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The sustained equity-oriented district transformation agenda of one large urban school district in the Northeast presents a unique opportunity to study how a district can bridge theory and practice to change racial inequities. In noting this, I ask: What contradictions arise during an equity-oriented district transformation process? This paper draws on school leadership and district-level change literature. I employ activity theory while investigating through content analysis the contradictions that arise from a yearlong professional learning series about racial equity. The data suggest two primary contradictions - transforming toward racial equity while engaging in accountability and the personal discomfort when discussing race or racism while working in a culture of niceness. Implications for leadership and preparation are discussed.