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Do the attributes and experiences of individual rebel leaders shape the outcomes of civil wars? In recent years, a substantial literature has explored the impact of organizational factors as well as broader country- and conflict-level characteristics on civil war dynamics and outcomes. In this paper, we add to the literature by focusing on the role of the individuals who lead rebel groups and how their backgrounds shape their willingness to make peace or fight on. In particular, we argue that leaders’ age and combat experience shape their openness to negotiate a peaceful resolution to a dispute, with older and more combat-experienced leaders more likely to reach a negotiated settlement rather than to fight on because they have a keener sense of the costs that the conflict has visited on their communities. We test this argument with data from the newly constructed Resistance Organization Leaders (ROLE) database, which contains a variety of information on over 500 rebel leaders active in civil wars from 1980-2011. We find robust support for our argument, with age and combat experience both boosting the odds of a negotiated settlement. In addition, we find that these effects are especially strong for disputes that are longer-lasting and see greater levels of violence, supporting our costs-of-conflict based mechanism. These findings offer new policy insights about the opportunities for negotiation with rebel organizations, while underscoring the importance of individual rebel leaders as a key unit of analysis in conflict studies.