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Predictable racial disparities within the United States continue to exist in every sector (e.g. healthcare, education, incarceration, etc.) (e.g. Skiba, et al., 2011). White supremacy and racism fuel these outcomes (DiAngelo, 2012). Therefore, this case study focuses on the efforts of one principal who created a series of conversations about race for a small group of middle school students and their assigned adult mentors. Data sources included: artifacts, field notes from meetings, transcriptions from meetings, and interviews of adult mentors and students that were audio recorded and transcribed verbatim. Initial data analysis revealed the following three themes: (1) demand for inter- and intra-racial dialogue; (2) the necessity of strategic planning; (3) "collaboration" with a White gaze continues to center whiteness.