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This study examines the youthwork paradox in community-based education spaces (CBES), where efforts to support Black youth and youth workers can simultaneously reproduce and resist anti-Blackness. Drawing on Christina Sharpe’s (2016) concepts of the Wake and Wake Work, the concept paper reframes the youthwork paradox as part of the afterlife of slavery. Using Critical Interpretive Synthesis (CIS), the analysis engages existing literature on CBES to trace how the logics of slavery persist and theorize about the ways Black communities engage in acts of resistance within out-of-school learning organizations. Findings highlight the potential to utilize leadership theory to study how Black leaders reproduce and resist the youthwork paradox.