Drawing on longitudinal ethnographic research carried out over two-and-a-half decades in barrio Luis Fanor Hernández, a poor neighborhood in Managua, Nicaragua, this article explores how legal and illegal economic activities are socially legitimized, and more specifically, how certain illegal economic activities can end up being seen as legitimate, and certain legal ones perceived as illegitimate. The first part of the article explores the variable morality surrounding different types of criminal activities that local gang members engaged in during the 1990s and 2000s. The second part considers my experiences running a local market stall, describing the contrasting reactions I faced when I resorted to first legal, and then illegal, strategies to boost my revenue levels. Taken together, these examples showcase how the social legitimization of an economic activity has less to do with whether it is legal or illegal, but rather the future aspirations it embodies.