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In this chapter, we report on a qualitative research project on which we worked closely with members of a youth-run community organization to explore racialized and marginalized youths’ experiences with and perceptions of school discipline, police, and the legal/justice system. Data came from individual interviews, focus groups, as well as rap and hip hop workshops. Utilizing critical theories, we discuss the challenges of conducting respectful research with marginalized youth and our experiences and efforts to conduct research that moves beyond merely having youth tell their stories to having them work with the research team in ways that enable them to develop useful skills and learn about their legal rights and responsibilities. In our efforts to engage in culturally responsive and relevant research practices, we sought to build trust, honor community, and support the youth through collaboration and reciprocity. We argue that understanding and supporting racialized “at-risk” youth requires that we also question and modify our methodologies to consider a range of approaches that are not only relevant and familiar to researchers, but also relevant and responsive to respondents and their community’s cultural, social, educational, and political needs and concerns.

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