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This presentation considers what it means to be an Asian/American dean with critical politics, while negotiating the inherent limitations presented by institutions of higher education. Drawing on the theorizing of Asian/American racialization established by Day (2016) and Lye (2008) and using the counter-narrative provided by my own biography, I tell the story of how I came to campus leadership from a bottom-up, activist-service approach defined by situational, institutional politics combined with my own radical politics. In this context, I reflect on how institutions of higher education inherently push administrators towards conservatism, and I think through how these inherent limits have contributed to my ongoing successes and failures as a dean who seeks to maintain his political integrity. Ultimately, this presentation addresses the role of higher education in reproducing gendered and raced social relations and raises questions about the limits and affordances of equity work within such educational contexts.