This chapter explores the relationship between the Communist Party USA (CPUSA) and the Communist Party of Puerto Rico (CPPR). It addresses how the two parties understood and acted upon the obvious power imbalance between them. The Comintern and Communist parties throughout the Americas advocated an end to colonialism. Yet, the CPUSA was the Communist Party of the nation that colonized Puerto Rico. This chapter will examine how these contradictions and challenges affected the development of the CPPR and the relationship between the two parties.