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The West Side Boys were one of several military actors in the Sierra Leonean civil war (1991–2002). A splinter group of the army, the WSB emerged as a key player in 1999–2000. In most Western media accounts, the WSB appeared as nothing more than renegade, anarchistic bandits, devoid of any trace of long-term goals. By contrast, this article aims to explain how the WSB used well-devised military techniques in the field; how their history and military training within the Sierra Leone army shaped their notion of themselves and their view of what they were trying to accomplish; and, finally, how military commanders and politicians employed the WSB as a tactical instrument in a larger map of military and political strategies. It is in the politics of a military economy that this article is grounded.