The primary goals of this qualitative case study were to analyze and evaluate the perceived benefits of a mentoring program on Latino mentees, mentors and school culture. A secondary area of interest was that of the interpersonal and programmatic dynamics that presented themselves during the implementation of a mentoring for urban Latino high school students. Data collection instruments included interviews, observations, questionnaires, journals and program documents. The findings suggest that mentors perceived the programmatic features of training, monitoring and Mentor Mingles as being very supportive of their mentoring role. Mentor qualities that fell into the Trust Theme, Personal Concern Theme, and Approachable Theme were considered to be very effective in building positive relationships with the mentee. The study found that there were four significant challenges that faced this mentoring program: time, financial resources, recruiting mentors and the building and maintenance of effective mentor/mentee relationships. Additionally the study found that Latino students had many perspectives on how to improve their high experience and build school culture. Implications for practice include ensuring that mentoring programs are built around programmatic features that constitute best practice; making mentors aware that certain qualities are more effective in building quality relationships with the mentee; developing strategies for the challenges of time, recruiting mentors, financial resources and building and maintaining effective mentor/mentee relationships; and developing the schools ability to assess school culture among certain student populations. Limitations of this study included the researcher's role as headmaster, researcher bias, small sample size and the relatively brief study time. Recommendations for future study include monitoring the mentored Latino students and reporting on their graduation rates, conducting an additional study with a control group of Latino students who do not have the benefit of participating in a mentoring program, studying the impact of family configurations as they relate to the success of the mentees, an analysis of the mentor's age and success of the mentoring relationship, a similar mentoring program study on a different ethnic group, and a study and analysis of students mentored by teachers as opposed to non-teachers.