Although the under education of Latino males has not been a priority to many, the high dropout rate of minority males can no longer be ignored. When school principals engage in the practice of cultural collision and collusion, it has an adverse impact on the academic achievement of Latino males and on their decision to drop out of high school. The purpose of this study is to explore the perception of school principals of Latino males, disciplinary policies, and how school principals are addressing the dropout rate of Latino males in their schools; it can aid school policy makers, educational advocates, educators, and parents in better understanding why so many Latino males dropout of school every day. Interviews were conducted on six urban school principals from New York City public schools. Analysis of the interview responses showed that language, poverty, family engagement, and gang affiliations are parts of the Latino culture that could impede their academic success. Three major themes were found: (a) the culture of Latino males has an impact on the dropout rate; (b) suspension has an impact on the dropout rate, is ineffective in preventing unwanted behavior, and school principals do not have any specific programs to combat suspension; and (c) school principals do not have any specific programs to combat the dropout rate in their respective schools. The findings of this study suggest that a future study should be conducted on designing public schools that promotes the unique academic needs of Latino males in urban settings.