For decades, Asian Americans have been characterized as a "model minority" due to perceived success in educational attainment and labor market outcomes. However, there are concerns that Asians remain underrepresented in top level positions in the workplace. This study presents new evidence on the extent of this underrepresentation between US-born Asian American and White men and examines mechanisms driving racial leadership gaps. Results indicate that Asian men are significantly less likely to work in management and executive positions compared to White men with similar qualifications. However, Asian men are not underrepresented in other high-paying, non-leadership occupations, suggesting this is a phenomenon unique to leadership occupations. Furthermore, these gaps are only present among East Asian and Southeast Asian men, while South Asian men do not differ from White men in the likelihood of working in leadership occupations. I examine several mechanisms and find no evidence that gaps are driven by racial differences in preferences for leadership positions, selection into self-employment, intergenerational transmission effects, immigration recency, or ethnic attrition.