Community teachers, particularly those who are Black and Latinx, are assumed to improve retention and outcomes depending on retention in schools that serve low-income Black and Latinx students. Based on a critical quantitative analysis of data collected on the career trajectories and retention of hundreds of alternatively certified mathematics teachers, the study shows that community insiders exhibit significantly higher rates of retention in district schools than community outsiders and, in particular, those from elite colleges. Utilizing quantitative critical theory methodology, the study helps to move the field beyond race-neutral analyses of teachers' retention and careers.