The disproportionate, over-representation of Black boys in special education continues to be a matter of social injustice and inequity in education. Many Black students are placed in special education due to subjective identification processes. This is especially true when it comes to classifications such as Emotional Behavior Disorders (EBD). Black boys classified with EBD are more likely to be educated in exclusionary settings, and once placed, are less likely to return to integrated environments. This often leads to poor educational and life outcomes. The topic of disproportionality in special education has been studied and discussed over the past several decades, yet the problems persist. The purpose of this article is to discuss reasons for the over representation of Black boys who are identified as having EBD. Moreover, this discussion is extended to include the disproportionate, under-representation of Black men as special education professionals, classroom teachers and full-time faculty members in special education teacher preparation programs. The impact of this juxtaposition continues to exacerbate both sides of disproportionality of Black males in special education.