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This paper, based on an oral history study on experiences of Puerto Ricans in the diaspora, surveys the history and impact of colonial oppression and circular migration. Participants describe liberatory educational experiences that interrogate oppression and focus on one’s history, one’s relationship to their family, community, and the world at large. The ravages of neoliberalism, poverty, xenophobia, ableism, sexism, anti-blackness, homophobia, the school to prison pipeline, and other forms of violence towards students in our schools bring us to a crisis point that necessitates an understanding that education in a plural, democratic society should not be a project of assimilation and subjugation but an undertaking where students grow to know and understand history and love their complex and intersectional identities.