This dissertation explores the integration of work-study programs, mentorship, and support systems at Cristo Rey Tampa Salesian High School (CRTSHS) and their role in preparing underrepresented students for post-secondary education and professional careers. Utilizing a case study methodology, this research centers on an in-depth analysis of a single participant's experience, which provides a qualitative insight into the impacts of these educational components. The study examines how the school's work-study program equips students with practical skills, how mentorship shapes their academic and personal development, and how support systems contribute to their readiness for higher education and employment. The data for this study were collected through Surveys, interviews, and a thorough review of academic experience. This comprehensive approach ensures a robust understanding of the participant's journey. The findings unequivocally demonstrate that CRTSHS's model significantly enhances college readiness and employability, fostering a well-rounded individual capable of effectively navigating post-secondary challenges. The implications of this study underscore the substantial promise of community schooling models, when integrated with robust work-study programs and active mentorship, in reducing educational inequities and preparing students to be successful contributors to the economy. This research significantly contributes to the broader discourse on educational strategies that support underrepresented populations. It provides compelling evidence to guide future implementations of similar educational models in diverse contexts, enlightening the academic community on effective strategies for addressing educational inequities. [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.]