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Motivated by growing concerns over police executive turnover and its associated costs, this study investigates how individual, organizational, and political factors shape the tenure of police executives in the 98 most populous U.S. cities over a 30-year period. An original dataset of police executives was compiled using archival records, public records requests, and media sources, combined with multiple waves of the Law Enforcement Management and Administrative Statistics (LEMAS) Survey. Findings suggest tenure is shaped by both individual and institutional characteristics. The study aims to inform selection and retention strategies and contribute to broader conversations on police leadership, offering practical insights for departments and policymakers seeking to reduce turnover and understand the factors that contribute to executive stability.