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This study explores how historically marginalized leaders conceptualize leadership for social justice. It examined interviews with seven administrators in Ontario and found that racialized and LGBTQ+ leaders’ experiences of injustice impacted their orientation toward leadership for social justice. The findings suggest that: 1) HMLs are essential in addressing discrimination within schools; 2) new paradigms are needed in leadership that focuses on engaging HMLs’ experiences; and 3) HMLs lead differently and go beyond what is taught in textbooks, thus necessitating them to be termed “Vanguards.” Core to the findings of this study was that Vanguards hold the potential to identify ways in which structural racism and discrimination operate in education and that this knowledge may lead to decolonizing educational administration.