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This paper presents a general overview of the challenges faced by English-speaking Black community members in Montreal, as well as the exacerbation of those barriers for individuals with a history of justice involvement. Frontline community initiatives focusing on education, employment, and entrepreneurship at DESTA Black Youth Network are profiled as an example of grassroots efforts to mitigate disparate circumstances between English-speaking Black Montrealers and their white counterparts. Statistical data in the areas of educational attainment, rates of unemployment, and income provide the platform for analysis and, recognizing the multiple identity experiences of belonging to a racialized and linguistic minority, an intersectional framework is employed. Recommendations for more race-based study, policy, and funding to better support equity strategies are provided.