tobago. Therefore, the future of basketball in that country will probably involve the coexistence of a voluntary structure alongside an incompletely developed commercial venture.