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What explains variation in leaders’ risk of punishment during and after civil war? This paper examines two factors thought to affect leaders’ risk of punishment: the use of terrorism and engaging in negotiations. Counterintuitively, this paper argues that engaging in terrorism actually increases certain leaders’ longevity in power, while negotiating with the opponent has the opposite effect, conditional upon the group’s organizational structure and leader characteristics. Expectations are tested using original data on the fates of all leaders engaged in civil conflicts between 1980 and 2011. This paper has implications for understanding why certain leaders refuse to engage in negotiations despite the potential benefits of doing so, and why certain leaders engage in terrorism despite its potential negative effects on prospects for victory.