This qualitative study examined the motivating factors and barriers of Native American male students acquiring postsecondary education. This study sought to understand the similarities and differences between motivating factors and barriers as they corresponded to their decisions to attend or not attend college. Further, key issues regarding the motivating factors and barriers for attending and completing college were examined. The major motivational factors were support and encouragement from family. The primary barriers were lack of funding and transportation. From a Tribal Critical Race Theory perspective, this study brought to the educational leadership field the structural inequalities related to programmatic and leadership in secondary and higher education institutions for Native American males. Findings suggested programs need to be developed assisting Native American men to make a successful transition from high school to college. [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.]