Despite ongoing efforts to improve retention and engagement of Black Males in postsecondary education, there remain significant differences in academic achievement compared to other racial demographics. This qualitative research study examines the effectiveness of a "Culturally Strategic Mentoring" (CSM) approach that provides Black Males with better tools for academic retention and engagement at public institutions. Twenty-four black male undergraduate students were selected to participate in this pilot mentoring program at three different college campuses utilizing nine professionally trained mentors as a means of providing ongoing support for two consecutive semesters. Preliminary results indicated that engagement, retention and grades were improved, as well as developing coping strategies specifically aimed at challenges facing Black males in public postsecondary education in California.