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This phenomenological research study centers Children’s Defense Fund Freedom Schools as a model for engaging youth and disrupting inequitable educational experiences. More specifically, this paper delves into the lived experiences of a single Servant Leader Intern (SLI), at a Freedom School in the southeastern US. We gained insights into how his personal background uniquely informed and enhanced his interactions with scholars and their overall contributions within the Freedom School setting. Highlighting themes of intergenerational and cross-cultural learning and the challenging of learned narratives this study helps to better understand the lived experiences of SLIs and the role of representation across formal and informal educational contexts in support of underrepresented students.