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Some canonical works explaining the over-representation of Black Americans in the carceral system have emphasized their unique history with slavery. This paper explores this legacy by investigating both the presence of comparable levels of disproportional imprisonment in Canada, and the relationship between racial history and contemporary imprisonment. I compare the disproportional incarceration of seven ethno-racial groups across all American and Canadian jurisdictions (states, provinces, territories). After finding equivalent levels of disproportionality in both countries, I seek to evaluate the weight of a broader legacy of racial repression as a predictor for this disproportionality. Using a mixed-methods approach, I first conducted comparative-historical research to generate an ordinal variable for this legacy – combining archival data on slavery, legal segregation, and de jure voting restrictions – to capture the extent of formal barriers to equal citizenship for each group-jurisdiction in the sample. I then present regression models to test the effect of this legacy on contemporary imprisonment in contrast with other prominent explanations. I find that histories of racial repression robustly predict higher disproportional imprisonment for groups, with no systemic difference between the two countries.