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Postsecondary attainment is often viewed as an accomplishment yielding financial, social, and economic gains. Moreover, education has been a passport to a better quality of life. However, certain populations are often hindered from achieving these aforementioned goals. In particular, Black males are viewed from a deficit perspective, especially when it comes to excelling and achieving in the sphere of education. The authors discuss the collaborative role of school psychologists and school counselors as change agents in the college and career readiness of Black males. Specifically, the authors present an innovative approach to using a culturally responsive multitiered system of support that infuses Critical Race Theory to address the negative postsecondary outcomes Black males encounter. School psychologists and school counselors are appropriately trained to implement this model; therefore, recommendations for policy, practice, and research are provided in this article.