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This critical literature review provides a multilevel understanding of twenty-first century racism and related strengths-based strategies to effectively address the disturbing black male achievement crisis. A critique of contemporary racism literature supports going beyond individual-level bias to also address adverse impacts of multilevel racial bias at meso-organizational and macro-policy levels on Black male educational disparities. Related literature on challenges and strategies in the 21st century reveals five themes: (1) the Black Lives Matter movement’s potential to disrupt color-blind racism, racial apathy and related deficit-based policies; (2) moving beyond model-minority assimilation to racial-caste empowerment strategies to address African American and Afro-immigrant male achievement gaps; (3) addressing racial battle fatigue among Black males in education with multilevel strengths-based strategies; (4) addressing Black male achievement gaps in violent urban communities with innovative African-centered empowerment strategies; and (5) mobilizing critical consciousness among young Black males in culturally-responsive K-12 pre-college pipeline strategies. To better address these challenges in the 21st century, a multilevel strengths-based approach to risk, resiliency and empowerment of African American males is highlighted to guide more rigorous research and effective intervention strategies.