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While sociologically significant, gender and masculinity remain under-examined constructs within interventions focused on keeping youth safe from violence and free from carceral contact. This study will focus on how gender and masculinity operate within the credible messengers initiative in Washington, D.C. More specifically, this presentation will focus on the lived experiences, roles, and dynamics among the frontline workers who work with structurally vulnerable youth. Often criminalized Black men and masculine identifying persons, they perform critical life-saving forms of care work, which frequently contradict hegemonic notions of masculinity. Using interviews and ethnographic observations, this presentation will focus on how these men challenge prevailing notions of carceral masculinity, often depicted as static, hypermasculine, and “hard.” Instead, these men display “softness” and empathy in their work with youth and each other. Black masculine empathy and relatability are presented as valuable and historically rooted concepts to rethink criminalized and carceral masculinities. The presentation will also include a series of policy and practice recommendations for these interventions.