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Puerto Rico is one of the world's oldest colonies, with thousands of its people dislocated to the United States (U.S.) mainland in the wake of Hurricane Maria and the ongoing economic crisis. However, since the 2019 protests ousting then governor Rosello, Puerto Ricans across the Diaspora are imagining new emancipatory realities, including the possibility of independence. This paper draws on data from the Colonial Mentality Study in New York City (CMS-NYC, N = 19) to explore how Puerto Ricans in the Diaspora narrativize new political possibilities despite the challenges posed by post-disaster migration and racial and economic inequality. Using a decolonial psychoanalytic approach, we show how two colonial logics—moving “up and out” of Puerto Rico and “up and in” American capitalism—are textured by discourses of racial inferiority and upward mobility, and illustrate how these are experienced by Puerto Ricans who identify as Multiracial (Multiracial-Identified Puerto Rican, N = 11), and Puerto Ricans who identify as Black (BIPR, N = 8). Reading our findings in the sociogenic context of race, class, and colonialism in Puerto Rico, and race and class among Puerto Ricans in NYC, we explore how racism toward Puerto Ricans and racism among Puerto Ricans intersect with notions of upward mobility, revealing how anti-Blackness supports economic inequality in the U.S. mainland alongside with Puerto Rico's colonial situation. Complementing decolonial psychoanalytic theory with the Afro-Puerto Rican radical tradition, we outline the implications of this research for future scholarship, clinical practice, and political action.