Increasing racial and gender diversity has been an urgent goal in many professions and education is no exception. Though the call for more Black men is a worthy one, many challenging questions arise when one considers the country's socio-historical record. The purpose of this study is to explore some of these questions that arise as one probes the call for more Black men in the teaching profession, particularly as these questions relate to their racial and gendered identities. Using intersectionality as a conceptual framework, interviews of seven Black male secondary special educators in New York City public schools are analyzed by employing grounded theory methods and invoking the African-American oral tradition via narrative inquiry concepts.