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This study examines the New York City Department of Education’s citywide implicit bias initiative, which set out to engage 130,000 employees in reflecting on and addressing their own biases. Drawing on news coverage, internal training materials, and interviews with four school leaders and four racial justice facilitators with longstanding commitments to racial equity, the analysis surfaced a complex set of responses. Participants largely described the trainings as superficial and diluted, falling short of their intended impact. At the same time, they acknowledged the scale of the effort, recognizing the initiative’s reach as both unprecedented and potentially generative, signaling a possible starting point for deeper antiracist and abolitionist transformation within the nation’s largest school system.