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Alarmingly high rates of teacher attrition exist in contexts designed for students with considerable needs, such as in alternative education programs serving marginalized youth. Research has linked teachers’ levels of motivation and well-being to their effectiveness and retention. Consequently, we explore what distinguishes teachers who thrive in contexts others find taxing. Specifically, we investigate whether and how their motivation and well-being support their teaching effectiveness. As part of a larger case study of an alternative education program for youth who haven’t found success in mainstream schools, this article reports a semi-structured interview asking whether and how one teacher’s perceived autonomy, belonging, and competence support other facets of his motivation (e.g., teaching efficacy) and his well-being (i.e., constructive responses to potentially stressful events.) Plentiful evidence was found to link our researcher-derived constructs from self-determination theory to the teacher’s professional experiences in general, and to his work with youth in particular, indicating that our conceptual framework is an authentic representation of his experience. Implications for theory and research are discussed.