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Since the 1960s, U.S. higher education access has expanded for historically marginalized groups, including along lines of race and ethnicity. Yet people of color remain underrepresented among faculty and academic leaders. This paper examines when, and through which mechanisms, historically White institutions (HWIs) as racialized organizations appoint their first Black presidents. Drawing on a nationally representative, longitudinal sample of 224 four-year HWIs from 1980 to 2018, we identify both descriptive trends and institutional predictors of Black presidential appointments. Findings highlight the significance of prior diversification within executive leadership and mimetic pressures across the sector. We discuss these findings in the context of literature on racial representation in higher education leadership.