Contextualized in a Western push for post-war decolonization and modernization, the development of recreation programs in 1950s Puerto Rico helped consolidate the state’s sport institution and, in turn, legitimize a new political status. The 1950s was a pivotal decade in Puerto Rican history due to the creation of the Commonwealth in 1952 and the innovative economic project known as Operation Bootstrap. The term “Operation Sport” portrays the development of sport and recreation in this decade as collaboration between the government and the working classes to develop recreational/cultural activities to assuage the impact of dramatic industrialization. However, regardless of the perception of progress, critics targeted the program for its centralization and expropriations, comparing it to “Communist” governments. For the newly established Commonwealth, at stake in the popular acceptance of these recreational programs was evaluation of a new political status arising from promises of social justice.