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Alternative schools fall in an interesting space of being able to provide innovative and supportive opportunities, different from mainstream schooling, yet also alternative schools are part of a mechanism for sorting youth. Labels of “at-risk” often become assigned to youth that exist at the margins of educational systems, youth who do not fit into predetermined and reified definitions of success. For youth in alternative schools, identity development becomes, in part, navigating and redefining risk. This paper is a case analysis of identity development of one youth’s experiences with risk as he entered into an alternative high school. Findings focus on youths’ previous experiences with risk, redefining risk and creating safe communities, and leveraging risk to support identity development.