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When institutions of higher education (IHEs) are contextualized, we see how dominant characteristics influence institutional decision-making that directly impacts the lives of learners, faculty, staff, and its community members. This paper applies neoliberalism, community cultural wealth theory, and plantation politics as frameworks to analyze the socio-cultural-political trends of American higher education. IHEs need to uncover, name, and disrupt implicit and explicit dominant characteristics to create life-affirming institutions that support all its stakeholders, especially those from historically marginalized communities. In this paper, critical storytelling is used as a methodological approach to explore lived experience to problematize dominant characteristics embedded in institutional culture. Three perspectives will present how leaders of color who are first-generation re-negotiate political spaces in positions of power-dynamics.