As the largest and fastest growing racial/ethnic group in the country, Latinos' educational success is a national priority. In the Los Angeles Unified School district, the country's largest, high school graduating rates for Latinos hover at near 40%. Examining this institutional and societal tragedy through the school-to-prison pipeline has yielded crucial insights. Less understood are alternatives to the school-to-prison pipeline and the vital role of educational leaders. This qualitative study of principals and counselors in Southeast Los Angeles schools asks: What is the relationship between the 'school-to-prison pipeline' and the lacking of a 'college going culture' in underserved communities? How do educational leaders perceive their role in creating a "college-going culture" in largely underserved, under-resourced communities? Among the findings is the continued existence of deficit explanations of school failure and the need for school-community partnerships to move toward more asset- based frameworks.