Research indicates Latino males are under-represented in the educational pipeline and administrative ranks of public education. Further studies attribute the Latino culture as contributing to the obstacles encountered in Latino advancement. This qualitative study was a life history of a first generation U.S. born Latino raised in a Texas-Mexico border town by his Mexican born mother. Using the combination of LatCrit and Resiliency Theories to frame the study, the research question examined the experiences of a first term Latino superintendent to understand how his attitudes, beliefs and behaviors were affected in his upbringing, how they influenced his navigation of the educational pipeline and how they contribute to his leadership of a majority-minority school district along the Texas-Mexico border. Through the in-depth interviews conducted with the primary participant and the contributions of secondary participants, data was analyzed by using Narrative Coding, Descriptive Coding, Value Coding, and InVivo Coding (Saldana, 2013) wherein the themes of family, support systems, and personal resiliency were identified using the participant's voice and own words. The key findings demonstrate the participant's trajectory and successful navigation through the educational pipeline were determined by the use and interplay of social capital and cultural capital (Monkman, Ronald & Theramene, 2005, p. 12). [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.]