For many decades, society has struggled with academic underachievement, particularly among African American males. Although a myriad of studies have identified significant causal factors of African American academic underachievement from the perspectives and circumstances of the student, limited studies focus on this problem from the perspective of the educator. This nonexperimental, descriptive quantitative study permitted an examination of the perceptions and cultural interpretations of educators who teach African American males. Questionnaires assessing perspectives and cultural interpretations of teaching African American males were completed by 170 educators in elementary and middle schools in New York City. Participant responses were analyzed to determine perspectives on teacher training, cultural exposure outside of school, racially sensitive experiences, and instructional practices. The findings of this study show that 86.2% of the surveyed population indicated they believed that understanding the culture of a student is essential to academic success, yet 81% of the participants indicated they learned most of what they know about African American males through professional experiences. Additionally, less than half of the participants strongly or somewhat agreed that formal educational training adequately prepared them to service African American male students. Further research might examine the effects of personal interactions with African American school-age males on educators' perceptions of this population or the effects of educator perspectives on educating African American males. There is also a strong need to examine how cultural sensitivity, especially towards African American males is addressed through teacher training and professional development.