This qualitative research study investigates the multifaceted factors influencing the postsecondary success of historically marginalized Black and Latino male students, with a particular emphasis on understanding the impact of college readiness preparation and persistence. Employing a comprehensive research design, the study integrates semi-structured interviews with high school teachers and counselors, and Black and Latino male freshmen and sophomores to provide a holistic exploration of the challenges and opportunities within the educational journey. Situated within an interpretive phenomenological paradigm, this study elucidates the experiential realities and viewpoints of the subjects, thereby illuminating the socio-cultural, institutional, and individual factors shaping their trajectories in higher education. Through thematic analysis, the research aims to uncover the unique insights shared by both educators and students, highlighting the interconnectedness of their experiences. The primary objective of this doctoral thesis is to ameliorate the gap between theoretical inquiry and practical application by providing actionable guidance tailored for educators, counselors, and policymakers. The aim is to augment college readiness initiatives and bolster persistence rates specifically among historically marginalized Black and Latino male students. By integrating the voices of both students and educators, this research seeks to foster a more inclusive and informed approach to addressing the educational inequities encountered by this demographic. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]