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Breaking stereotypes and changing generational outcomes for Black and LatinX students requires culturally competent educators able to be “good trouble makers” with the communities they serve. Culturally informed educators can have a transformative effect on their students, but what impact does the CDF Freedom School teaching experience of Servant Leader Interns (SLIs) have on young educators themselves? CDF Freedom Schools foster professional learning communities with novice teacher interns committed to the lives of children, and the potential of community organizing. The CDF Freedom School in South Los provides an example of a successful partnership between the national consortium of CDF Freedom Schools, and a local nonprofit organization dedicated to leadership development and community organizing among Black and LatinX families. Four years after participation, the personal stories of former SLIs reveal the longitudinal impact of participation on the community as well as their leadership journeys and career trajectories.