Purpose: Many US school districts currently face teacher-retention issues, raising questions about which new teachers might remain long term in district schools. Positing that a teacher's local ties matter, this quantitative analysis was designed to compare the long-term retention of community-based teachers to community outsiders in the school district that recruited them and subsidized their initial training. Research Methods/Approach: To understand the extent to which individual preparation approaches might distribute different retention benefits to different teacher subgroups, the study examined teacher preparation as an interactive system. Drawing on administrative data from New York City Public Schools and project survey data, the study used logistic regression to model the 3-, 5-, and 8-year retention of 617 secondary mathematics teachers who entered teaching through a high-profile alternative teacher-certification program. Findings: Community insiders--defined in this study as the graduates of New York City high schools--had markedly and significantly estimated higher odds of district retention than that of community outsiders at all three points in time. Black community insiders who entered teaching with prior career experience were shown to have particularly high odds of retention in the district. Implications: The results indicate that the recruitment and development of community-based teachers, and particularly those who are Black career changers, promise to improve retention in district schools. They also support the thesis that retention and other program-level outcomes are the product of interactions between certain types of teachers working in particular (e.g., highly racially segregated) schools and the initial training they receive in teacher-certification programs.