The participation of the young toughs in the Sierra Leone civil war (1991-2002) presents an opportunity to better understand the complex interplay of context and agency. Young toughs are criminal, undereducated, unemployed and unemployable. They lack community and familial ties, and are void of political sophistication. As such, they are a detriment to political stability, economic prosperity and development. Their criminal existence and violent behavior are often blamed for the failure of sub-Saharan Africa. In this sense, they resemble the archetype of the African savage construct. How did the post-colonial landscape shape their status as young toughs and what trajectory does their social exclusion take, particularly in relation to the conflict? It was this group, the disenchanted youth-turned-combatant that was primarily behind the more heinous RUF attacks on non-combatants: the hacking of hands, arms, lips and ears. Why did young men pick up machetes and attack the civilians they purported to fight for? They were not fighting for religious freedom or ethnic grievances. Instead, they were fighting because they weighed their options and brutal conflict seemed more attractive than life as a young tough.