Puerto Rico’s Olympic representation at the Central American and Caribbean Games serves as a window not only to see nationalism, but also to observe and analyze colonial, imperial, and regional political interests. For Puerto Ricans in the 1930s, at stake in Central American and Caribbean Olympism was the meaning of the nation, the terms of colonialism, the uses of Olympic diplomacy, and the limits of insular authority. The political, economic, and social instability of the 1930s occurred alongside accomplishments in Puerto Rican Olympism, allowing, along the way, a brief but profound moment of national pride and colonial compliance. That is to say, the success on the athletic field fed the growing belief in the nation, and since this occurred under a colonial relation it portrayed the U.S. regime as a “benevolent empire.” Therefore, what is special about the Puerto Rican construction of national identity is that it was carried out in a colonial context. In fact, these early “national” delegations ambivalently represented both Puerto Rico and the U.S. Puerto Rican delegations were sent to represent the U.S. in order to foster Good Neighbor policy and as a bridge between Anglo and Latin America. To be sure, Puerto Rico is not the only place where sport and colonial politics collide. C.L.R. James’ classic Beyond a Boundary (1963) pioneered this process for his native Trinidad and British imperialism. Yet, Puerto Rico presents a different case, one that is pertinent to the Spanish Caribbean in its relation to Latin America and to the U.S. Empire.