For decades, educational and political leaders have grappled with the challenge of closing the achievement gap and providing educational equity for students in all segments of education. Despite legislative mandates on the federal, state, and local levels, the achievement gap stubbornly persists throughout the educational system. The purpose of this study was to conduct a process and outcomes-based program evaluation of a high school to college transition program for African American and Latino males at a large urban community college. A combined evaluation method was conducted to measure both qualitative and quantitative data. The process evaluation measured qualitative data which were the perceptions and experiences of the student participants and chaperones. The outcomes-based evaluation examined student satisfaction with program activities, effectiveness of program processes and activities, program's influence on student understanding of higher education options, and academic performance measured by grade point average, retention, and persistence. The study also examined differences in perceptions and achievement between African American and Latino participants to determine if there was a significant difference between the two groups. The evaluation included analysis of data from approximately 250 eleventh and twelfth grade African American and Latino males and 14 chaperones who attended the program in 1 or more years from 2007-2010. Results from attitudinal surveys, interviews, and one focus group revealed an overall satisfaction with the program related to motivation and inspiration, cultural relevance, program information/activities and program quality as dominant themes throughout the findings. Academic performance data indicated no statistically significant difference in term one and term two retention, persistence, and grade point average between African American and Latino students. Research results from this evaluation revealed the need for institutions to design more intentional precollegiate, outreach, recruitment, and transition programs that include the following components: long-term follow-up; mentoring; financial literacy; resource development; and integrated tracking systems. The results of this research will benefit policy makers, practitioners, and postsecondary institutions with information needed to develop more effective high school to college transition initiatives for African American and Latino male high school students.