Black women leaders in higher education face a double bind of gender and racial disparity and biases within the education workforce and their institutions. The literature does not fully articulate Black women's considerations when pursuing community college presidencies and the strategies they use to overcome the hurdles and discrimination they encounter. This research expands the literature by using critical race and Black feminist thought as theoretical frameworks to examine the ascension and succession of eight Black women leading community colleges and how they circumvented barriers associated with the male-dominated position. Findings reveal how three elements of resiliency--emotional intelligence, authenticity, and agility--contest and challenge the oppressive nature of White male privilege in gendered organizations. This newfound perspective has implications for the recruitment, retention, and persistence of faculty and administrators, leadership development programs, and succession planning at community colleges across the United States.