A body of research suggests that a significant number of academically and intellectually gifted Black male college students have been psychologically and emotionally drained by the constant, insidious marginalizing they have experienced in their elementary, secondary, and postsecondary educations. Studies also present examples of predominantly White institutions (PWIs) of higher education with cultures that not only lack inclusivity but have also produced such high levels of racial stress on Black students that they experience a lasting sense of systematic exclusion. On the other hand, there are also multiple generations of Black male students who were able to successfully navigate the complex cultural landscape of PWIs. In some cases, these individuals often paid an emotional and mental cost, but they were able to overcome the normal obstacles and challenges of being a college student as well as the additional pressures of attending a PWI that had not originally been accessible to students of color. This dissertation adds to the body of research on the experiences of Black male college students across generations and poses the question, How have the educational experiences of Black male students and the culture of the predominantly White institutions they attended changed from the baby boomer generation to the millennial era? This multiple case study examined research participants from both generations as well as archived data from a state institution and a private college in the northeastern United States to address this question. Findings from this study suggest that the ability of a Black male student to navigate a PWI culture may be influenced by a range of factors including previous experiences in predominantly White environments as well as his socioeconomic status rather than generation or institution type. [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://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]