This paper is based on two ethnographic studies. The first was carried out between 2011 and 2013 in a barrio of Guatemala City, the capital of one of Latin America’s most unequal countries. Still ongoing, the second is being carried out in a working-class neighborhood of Milan, Italy’s richest city. The paper will illustrate a qualitative, non-objectivist, and non-generalizable comparison of the “deviant careers” of three adolescents (two Guatemalan and one “second generation” Italian) who have each been in contact with local youth gangs. Though living in two structurally-dissimilar contexts, the three youngsters drew from a partially-shared global imaginary to structure their representations. “Refusing delinquency” constituted a common action strategy at some point in their lives, but subsequently led to very different trajectories.