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When Pedro Albizu Campos, president of the Puerto Rican Nationalist Party (PRPN), was released from Atlanta Federal Penitentiary in 1943 Earl Browder, General Secretary of the Communist Party USA (CPUSA) and U.S. Congressman Vito Marcantonio welcomed him in New York City. In this paper I examine the complicated relationship between the PRPN and the CPUSA and Communist Party of Puerto Rico, which was closely aligned with the CPUSA. The fundamental questions I will address are the following. In a colonial situation, such as that of Puerto Rico vis-à -vis the United States, what are the politics of a left-wing political party? Are being revolutionary and leftist the same thing in an anti-colonial struggle? How did the changing politics of the COMINTERN and by extension the CPUSA and CPPR, which evolved from insurrectional to the Popular Front, affect both organizations’ relationship with the PRPN? In order to answer these questions, I draw upon FBI documents, memoirs and writings of members of the PRPN, CPUSA, and CPPR, prison records and trial documents, and media coverage.