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Studies of development assistance in Afghanistan have found the impact of such assistance for reducing violence and countering insurgents to be weaker than in Iraq, not connected to improvements in Afghan perceptions of the quality of their governance, and inconsequential in the long term. While these previous results seem disappointing, existing frameworks offer only a limited perspective on why development assistance has not been more impactful in Afghanistan. My research analyzes development assistance in contexts that are more closely related to the reality of how insurgents fight within the geographic environment in Afghanistan compared to the existing literature, while also focusing on the longer-term effects of assistance rather than the short-term impacts previously examined. My framework identifies the concepts of risk and commitment as critical factors for countering insurgents. Risk refers to the risk tolerance for counterinsurgents, specifically the degree to which counterinsurgents emplace development assistance in areas that favor insurgent control. Commitment refers to the persistence of efforts aimed at development assistance, capturing the period of time over which counterinsurgents make investments in a local area. My empirical work coupled with qualitative interviews indicate that counterinsurgents must be willing to take risk and demonstrate commitment for development assistance to contribute to stabilizing a local area. An implication is that the weakness of development assistance for countering insurgents in Afghanistan reflects the typical situation in which development assistance has high commitment but low risk. Even when development assistance has taken risk, sporadic commitment might be constraining the effects. A hopeful implication of my research is that when development assistance involves sufficient risk and commitment, it has the potential to reduce violence in an adjoining area. In particular, I find that more risky rural development has a consistent association with less urban violence, while less risky urban development has a consistent association with more urban violence. However, the requirements of risk and commitment are steep in practice. It is possible for development assistance to reduce violence and improve stability, but the institutional headwinds are great and the costs—no matter the dimension in which they are measured—are substantial.