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Does decapitating the leadership of an opposing state have a significant effect on the outcome of interstate war? States currently seem more capable and willing to target leaders, even in interstate conflicts, but there is limited work on the effectiveness of this strategy within interstate war. Most literature on leadership decapitation falls into three categories. The first discusses the threat of losing large portions of a government via nuclear weapons, the second focuses on non-state leadership decapitation in the past two decades, and the third examines the strategic applications of decapitation in interstate warfare during the 1980s and 1990s. However, none of these bodies of literature draw from a complete dataset of leaders lost in interstate warfare to examine the relationship between leadership decapitation and the outcome of an interstate conflict. To address this issue, this paper uses a newly compiled dataset containing a list of generals, admirals, political leaders, and heads of state lost in interstate war. The paper uses this data to examine the effects of leader loss and leadership decapitation in interstate war in a three-step process. First, I examine the effect of losing a leader on the outcome of war across levels of seniority. Second, I use matching to determine the effect of using a decapitation strategy. Third, I examine the effects of decapitation attempts that kill or capture a leader, as well as attempts that fail to do so, across seniority and regime type. The results indicate that the loss of senior leaders is associated with changes in the outcome of war that favor the opposing state. These effects are more pronounced when states deliberately target leaders, as successful decapitations tend to provide significant benefits to the targeting state. Additionally, the effect of decapitation is greater when power is more centralized and when there are fewer viable replacements. As a result, leaders that are more senior, autocratic, and neopatrimonial make better targets, as the loss of such leaders tends to result in more strategic confusion in the targeted state.