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The denial of childhood innocence for Black boys is evident in their educational experiences and compounded by systemic abuse in the U.S. Using the frameworks anti-Blackness, Black feminism, and childhood studies, my research explores how Waldorf philosophy and pedagogy can nurture this innocence. I applied Maisha Winn’s Transformative Justice in Education framework and the Five Pedagogical Stances to analyze Black boys at Milwaukee’s Urban Waldorf School (UWS). This study employs portraiture, an art and science methodology developed by Sara Lawrence-Lightfoot, to draw from 15 semi-structured interviews with former UWS educators, students, and a researcher. I assess whether Black boys’ experiences at UWS align with the Waldorf promise to preserve childhood innocence and promote transformative schooling.