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Police leadership in Canada is in turmoil. Police leaders appear to be turning over at an alarming rate, jeopardizing the stability of police services and raising questions about recruitment and retention by police service boards and commissions. In this study, we examine police chief tenure in 41 jurisdictions across Canada over the last 25 years. Using survival analysis, we seek to determine if the rate of police chief turnover is indeed increasing and, if so, which factors contribute to these changes. At the same time, we aim to determine which factors contribute to police leader retention. This research has implications for police leadership in Canada and internationally, by contributing to important conversations about the role of police leadership for police organizations in the 21st century.