This chapter examines the process by which Puerto Rican nationalists engaged with the Olympic Movement in their struggle for decolonization. Sotomayor shows not only shifting meanings of colonial Olympic sport for nationalists, but, more generally, that the Olympic Movement has been used and serves as a platform to negotiate nationalism and decolonization. Thus, this chapter displays the intricacies of colonialism, nonsovereign nationalism, and decolonization struggles within the Olympic Movement in the Caribbean.