Have you ever thought about the potentialities coming about if Michael Jordan chose to emulate previous figures such as Muhammad Ali, John Carlos, and Tommie Smith regarding social activism? Michael Jordan has often been criticized for his failure to speak on social matters. Like Jordan, contemporary Black male athletes’ engagement in social activism has been minimal, unmatched to that of their predecessors of decades ago. The article employs transformational leadership principles and social cognitive theory (SCT) to analyze the link between Michael Jordan and the lack of Black male athlete activism in the current era. Implications for current and future generations of Black male athletes are discussed. Future research directions are also presented for scholars interested in Jordan’s impact on Black male athlete activism.