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Is capturing and killing insurgent leaders a shortcut to success in counterinsurgency? In this paper, I develop a theory to explain the effects of leadership targeting that revolves around the key question of how leaders are replaced. I argue that the structure of the targeted groups, the roles of the targeted leaders, and features of the targeting campaign all influence the ability of insurgent groups to replace targeted leaders, and therefore, determine how effective leadership targeting will be. I test the predictions of this theory using an original dataset of leadership targeting against insurgent groups in Iraq in the years following the 2003 US-led intervention, as well as qualitative evidence from both government and insurgent sources in this conflict.