A growing concern around gender and race inequality in leadership has increased research interest in marginalized groups of society, with the aim to understand different ways in which the attainment of social justice in corporate leadership can be reached. However, research in this area tends to focus on women’s experiences, while men’s views and experiences remain under-researched. On the surface, the combination of patriarchy and masculinity smacks of privilege and power, yet, an intersectional analysis disrupts that privilege. This chapter draws on a subset of life history interviews that explored constructions of masculinities and leadership among Black men in transnational corporate leadership. It uses two Black male participants’ life histories as case studies to disrupt whiteness and the prototypicality of Black women as subjects of intersectionality.