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Youth mentoring has evolved to become a popular youth development strategy. The Obama administration has catapulted the idea of mentoring youth of color, especially men and boys of color, into the mainstream with the My Brother’s Keeper initiative. However, much of this mentoring does little to address the social, political and economic contexts minoritized and marginalized youth exist within. Quantitative knowledge of these contexts is available but mentoring processes have yet to address these contexts; which involve levels of racial, social and economic toxicity. If mentoring is to aid opportunity and equity, praxis must be developed that can address this toxicity. The author suggests "critical mentoring," a mentoring process informed by critical race theory, to bring knowledge into action.