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Since World War II, it seems like the result of America’s participation in war has fallen short of our goals. We enter with the best of intentions, seeking a low cost, swift conflict and an overwhelming victory without excessive casualties (American, civilian or even enemy). During the opening stages of these conflicts the overriding question seems to be “what is the exit strategy?” Muddled in there may be an idea of what victory might look like. We seem reluctant to ask, “How do we win?” and instead wring our hands saying, “Tell me how this ends.” This paper discusses how for American policy makers and military leadership, understanding war as a wicked problem is the first step necessary to reframe our understanding and response to the need to use military force.