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This paper focuses on three long-term teachers, examining why they continue to teach when national trends place them in the minority of all teachers. I story their teaching and non-teaching lives, and then consider how some of the research on teacher retention speaks to their individual cases. There is an element about these teachers, though, that is not seen in the literature: teacher rootedness, in both living and teaching. I argue that all three teachers are rooted in their communities—at home and at school. Further, as a result of these roots, they teach students about cultivating roots. I posit that discussions about and study of teacher retention need to be informed by attention to the integrity of teachers’ lives.